This is the full text of my guide on writing resumes and cover letters as a creative generalist. Since writing and launching this book, a lot has changed and some of the content needs a bit of a refresh. I'm not planning on doing that so have shared the entirety of it to read here for free. Take what resonates and leave the rest. 

This is not your average resume and cover letter advice book, let's make that clear off the bat.

I wrote this for people like me. If you're a non-technical creative or a generalist, then this is for you. Whether you're looking to change careers or are new to the working world, then this is also for you.

I'm sure you know all the standard resume advice. And if you don't or you're not sure (after all, if you really did know it all, then shouldn't you have a much better success rate?), well, you'll get a refresher. But this is more than "how to write a resume". Almost anyone can put together a resume. The information is out there for you to find. Even so, you might be surprised just how many people disregard the basics. It's not that easy after all.

After writing and reading lots and lots of resumes, I've seen first-hand how challenging it is to write one really, really well. I've also seen first-hand how a well-crafted job application package can really make a standout candidate.

One of the reasons is because people who dole out resume and career advice are often working in the field. Career advice or hiring is their industry. It's not mine. My "industry" is technology and the creative world, fashion, maybe media depending on what season it is in my creative life. Honestly, I'm not really sure what my industry is; I kind of cross over into a lot of things.

My point is: when careers or hiring is your industry, the advice you give gets people to a B grade. You're getting people to a nice, polished standard. You're not necessarily getting them to next level.

And next level is what people like you and me need. I come at it from a cross-disciplinary perspective, with hiring and leadership experience. I know what hiring managers and employers are really looking for, and I know what it takes to stand out as a creative and as a generalist. This is the sort of nuance that you don't usually get from your typical resume and cover letter expert, unless perhaps you were to hire one to do it all for you for a few hundred or more bucks. You might get this sort of advice from a recruiter, if you're in the position to be working with one, and if they're really good at what they do, and that's not a privilege that many early career people have. And it's for the same reason: they have a financial incentive to get you the job, so they're willing to take the time and effort to help you get it.

Me? My incentive is that I wrote this book and you've paid for it. The purchase has been made and now it's up to me to provide you with genuinely useful and valuable information. I did price this book so that it's accessible. I also wrote it so it can easily be digested in one sitting. I'm here for that whole "teach a person to fish..." thing. You shouldn't have to rely on someone else to sell yourself. You are your best salesperson. Or, you could be soon.

Just so you know a little bit about me and where I'm coming from, I didn't stand out in the traditional ways: no fancy school, no big names on my resume early in my career, certainly no awards or a portfolio to show off, and in fact, I was both a career changer and early in my career.

I graduated with a vocational degree (meaning: the skills I learned were ultra-practical but also ultra-specific to one very narrow career path and industry). I had what I thought was a quarter-life crisis soon after, when I realized that what I spent 4+ years of full-time effort on wasn't what I wanted to do after all.

Turns out, it wasn't so much a quarter-life crisis as it was an ongoing one, only resolved through action and a few strokes of luck in jobs that ended up being really good choices. Calling it a quarter-life crisis kind of downplayed the whole thing as a temporary nuisance set on by the natural progression of adulthood, removing my sense of agency in the process. But I did have more choice and agency than I led myself to believe I had at the time.

My one advantage? I've always been a good communicator and I kept learning, testing, improving even as I was stuck in the midst of a years-long career rut. I started from the ground up, actually—working a now less-than-minimum-wage job for years. I became a self-taught marketer and copywriter and used the same skills and psychology I learned to help brands to help sell myself. It worked and I finally got out of the cycle of entry level work, eventually making over six figures, me with my community college fashion degree.

I mention the money even though there's a part of me that has it ingrained that talking about money is tacky. But I know that there are a lot of people out there who relate to this: the worry that all they'll ever do is entry-level work, that they'll never make more money than they do now, and because of that, that this, whatever situation they're in, that this is it and it's not going to get any better. You can call it a rut but we both know that some people stay stuck in it forever.

A better resume and cover letter isn't just about getting the job. It's about getting the job you really want. The job that pays more. The job that helps you build your career and leads to other jobs, opportunities, chances. It leads to more bets you can take on yourself.

Money isn't everything, but it's more important than many of us would like to admit. Money is one form of power, independence, influence, visible and invisible.

My approach to resumes and cover letters is about rerouting the way you think about yourself and the way you think about work, period. Thinking about everything in terms of value and impact will not only make you a better candidate for the job, but a more valuable player at work, in any job. It's the kind of behavior that has the power to exponentially expand your future and its possibilities.

Yes, every job is just a job at the end of day. You can walk away from it, always, and your job doesn't define you. There will always be more. But a great job has the ability to impact your life more than almost anything else you can do to improve your life.

This book is tiny. It clocks in at just under 30,000 words, which is pretty bite-size. That's the point. You can probably read this in about an hour. But it's dense, it's practical and it's going to be an hour of information that I hope might just change your life.

I do want to share a fair warning with you: as much as this is about getting results, you'll also learn about why great resumes and cover letters work the way they do. Why? Because understanding why helps things stick better and builds a stronger muscle for long-term retention. Having concepts ingrained makes you more efficient every time you need a resume or cover letter, which saves you time, which means that you're making more money per hour, all things considered, when it comes to the amount of time you spend in a job but also looking for it, applying for it, and interviewing for it. The interview process is long and tedious enough.

Why a book on resumes and cover letters? You may have heard people throw around "Websites are the new resume", "Blogs are the new resume", etc, etc, etc. I've thought about this long and hard. Maybe it's worth writing about websites and online presence as well, put it all up together as an all-inclusive guide to packaging yourself .

But, I've read thousands of resumes and so many people don't even have the basics down. If your resume and cover letter doesn't do the job, no one's going to even bother with your website.

I also wanted to make this information as accessible as possible. I think that a great resume and cover letter (free to create) will take most people much further than a mediocre website. With the rapid changes in the internet economy, resumes and cover letters are still the standard.

(That said, I've included a chapter on what to do once you've fully optimized your resume, including advice and tips for building your own personal website.)

Resumes have come a long way since their first recorded appearance in 1482 by Leonardo da Vinci, bonafide creative and Mr. Generalist Extraordinaire himself. At 30, he wanted to find work in Milan as a bridge designer, boat builder, or sculptor, and wrote the following which he sent to the Regent of Milan. (It's written in Latin, but translated, the point is pretty much "hire me!")

Leonardo da Vinci's handwritten resume, 1482

It seems fairly certain that perhaps there were other such resumes but perhaps no example as famous as this, so Leonardo's is generally thought of as the world's first resume, even though technically it's written more like a cover letter.

By the 1930s, resumes were commonly written on scraps of paper (still handwritten, of course) before becoming stat sheets in the 1940s that included details like weight, age, marital status and religion. A decade later, they entered the mainstream. The next fifty plus years saw word processing, VHS resumes, and fax machines all play their part in the modern resume. And then along came the internet, email, LinkedIn and social media.

The cover letter also started becoming popular around the 1930s, though its value has been the subject of debate in recent years. So do you even need a cover letter anymore? We'll get to that.

I've seen a lot of changes over the years when it comes to the job hunt process. As much as things have changed, the resume and cover letter have largely remained the same, except one really important detail, which we'll also get to in a bit.

My mom was my first resume "client" (JK, she didn't pay me) when I was about 11. She had raised four kids in a single-income household and when my youngest sister was old enough for kindergarten, it was time for my mom to go back to work. She took a program to change careers from "homemaking" (this is actually what she put down as her job) to insurance sales after a long hiatus from the world of paid work.

I remember proofreading the scant document, unsure of how to make it better. She had a law degree in Taipei, worked with computers in the 1970s even (as a kid this was the year we got our first computer, so it was quite the shock of my life to hear that my mom had worked with them decades before)—but I had no sense of what she did.

I did the best my 11 year old self could, but I don't think it worked because for whatever reason, her career change didn't pan out and she instead switched gears to an entirely new career a few months later and became a self-employed driving instructor for the next twenty years.

This was when resumes were sent in envelopes through the mail, in person, and our very loud and very beige fax machine.

It's now been more than two decades since my first resume edit and I somehow became the go-to for many of my family and peers, with a much better success rate.

I didn't think much of this skill other than a way to help people out until three things happened:

1. I started hiring for jobs.

2. I started learning about inequities and biases in hiring, the workplace and leadership.

3. I started to work with a lot of high-impact, creative people who struggled with finding jobs that paid well. At the same time, I was one of these high-impact, creative people who didn't feel any less valuable than the people I worked with who were making a lot more money than I was.

These three things together started to simmer in my brain. I watched people get paid multiple six figure incomes, who weren't necessarily any smarter than the people making close to minimum wage. And yet, they had more sway, more influence, more security. Their lives had a lot more mobility. They had the ability to create future generational wealth while others seemed destined to repeat cycles of near-poverty.

I watched companies get whiter and more male the higher up the company hierarchy you got, sometimes not in obvious ways but in a way that was pointedly obvious when salaries came into the picture. I saw promise in people and efforts to diversify the workforce of these high salaried roles with programs, content and initiatives to help more women and people of colour get into software engineering, for example. When the Black Lives Matter movement came to a crescendo in 2020 during the height of a worldwide pandemic, these efforts became more urgent and more prevalent. And yet, I couldn't help but feel that there was still something missing.

I hated the idea that in order to be higher paid, more impactful and more valued, you have to choose a certain narrow career path. I hated the idea that the picture of diversity is focused on bringing more diversity into specific roles that are already seen as valuable and impactful, rather than to consider that there may be value and impact in other places all along, and that we should be working harder to demonstrate value and impact in ways that can be quantified and measured.

I made a rule for myself a few years ago, when I realized how much time I was wasting on wishing how things were different: if I catch myself thinking about something over and over again, I either have to do something about it or I have to just let it go.

So this is me doing something about it, through my trade of choice: writing.

This is a resume and cover letter guide that doesn't ask you to change who you are in order to get a better job. It's not going to ask you to choose a career path to stick to as your only route to a higher salary and career success.

Instead, it's going to ask you to figure out what your "story" is and how best to sell that story in a way that demonstrates your value and impact. It's going to take who you already are and make you much more valuable to hiring managers.

Notice I've been throwing around the words "value" and "impact" around a lot?

That's because these are very important words when it comes to this whole conversation about making money, getting jobs and building a more equitable and diverse workforce and world. And I want you to start thinking in this way too. Rather than thinking of yourself as a set of skills lumped into a person, retrain yourself to think of yourself as someone who achieves outcomes and gets the right things done. Your skills? They're just a path to outcomes.

And the outcome we're all trying to achieve together is broadly a better world. No one really wants to make the world worse than it is. Most of us just don't think we have the power to. But what powers the world? The companies in it. What powers the companies? People.

Unfortunately, the generalists of the world are the people who usually have a slightly harder (or much harder, in some cases) time getting jobs when starting their careers because it's hard to put them a box, it's hard to know how impactful they can be, and it's hard to know what exactly they're going to do to contribute to the bottom line.

But when rightly cultivated and when encouraged to use their skills, these are the people that might just save the entire system of work. It's a tall order yes, and I'm not going to dive too deeply into this but I've included some resources in the appendix, if you want to learn about what generalists are and why they're going to become so much more valuable over the next few decades, starting right now.

This tiny book is about helping people get better jobs, waste less time, and make more money immediately and in the long run. It's not very creative in the sense that it's a book and you know how those things go, but underneath it all, this is a very creative resume and cover letter guide. (At least, I haven't read another one that offers resume advice alongside musings about the impact of technology and the patriarchy of industrialism.)

It's a different way to think about how you package yourself, updated and written for the job hunt and climate right now. By helping more people discover and communicate their value to suit the needs of companies today, we can start to shift entirely the way we perceive who we are, what we can do, and how others see us too.

And that starts with a little bit of prep work.

Hello world, preparing for the job hunt

Forget about best practices, you're here to stand out

Standard resume and cover letter advice is centred around best practices. Best practices is a misleading term because it really just means average practices. When you're applying for a job against dozens and maybe even hundreds of other applicants, average is only enough to land you in the "maybe" pile. Even if you follow all the standard tips, you'll only get as far as the top of the maybe pile.

The maybe pile is the worst pile to be in. Lukewarm. Neutral. Not good or bad enough to be memorable either way.

Being memorable means making an impression. That doesn't mean sending your resume on a yellow background or getting creative with format. It means standing out so much as a great candidate based on what's on your resume—not the format or look of it—that no matter who else the hiring manager looks at, you remain ingrained in their memory as the candidate they're most keen on, right from the start.

Anchoring bias is a form of cognitive bias where people's decisions are influenced by the first piece of information they receive, or a particular reference point, aka an anchor. If you make a positive impression from the very beginning, before they ever even meet you, you're taking advantage of a very natural and common human behavior.

But how do you become that anchor, exactly? Well, that's what we're going to tackle together throughout this book. For now, let's walk through some other things you should know and think about before we even touch your resume.

How to compete: no more spray and pray

There are some scary anecdotes out there that seem to point to an extremely competitive job market: people who've spent over a year applying for jobs (the average is anywhere between two to six months) and people who've sent out hundreds of job applications not even to get a single interview (this Reddit post comes from someone who spent over 1.5 years, sending over 300 job applications, and still couldn't land a job).

The picture that's painted makes it seem as though no one's getting jobs—and yet, they are. So are these anecdotes coming from people who are just such terrible candidates that no one wants to hire them? Not really. They're average, probably great at some things, not so great at other things, just like me and you, just like most people.

They're telling the truth, their truth. But their truth isn't entirely accurate.

There are a lot of jobs out there. And yes, a lot (sometimes a lot a lot) of applicants per job. In fact, that number seems to be rising. In the early 2010s, the average corporate job posting attracted 120 applicants, but within a decade, that number rose to an average of 250 applicants per posting, almost double.

But if there's a job that receives 300 applications, that doesn't mean that for every 300 people, there's only one job available. Things feel more competitive because technically they are, when you've got that many more people competing for the same jobs. Except, most of them are basically copying and pasting their resumes, probably not sending cover letters, and applying to five jobs a day.

This kind of job market makes it tougher on hiring managers who need to sift through so many more applications. And when it gets tougher and noisier, it takes even more for candidates to stand out. It's a self-perpetuating cycle, and technology has kept up with the convenience it now affords.

This means that all that advice you've been told about tailoring your application? Yes, it's the right advice and it works. I know it's tempting to try to increase your odds by applying for more jobs, but it doesn't really work that way. You land in the maybe pile, at best.

So that's the first shift to make if you haven't already: it's time to stop the spray and pray tactic, also known as the shotgun approach. Rather, really think about companies you'd be proud to work for and take a targeted, tactical approach.

Put on their pants

The second fundamental shift that you should make while preparing for your job hunt is to start to think like the person on the other side of the table, or screen.

Learning to think this way is one of the most impactful things you can do for your career right now, that will also pay future dividends not just during other job hunts to come, but also in how you show up at work and how you approach doing your job, period.

I took this lesson from the world of user experience design (UX design for short), where most of the design process happens way before visuals even come in. Here, design starts with the "user", as they call it, and it's all about understanding their worldview, their values, their challenges and their needs.

A lot of time, energy and effort is spent on understanding these things through a sometimes long and laborious user research process, where among some of the tasks designers carry out include conducting interviews, studying data, talking to people and creating maps of a user's journey as they move through a product. For many people who aren't familiar with this vocation, it can be a surprise to learn that so much of this work is psychology and people-focused, but that's what design is: creating something with strategy and intent.

Now, you're not here to learn how to become a designer. But there's a reason there's been such an uptick in UX jobs in the last decade. A LinkedIn report found that UX design is among the top five in-demand job skills in 2020. Why? Because things have shifted from being a market dictated by who has the most money to reach more people, to who understands their customers and user best to better speak to and meet the needs of these people. Depth over breadth. Affinity over volume. Data over assumptions.

Your end user is whoever is looking at your resume. That could be a hiring manager, a recruiter, a CEO or business owner, or a HR person. It may also include screening tool too (which is why the oft-heard "stuff your resume with keywords from the job description" advice is given).

While each of these people plays a different role and comes to the hiring process with a different perspective, there's something they all have in common: they all want to hire the best possible person for the job. And they would ideally like to do it in as short a timeframe as possible.

When you take yourself out of your own shoes just for a little while to consider the needs and challenges of the hiring manager, you start to inhabit their perspective. When you inhabit their perspective, you start to frame things differently, focusing less on a look-at-me approach and more on understanding and then targeting their specific needs. So the very best piece of advice I can give is to think like the other person.

Let's walk through the process, using my own experience having looked at and reviewed thousands of resumes, peppered with a little bit of imagination.

X is a manager at a startup with about 100 employees. They're growing quickly and are looking to fill a role for someone who's just given their notice last week. X has been busy with work and there's no HR person, so they haven't gotten around to putting an updated job description together until now. The person leaving the role will be gone by Friday and they won't be able around to train the new hire. Plus, X is aware that it has typically taken 2-3 months from start to finish to get someone in for the role, when accounting for the amount of time they want the job posting to be up to have a big enough pool of candidates, all the way up to the time it takes to look through all applications, schedule interviews, conduct interviews (often multiple rounds to ensure the right fit), make the offer and any time between the offer and a start date so that the successful candidate can give notice at their current job.

Meanwhile, all the work that the employee will leave behind will start to put a major strain on the team, X included. It's in their best interest to hire quickly but also to hire smart so that they get the right person in the role, someone who they're hoping will stay longer than the last hire who was only here for seven months.

They've had a few people quit recently, and X has picked up on some patterns during their exit interviews. People have said that they feel overwhelmed with the amount of work they've been given. So X carries this thought in their mind as they're moving through the hiring process.

Are you already starting to get a better picture of what kinds of challenges hiring managers may be dealing with on their side? While we don't often get to see that side, with a bit of imagination and some critical thinking, you can make a few assumptions that can work heavily in your favour by studying the job description itself, the company and the industry.

Do your research

For bonus points, you can even do some advanced sleuthing by studying the social media accounts of the CEO/founder of the company or the head of the department you're applying for, information you can usually easily glean by googling "name of company" CEO or founder.

You can also search on LinkedIn. Search for the company, then click on the "Employees" section on the company's profile. You'll be able to find the name you're looking for here (unless they're not on LinkedIn), and then be able to google that to find their social media profiles. If you're lucky, they're the very-active-on-Twitter kind, sometimes even telling you exactly what they're looking for, in their words.

Things you should be on the watch for:

• their values
• their challenges
• their tone and voice

Science tells us that we're drawn to people who are similar to us, and you can use the information you find not to manipulate likability or to try to portray yourself as someone you're not, but to make a judgment for yourself about whether or not this is a person and/or company you'd like to work for, if your values align, and whether they're a "Hi Firstname" type of person or a "Dear Sir/Madam" type of person*.

*Why do I think it's important to know this kind of information? Because without it, people usually default not to their own authentic voice, but to the one they've been conditioned to believe is correct in the professional world. That conditioning is purely a product of circumstance and environment, and it may end up with you being not as high on the candidate list as someone else simply because you came across as too stuffy and formal (that's not even who you really are, it's just what you're used to), as an example. This is a way to step outside the assumptions and circumstances that may be holding you back, by doing your research.

This kind of advanced sleuthing doesn't really work quite as well for larger companies with full-on HR and recruiting departments, but it's highly effective for startups and smaller companies where the hiring manager may often be the CEO or founder. Larger companies with full-on HR departments, on the other hand, usually have much more comprehensive Careers pages and sometimes even guides to the hiring and interview process to better prepare candidates.

A very important note about a fine line

There's a very fine line between using the information you find to tailor your application vs using the information you find to manipulate and outright lie, just like there's a fine line between marketing something to people that will make their lives better vs marketing things to people that they don't need and perhaps even make their lives worse.

The way I approach it is I think of the clues I find as ways to filter and highlight what I want to, by intersecting with where all that meets my own skills, experiences, personality and values. I wouldn't ever use the information to pretend that I'm something I'm not because I'd take any sort of mismatch as a sign that the job or company isn't the right fit for me anyway.

But for example, if I find that the CEO of the small startup I'm applying for really values autonomy, and I do too, then I know that's something I can play off of in my resume and/or cover letter.

You're your own editor

So, you're a creative and a generalist. Do you ever find it challenging to figure out what to focus on? Well, when it comes to a job application, this challenge comes to the forefront. And like many things, more isn't always better.

In fact, the opposite has been found to be true: studies have shown that the fewer the choices and features and the more consistent the information, the easier it is for people to take action—this is known as the paradox of choice and it applies to all kinds of things from making a decision in a grocery store (see the famous jam test) to brand-building. (Notice how the world's most famous brands have a very clear and singular value proposition? They're not usually trying to be everything, and if for any reason, they are trying to, sub-brands are typically created to avoid confusing and overwhelming consumers.)

If you're everything, you're nothing. So be very intentional with what you decide to keep and how you present yourself. As a creative and a generalist, you have it hard because there are so many things you could include, so many possible angles, so many things you want to make sure they know. You're multi-passionate and multi-talented, but you know it doesn't come always across that way on paper; sometimes, you just come across as confusing.

Looking for clues and preparing for your job hunt by doing that extra bit of research can help you with these kinds of micro decisions that will make all the difference when your resume is in a metaphorical stack and everyone else is going the way of what's essentially keyword-stuffing their resumes. And here you are, showing up like the person they've been waiting for all along. Not because you changed any part of yourself, but because you used research to decide what part of yourself to show them.

Hiring managers are people too

Last but not least in our prep class: hiring managers are people. I find it strange actually that so many resume and cover letter guides focus on getting past auto-filters when I've hired at multiple companies, big and small, in tech and outside, and while we used automated hiring software to help keep track of candidates (75% of US companies do), we always looked at every single application that came through. Admittedly, some of them took just seconds to look at for us to decide that it wasn't going to be the right fit. I also can't claim the same for every other company out there either.

Anyway, hiring managers have probably hired before (as well as applied to jobs at some point in their lives) and they know what it's like. It's not fun to get rejected, even worse to not hear anything back at all. The earlier on they can let someone down, the easier it will be for everyone.

It does get more difficult the deeper anyone gets into the hiring process. Even when it's the final phase and there's just two people left standing, at that point, when you've met multiple people on the team and things are looking good, you still only have 50% chance of getting the job—and that's if there's only one other final candidate in the running. That's a flip of the coin determining your chances.

Nobody likes rejection, not the people being rejected and not the people doing the rejecting either. And if you're not a yes, you're probably a no because they're actively looking for reasons to narrow the candidate pool: it's less work for them and it's fewer people to reject later on, which means fewer letdowns. Even if you're a maybe, the best average resume doing everything right, you're still probably a no.

If I could make it any more clear: if you're not a hell yes, then you're a no. It's kind of like the Konmari method: if it doesn't spark joy, then what's even the point?

Speaking of Marie Kondo, tidying expert extraordinaire, there's a reason why we sorely needed a tidying guru at this moment in our history. We're all living in a noisy world with so much more information, our attention clawed away with no chance of escape except when our eyes our closed and our phones are dead.

This is what we're all dealing with.

If you can make it easier by taking a more intentional approach with what jobs you apply to and considering and really researching the job, company and industry beforehand, that in itself will save you (and your hiring manager) a lot of time and heartache in the short and long run.

Biases in the job market and hiring

Traditional job hunting advice is all about making everything as average as possible, which, as we've established by now, is the opposite of what you want to do. But there's more to it than trying to stand out just because.

Standing out isn't about being the best and most obvious choice. Sometimes it's just about levelling the playing field against everyone else who may not have to do the same work in order to stand out, people who may already have a built-in advantage. What I'm talking about is bias, racism, sexism and discrimination in the hiring process, whether or not hiring managers are conscious of it or not.

The good news is: many companies have woken up to these biases and are working on it.

The bad news is: the hiring process is one of the hardest areas to tackle, because people first need to recognize their own biases in order to actively dismantle them, unlike diversifying marketing materials, which is usually as easy as hiring more diverse models without any kind of internal work. (Thus, why using diverse models without actually improving equity, representation and inclusion internally is often referred to as performative diversity.)

One of the most oft-cited studies was one conducted by the University of Chicago and MIT in 2003, where it was found that names like Emily were 50 percent more likely to receive callbacks for interviews against candidates with names like Lakisha, even with the exact same resumes.

I've experienced this first-hand. For the earlier part of my life, I went with my given name, which isn't really "ethnic" nor is it completely "westernized", sort of a fusion of both (my parents got a bit creative). But that didn't help because it seemed to confuse people even more: my name would get mispronounced (even though it's spelled true to phonetics) and shortened (people would drop the ethnic second part, for example, calling me by a nickname that I never approved of, like calling a Richard a Dick on your first meeting).

There are also positive biases toward big names in experience and education. I was once hired for a role that I shared with someone who had gone to Yale. I looked him up before even starting the job and immediately felt a wave of imposter syndrome getting the exact same role, with probably the same pay, as someone who was a decade younger and had gone to a fancy school that I'd only come into contact with on television because I was that far removed from the Ivy League. Of course, he turned out to be smart, nice, and a great coworker, and my wave of imposter syndrome? To be honest, it never went away but I suspect it might've been because I was actually an imposter who could barely code but who did well enough on the code test to land the job, courtesy of me being really good at solving problems and well, having a great resume. Me feeling and possibly being an imposter didn't stop me from doing a really good job at my role (even though I suspect that the job was a lot harder for me than it was for him), and I was promoted within a year to the job that became a major inflection point in my career.

My point is, maybe I was lucky. It was originally meant to be one role, and he being a better coder than I was (which was what most of the job was about, teaching people how to code), probably would've gotten the job over me.

When the CEO that hired me told me later that I had the best resume he'd ever seen, that's when I knew: it was my resume that saved me and kept me in the running. My resume made up for all the qualifications, schooling and skill that I lacked. Again, I still did the job and did it very well (otherwise, they wouldn't have hired me, kept me, and then promoted me).

There's all kinds of bias, from gender to racial to even height bias (CEOs are disproportionately tall—who knew?). Up against someone who has the exact same resume, bullet points, white space, education level and all, you might not get the job not because you weren't better, but because of bias.

I hadn't originally planned to include this, and then I thought about including it all the way at the end, like a footnote. But it made its way here because I've realized how important it is. This forms a big part of why the whole concept of selling yourself is so important, not just for creative people with a generalist skillset, but especially for creative people with a generalist skillset who are also in marginalized groups.

Levelling the playing field against systemic bias, racism, sexism, agism, ableism, needs to be tackled from all angles—yes, from the people internally within a company who need to come to a reckoning with their own practices not just for moral reasons but for business value too (diverse teams have been proven to be more effective). But you can't really rely on anyone but yourself to hand you the even playing field. And you can't wait until you're over your imposter syndrome. And you can't wait until you feel ready.

If you're a woman, you're statistically less likely to feel ready than a man would: a study found that women tend to apply for jobs where they meet 100% of the criteria, whereas men apply for jobs where they only meet 60%-ish of the requirements.

I'm not a man so I can't really say what they're really thinking as it seems to me that if it's listed as a requirement, that it's, well, a requirement. I do know that I definitely relate to looking at jobs where everything looked great but oh wait, I don't know how to do this or I don't feel fully comfortable doing this, and it automatically became a pass and onto the next job I went. Until I learned about this statistic, I couldn't have known that there was an entire half of the population that didn't think the same way that I did.

Take this as a permission slip to aim a little bit higher, and not just because of your gender based on the example above. For you, it might be gender and other things. It might not even be gender at all. It could just be a belief that you're not good enough, that your path and career has already been set, that all the rejections you've already received must mean something. They don't. You just need a shift in perspective.

When you're from a no-name school with a degree that has zero relation to the job, against someone who's from an Ivy league school where it doesn't even matter what their degree was because they must be smart?

When you have an ethnic last name, against someone who doesn't?

When you're at a disadvantage because of something you were born with, that has absolutely zero relationship to how well you can do your job?

It's not fair but you have to show up better from the get-go.

Yes to companies taking responsibility and creating change from the inside out. We needed that to happen a long time ago. But it's also our own responsibility to understand the ways in which the world is sometimes working against us, not always out of ill will, but because of systemic bias (even our own).

I live in a strange city. I grew up in a neighbourhood where home prices are well over $1 million on average, not super fancy houses even, where most people living in them would not be able to afford purchasing them today. My high school boyfriend lived in a rented apartment and he slept on the floor of the living room, next to his parents who had a couch each, because they couldn't afford more. My parents inherited their home and the home I grew up in because of the last piece of remaining wealth in my family after escaping communist rule in China, where most of their belongings were burned and seized including all cultural relics of the past. I grew up without a mortgage because of that final inheritance, while my father worked a $14/hour job supporting four kids. Later on, when my mom went back to work, it still wasn't enough to avoid the life of debt that would follow. As a kid, I promised my parents I would make lots of money. I graduated from fashion school after betting on myself and taking a huge risk, convincing my parents that it was the right choice despite my mom's offhanded warnings that only rich people went to fashion school (my luck was that it was a public community college, in a suburb close to my city, so I stayed at home and paid regular Canadian college tuition). When I realized that designing clothes wasn't going to be "it" after all, I spent many years coming to terms with a future that was uncertain financially and otherwise, propped up against a carried-over impulse to do creative work.

It was an uphill battle for me in my twenties. I got lucky in many ways, but you know the saying: you have to make your own luck, or luck is where opportunity meets preparation? That's exactly what all this is.

I had to work hard in the jobs that I did get, of course, but before you can do that, before the chance is yours, you have to open the door. I had to take extra care to package myself in the right way, and when I did, that door started to open. I have a 70%+ application to interview success rate. I went from fashion to tech (and kind of back again).

That doesn't mean I always made the best decisions. Sometimes I wish that I had left certain jobs sooner and been less afraid to commit, watching other people who have moved ahead much faster than I did, making the same amount of money I do years (and now over a decade) into my career while they're just fresh out of school. Now, I change that "Sometimes I wish" to "Sometimes I had wished", because I don't anymore. It all worked out. I was able to build a creative career making more money than I imagined possible. And for me, the best part is the long path it took to get here really feels like just the beginning.

It's not easy out there. And it's not getting easier. It certainly is getting more convenient. Now, anyone can blast out a dozen resumes in a day. Overcoming bias and systemic -isms is the opposite of convenient. It requires some hard work, work that not everyone and not every company is going to do.

So what do you do?

You show them exactly what you're made of, dismantling the system from the inside out by opening your own doors and making your own luck. You won't do it on your own, but maybe if there's enough of us, we can do it together.

Your resume and cover letter are the "preparation" part of the luck equation. And by the way, luck is just a stand-in for improbable events made real, which is as good an analogy for the improbability that you'll get the job when there are 382 other applicants. But it happens, and it starts with a great resume and cover letter, also known as tools of luck and opportunity.

The principles that form the foundation of these tools are grounded in marketing, design and copywriting principles, disciplines that I've all had the privilege of working in as a creative generalist.

Rise of the machine generalist

You already know that this book wasn't written for everyone. Theoretically, the advice could apply to everyone, but it's really tailored for creative people who are currently in entry level jobs or are finding themselves in a cycle of entry level work, mostly because they don't have specific skills that lend themselves to a narrow and defined career path where the companies you've worked at, who you've worked with, and the projects you've worked on may be all you need to get your foot in the door.

When I say creative people, I don't necessarily mean artists. I actually don't mean artists at all, though I suppose that they could be. I mean people who are drawn to creating things, whether these things are objects, ideas, brands, teams, etc.

I write for them because there's so much untapped potential among creative people who aren't designated artists or artist-types like designers or musicians. They've got the ability to think outside the box, solve problems and adapt, but they're not necessarily trying to make art.

This kind of person is often hard to place and has trouble choosing a career or sticking with the things they have chosen, which sometimes means that they're stuck in entry-level, low-paying work for their entire careers. Sometimes they have many skills, but they don't usually feel that they're really all that great at any one skill in particular.

It can feel harder than ever to break out of entry level jobs, harder even if you're considering a career or industry change and aren't quite starting from scratch.

But there's something changing. Welcome to the era of the generalist.

Let's take a brief history lesson here. Industrialism, ever heard of that? It's the basis for most of our work conventions and norms today, from the number of hours (40+ per week) to the concept of coworkers (before this, most people worked with their families, which is why people used to have lots of kids. More kids = more productivity.) The industrial revolution created mass manufacturing, which became the most important work for humans for a few hundred years.

This work taught us how to work in a brand new way, creating new systems that defined our output and productivity, and how we measured success in the era of the assembly line: doing one thing, and doing one thing really well.

But, things are changing as we're now full-on facing the era of the knowledge worker and entering a new sphere of work where the biggest challenges facing businesses today are of an entirely different nature than they were one hundred, fifty, even twenty years ago.

We all learned how to do the same things over and over again, and to do them really well, and consequently, to train entire workforces and countries to specialize in one part of the proverbial assembly line.

We used to ask kids questions like "What do you want to be when you grow up?", forcing a narrative of a job and a role as the central identity of a life. (That's progress considering what we used to ask kids, particularly girls: "Who will you marry?" or as evidenced in the 1956 song performed by Doris Day, Que Sera, Sera (Whatever Will Be, Will Be): "Will I be rich? Will I be pretty?")

We may still well be asking kids this—I know I ask myself the question all the time, and I'm a full grown adult. Old habits die hard, and these are cultural habits built upon decades of conditioning.

But while the question hasn't changed (the answers have: YouTuber is one of the top most-coveted careers) the reality of work reflects a different picture than one of the singular dream career: we try on more jobs, switch careers more often, and in fact, people now take on multiple "careers" at once and it's not only socially acceptable to do so, it's practically become the norm especially at the extremes: among the ultra-privileged world of celebrity (where one can't just be an actor or a reality television star, one must be a musician, an entrepreneur, an investor, a mogul, an author, and/or a creative director preferably all at once) and the lowest-salary workers, who work multiple jobs out of necessity and who will continue to do so as cost of living continues to rise and wages are barely keeping up.

Even in the business world, out of the top companies in the world listed on the Fortune 500, 18 years is the average age. In fact, McKinsey believes that by 2027, three quarters of the companies currently on the S&P 500, a stock market index of the 500 largest U.S. publicly traded companies, will no longer be in business. So, even if you wanted to do it like boomers do and stay at one company for your entire life, unless you're looking at Nintendo est. 1889, good luck. You're probably going to outlast most companies you come across, and not just average companies by the way: these are the world's biggest companies.

What do you want to be when you grow up is an extremely outdated question, but its prevalence, despite evidence that even the world's most famous people and even the economy have moved on, sends us subconscious signals starting from an early age about what's "right" and "good".

For us non-celebrities, specialization is the much safer and socially acceptable path: "Hello my name is _ and I am a _." Being called a jack of all trades isn't usually a compliment because people naturally follow the line with: master of none.

But signs are pointing to a shift happening, where generalists are becoming much more valuable than they ever have before.

A generalist is someone who doesn't specialize in one skill. And true, they're not exceptionally amazing at any one of these skills, but when skills are widely available commodities that can be hired at any rate as our economy becomes increasingly more global, maybe skill isn't the most important thing anymore.

The rapid advancement of technology, combined with increased uncertainty, is making the most important career logic of the past counterproductive going forward. The world, to put it bluntly, has changed, but our philosophy around skills development has not. —Vikram Mansharamani, author and Harvard University lecturer

A generalist is adaptable, agile and usually has a really strong set of soft skills (more on how to really sell these later).

The irony about all of it is that many generalists are successful. In fact, many of the world's most famous and successful specialists are really generalists in disguise. Why? Mostly because of the marketing principle we learned about earlier: it's easier to be known for one specific, consistent thing than it is to be remembered for a whole bunch of things. In fact, entrepreneurs, leaders and managers tend to be generalists. They know people. They know the market. They see ahead.

A generalist is built for this new era we've entered. And their demand and value to companies is going to rise as businesses can no longer afford to operate in silos, both externally and internally. Just look around you: everything is melting into everything else. Connecting the dots is the skill of all skills.

Tech companies have caught on: the T-shaped person is someone who has general breadth with one specific area of expertise. Think of it as a bit of a twist on the "jack of all trades" archetype, a specialist/generalist hybrid that brings the best of both concepts together.

Now, if you're reading this and you have a feeling that you might be a generalist but you aren't quite sure, a sign is a sense of curiosity and along with that, an inability to pick and choose one thing.

So many of us are conditioned to think that this is a behavior to be discouraged, and in fact, I remember this being actively discouraged and frowned upon not only by my family but also peers and friends, and maybe you can relate to that too. I'm convinced this is a reason why so many generalists get stuck in entry level jobs; they try to conform to a mould but fall behind because the mould wasn't made for them. Sometimes they don't have the courage, after years of deeply embedded conditioning, to assert themselves any other way.

And by the way, you aren't going to start your career being a great "connector of dots", so don't worry so much if you think you're a generalist but not a very good one. That comes with experience.

Just like it may take 10,000 hours to become an expert at any one skill like a specialist would, being a generalist isn't a shortcut to success (in fact, because of the cultural barriers, it's kind of the opposite of a shortcut; maybe more a maze)—and it probably takes just as long to become a really valuable generalist.

That doesn't mean you don't start now. Start believing that you could be worth a lot to companies.

The bottom line is that as we look forward, generalists are very, very valuable. Most companies and businesses just don't know how to use that value, and most people don't know how to sell that value.

So what comes first, the chicken or the egg? Do you wait for companies to start clamouring for the dot-connectors among us? I say go for it and learn how to package yourself first, get your foot in the door, and we can all raise the tide of the creative future together.

The things that make a generalist's resume different than a specialist's resume? These are binary extremes with room for nuance and cross-over, but just so you have a reference point:

• Specialists focus on skills, generalists focus on outcomes
• Specialists may have an obvious career path and narrative, generalists need to craft theirs with intent and focus
• Specialists may place more emphasis on hard and technical skills, generalist may place more emphasis on soft and leadership skills

This is the end of resume and cover letter prep. Now, the real fun begins.

Basic but better: How to format your resume and cover letter

Here's my nearly foolproof format for resumes and cover letters, and all the reasons why they work.

Your resume*

There's all sorts of resumes out there, and the ones you've probably heard of are chronological vs skills-based. We're going to keep it simple and go with the format that works, which is the chronological resume, the one most people are familiar with.

I personally haven't ever seen a skills-based resume done well, not to say that it doesn't exist, just that its purpose typically is to offer an alternative for people for whom the most common resume format doesn't quite work, and that's already a subconscious cue you're sending.

You don't need that. You can go for the format that employers are most used to and make an impact. Let's go over how.

*Also known as the CV outside of North America, except that the CV is used within North America too but means something a bit different. For the sake of clarity, we're going to refer to it as the resume.

Summary

This is what I always recommend for the very top of your resume, for everyone really, but especially if you're a generalist with a diverse work background or barely any work background at all. What's at the very top is the first impression, like what's above-the-fold on a website. Most people don't do this but it's your secret weapon. When done right, this is probably the single thing that will make the most difference on your resume.

Use this space very wisely. It's like your sales pitch, a summary of everything else on your resume, written in a way that packages it even more succinctly. It's the space to put it all out there, in four lines or less. You're almost telling a story here, but instead of taking a narrative and "and then this happened" approach, you're going more in the direction of "this is who I am and why I'm great for the role".

It's like your social media bio or the text on your trading card, if you were character in a game.

Sound a bit like a cover letter? Exactly.

Many people don't actually read cover letters, and if they do, they often will read them after you've passed the first test, the resume. This space is like sneaking in the intent of a cover letter, but because it's a lot more concise and doesn't contain a lot of the necessary filler of a cover letter (the greeting, the prose, etc), it's probably even more effective.

As a writer, I figured out that this space was my big advantage. It told the story of who I was and put the pieces together in a way that made sense before they even got to my resume, so that there weren't question marks; I had already preemptively told them and made a heavy suggestion as to how they should perceive me. (See cheatsheets for examples of actual summaries I've used and some more that I've made up so you can see how powerful and impactful they can be.)

I use this space also to include a call-out to the role and the company in a way that ties into my background and skills. I'll throw in a few numbers to quantify it all (# of years if what I want to showcase is my experience). And I also make a play at my values if I can see that the company I'm applying to values those same things too.

Whoever's reading your resume could be in a state of minor cognitive dysfunction as we all are when we're busy, stressed out and burned out, and their brain is actively looking for shortcuts to making a decision in as short a timeframe as possible.

Studies show that recruiters spend an average of just 7.4 seconds on a resume—that's just 7.4 seconds to make your impression. The first time they see it, they're not going to be reading line by line. They might if you make it past their first filter and they're making final decisions of who they want to invite for a screening call. They may have hundreds of resumes to go through. They may be on a tight timeline. Looking through resumes might not even be their job. You're trying to make "yes" easy for them not by manipulating their psychology but by putting what you want them to see and know right at the front, or at the very top, in this case.

Your summary should always include a descriptor of who you are. That should align closely with the role itself. And if you're new to it, please don't put "Aspiring" in front of the role you want. Instead, follow it up with the experience and outcomes you have achieved, to augment and add value rather than to diminish.

For example, if you've had experience doing marketing tasks but haven't actually had marketing in your job title, instead of saying "Aspiring marketer...", say "Marketer with 2 years of experience in xyz achieving abc." Make your diverse background a value add.

Your summary isn't just a summary of what you have done. It's also a summary of who you are and who you're presenting yourself to this company as.

Here's some other things you can include in your summary:

• Number of years of experience
• Your top three key traits
• Types of industries and products you've worked on
• Highlights of your most significant outcomes and achievements
• A call-out to any relevant projects, interests and features

Tip: think of ways to group together related points for brevity, clarity and flow. These don't need to be full sentences so you can skip grammatically correct prose (your grammar should still be correct though, if that's not already obvious).

P.S. You do not need an objective. It should be fairly clear when applying for the job that your objective is to get the job. At this point so early on in the process, no one cares about your long-term goals yet. They're not personally invested enough to care about your objectives, they're worried about theirs. So don't waste precious space here.

Experience

The bread and butter of your resume, this is most likely going to be the bulk of it.

If you don't have a lot of experience, that's okay. Put what you can (more tips in the next chapter on how to make your experience stand out). My rule for what to leave out? If you're a recent graduate, it's okay to include work or volunteer experience during school within the last 3 years (so nothing from secondary school, for example). And if you're more than 3 years out of school, then leave it off.

Yes to freelance work.

Yes to contract work.

Yes to personal projects if your resume is scant otherwise, especially if your projects are related. Personal projects can actually work really well in your favour. If there's one seminal project under your belt that you're really proud of, include it right in your experience section, along with actual jobs. Just make sure to mention that it's a personal project: for example, after the name of the project where you would normally list the name of the company, add (Personal Work) or (Project).

If you're a serial creative with a lot of personal work under your belt (I'm talking to you, side project aficionados and side hustlers), then it's worth considering a secondary "Personal Work" or "Projects" section. Don't be shy about including this because you're not sure if it really counts as experience. Employers are not going to be deduct points for you taking liberty with what experience means. In fact, they may and more likely will admire your self-initiative. Obviously don't showcase work you aren't proud of, but otherwise, you can and should include personal work that's related in some way, either through related transferable skills or through industry. And if neither of these apply, then leave it off.

For example, if you're applying for a design role at an online pet store, only include any personal projects where you used skills that are transferable and related to the new role you're applying for, or projects that are related to pets. Don't include the blog you wrote on pop music icons from the 2000s. Do include that blog if you're applying for a role as a content writer or creator or for any role in the music or media space.

Lastly, include any media features or volunteer work. This can really help you stand out as a candidate. And that's a tip for anyone: if you're aiming to break into a new industry, any kind of toe in—whether it's something you wrote for a publication in the industry or volunteering to help run a Slack group in that space—is an advantage you should leverage.

Use this to plan ahead for any possible future career paths you'd like to explore. I use this constantly for my own career, putting one foot in front of the other by using the skills I already have to work on projects in industries that I'm actively learning about, before I even think to apply for a job in that space. I've done this successfully to get into sustainable fashion production, and I'm currently doing this to learn about and get into cryptocurrency, AR/VR and emerging technology. I call it the "stacking the bricks" method because of the way bricks are stacked not one top of the other, but in an interwoven pattern where beginnings and ends are layered to build a strong foundation.

Should you keep it all under the Experience umbrella or break it out into Experience, Personal Projects and Volunteer Work? If it's just one relevant role, sneak it in this section. If there's a couple or more, and you have the space for it (1 page if you're early career, 2 pages if you're mid-career or higher), then you can break it out.

But always use your best judgment: if you can discern from your preliminary research that this company values traits that are positively conducive to a portfolio of side projects and personal work, then separating it out makes this more obvious and clear.

It's worth repeating that you shouldn't feel compelled to include everything. I've worked on probably dozens of side projects over the last decade and only typically showcase a maximum of three (but more commonly two) depending on the role, company and industry, based on the guidelines I mentioned above.

Education

List any degrees you have as well as relevant certifications, courses and programs. Don't list everything here if there's no relevancy, the exception being those degrees. It's kind of a given that most people aren't in the same line of work as what they studied for with (only about a quarter of college graduates have a job related to their field of study), but many employers still like seeing and knowing that you have some sort of formal education.

Putting all your many certifications and continuing education courses can work against you by making people do extra work to sift through multiple lines to find what's important, and often they won't.

So choose what's most relevant. My recommendation? Three or four max. Anything more and although your intent may be to show that you're a self-learner, the cue they're going to get may work against you.

Skills

I think this is probably the toughest section of the resume, even though it's the shortest and easiest to write.

Skills are tough because it can be difficult to figure out what's a skill that's worth including here vs what's a skill that's so obvious that it'd be silly to include. For example, people used to include "Word processing" as a skill, sometimes along with their typing speed. I did include my typing speed once for a customer support role because I wanted them to know that I was ultra-efficient on chat while retaining excellent and empathetic communication skills, as evidenced by the tone and delivery of my cover letter. But would I include "Word processing"? No.

I would include any specific tools and programs mentioned in the job posting, if you know those tools and have used them before, because that's an indication for the employer that the onboarding process may be quicker because you have a head start.

Funnily enough, as much as I love soft skills, I don't usually suggest listing soft skills here and that's their paradox. As important and valuable as they actually are, they're also sometimes viewed as essential, which means that it can feel like overkill to list all your soft skills because on paper, they sound so basic (but that's the point; they're so valuable that they're practically fundamental, except that they're hard to do well).

If your goal is brevity and clarity, how do you know which soft skills are most important? What about the soft skills you don't include? Will the absence of them indicate that you don't have them at all?

This is why I actually suggest leaving soft skills off the Skills section entirely, referencing them instead through the outcomes of your work in Experience and through your overall narrative in Summary, where you do have the opportunity to highlight skills, soft and hard, that you feel you excel most in, that are most relevant to the role. We'll get to how to highlight and showcase your soft skills in a way that gets you noticed and proves that you actually have them.

So, keep it to tools, programs and technical skills that are a) directly mentioned in the job description and b) specific, relevant and common for the industry and type of role.

Example of what to include: Adobe Photoshop, Trello, Google Analytics, Canva*

Example of what not to include: Excellent communication skills, organized

*A note on technical skills: none of these is anything that takes a long time to learn. A couple of hours is all it takes to grasp the working fundamentals. In fact, a lot of the required skills and programs listed in job applications are project management tools that companies use to get work done and communicate with one another, and that's why they're listed. They're not looking for experts, just cues that candidates may be able to dive right in with minimal training.

I do recommend keyword-stuffing here, that is, looking up the skills that the job posting specifically asks for and plopping them here so that it's obvious you have them (as long as you actually have those skills).

Because the main intent here is to list skills so that I make it past the filter, I typically also include all skills on one line. It's not something that I dedicate a lot of space to. That's usually reserved for the Experience section and my achievements and outcomes per job.

Optional, depending on the company: Interests. I think this can work and is helpful if you're early career or changing careers and:

a) you have space to include this without spilling onto another page, and

b) your interests relate to the company or role in a way that isn't evidently clear anywhere else (as in, it helps connect the dots where otherwise, without this, whoever is reading your resume could be thinking, why are they even applying for this?).

So, use your discretion and when in doubt, leave it off.

And that's it. Just four parts to the effective resume.

Your cover letter (yes, you need one)

I've been an avid cover letter writer my entire life, and have always seen it as a powerful storytelling tool that of course, I was going to leverage. After all, how was I, with all my perceived disadvantages, even going to compete if I wasn't able to use what I thought I was best at to give myself a little bit of a boost? With how many words I put out as a writer, the soul I bare out on the internet, many are still surprised when they meet me to learn that I'm someone of few words, the strong and silent type ha. I was shy, someone who stumbles over my own words, who forgets my most important points and can usually be found nondescriptly scribbling down phrases in chicken scratch so that I don't forget them while speaking in video calls (which I do anyway). So I knew that I wasn't going to impress anyone in interviews if they weren't already impressed beforehand (ah, confirmation bias*).

*People have a tendency to search for, interpret and favour information that supports or confirms prior beliefs (the definition from Wikipedia).

My best chance at getting the job was pulling the strings in my favour right from the start, so that there would be a positive bias. My reserved demeanour in interviews became more of a sign of shrewd calculatedness rather than naivety and youth because of the preemptive strike of my job application—unfortunate but true, and I've lived on both sides of this, me still being me.

Because of all this, I was very surprised to learn, after I found myself on the other side of the hiring process, that many people don't write them at all. I didn't realize there was so much debate about their necessity, or lack of it.

The question about whether or not you should write a cover letter isn't will they read it? That's the wrong question.

It's about risk mitigation. Will you miss out on an opportunity because you didn't write one? Will you greatly reduce the odds in your favour? You'll never lose points because you wrote one, even if they don't read all of it, but a great cover letter definitely boosts your chances especially if you're applying for roles at smaller companies or startups where more than likely, an actual person or multiple is the first (and last) filter.

Imagine how they feel, getting page after page of resumes that all paint people as stats. Resumes are efficient but there's a point where everything starts to blur together.

Because really, what's the difference between an admin assistant at company X vs an admin assistant at company Y? If you're very lucky, you might have a big name or industry star on your resume, but not everyone does.

If your resume is your character's trading card, then a cover letter is your character's tv episode. They work together. Not everyone will watch but the people who're buying probably did.

Some of the confusion today perhaps comes from the lack of a space for cover letter attachments in some job postings, especially in online applications. And for email applications, it's often assumed that the email body text itself is a cover letter, so some employers won't actually ask for one (no one's expecting you to send a blank email but guess what: this actually happens more than you would think!). But let me ask you this: what's the signal you're sending when you attach a resume, write nothing in the email except maybe "Here's my resume, thanks", and leave it at that? Certainly not as strong of a signal as someone who writes a well-crafted, tailored email.

In applications on job portals: if there's space to attach a cover letter, plop it in there as a pdf. If not, most employers expect one in text format, inserted directly into text box on the application form (be on the watch for this, because it won't always be labelled as a "cover letter", sometimes it'll just say something like "Please tell us why you'd like to work here"—that's not a space for a one line response).

If you're applying via email, I'll say it here again: stick your cover letter directly in the body of the email and attach a pdf copy just in case the email gets forwarded or the company is filing attachments somewhere.

A great cover letter is your competitive advantage. Not everyone will read them but that doesn't matter. You don't want miss out on something because you didn't do everything you could for the people that do want to get to know you a little bit better than a stats sheet before they decide to say yes to meeting you.

My cover letter formula

I break down the cover letter into roughly three parts: one part that really showcases you, one part that really attaches you to the outcomes of the role and business, and one part that attaches you to the values of the business.

This is the formula that seems to work really well in terms of helping a cover letter stand out, presenting you not only as a strong candidate but also as the best candidate for them and one that's actually enthusiastic about the role.

I call it the triple-threat cover letter formula because the generalist in me can't resist.

I came up with it as a way to systemize writing cover letters while ensuring that each one was completely custom. I start over every cover letter from scratch, unlike the resume, where I edit down from a main document (and I highly suggest this). So I needed a way to write each one as efficiently as possible, while making sure that each one was tailored because yes, it really makes that much of a difference. People can tell when you're copying and pasting the same cover letter, even when you successfully swap out the company name and a couple keywords. (And you'd be surprised how many people are unsuccessful at updating company names.)

The reason I go for a custom cover letter every single time is inspired by my writing process. If it's not right and isn't working, it's often a better idea to start from scratch instead of trying to edit something that actually ends up taking longer to get right because you're trying to turn one thing into something else, compromising on its efficacy.

Having a set formula makes it much easier to write. I probably spend about 10-15 minutes writing a cover letter, editing included. I am a writer by trade though (as of now—that, like everything is subject to change), so that might not be necessarily your time. I bet that it'll take less time than you think though, once you understand the formula of what works.

Sticking to this formula also prevents you from accidentally over-indexing for any one of the three parts that's crucial to every single cover letter.

Talk about yourself too much and you run the risk of sounding arrogant, talk about business outcomes too much and you might come across as too intense, talk about your enthusiasm and why you're so excited about the role too much and you seem too over-eager to please. It's this exact combo in roughly equal proportion, and typically in this order, that works really well. Introduce yourself, help them see you in the role, and then seal it once you've piqued their interest by expressing your interest all over again.

Miss any one of these three and that could actually take your application from yes to maybe, with someone who has all three going from maybe to yes.

For example, I've sometimes received very strong resumes from people who were subsequently written off as over-qualified. When I thought about it more, it's not that they were necessarily over-qualified. After all, if qualifications don't matter to me as much as outcomes and potential (this isn't the case for every hiring manager, but it was for me), then how could it work against anyone? Everything on paper seemed great and sometimes they had a lot more experience, the right education, everything. But what was the deciding factor?

Most employers will always take a chance on someone who is a high-achieving individual and who they think has potential to bring them results, as long as they have the soft skills to back it up, and as long as they can afford their salary (and unless you're asking for triple what the industry standard is, true story, they probably can—most people don't care as much about a few thousand dollars difference per year between two candidates. They'll go for the best candidate, not the cheapest in most cases.)

But they're much less likely to take a chance if for any reason they think that this person is doing a blanket application, and they can't quite see or understand why this role, this company. Why? is usually the answer that's missing here, with many people thinking the cover letter isn't the place for that because the interview is.

And I don't just mean the standard "I want to work at x because..." kind of verbiage. They've heard it all.

Hiring managers but especially startup founders and business owners who are hiring themselves have egos, like the rest of us. The difference? Their egos are attached to their companies.

Look, we all know you want a job because you want money. Sure, there may be other pieces to that and which job you choose to apply for may depend on those various other things, but you want a job because you want to make money.

Yet, employers want people who can demonstrate to them in some way that they actually want to be there.

So how do you do that if you want a job because you need a job?

In order of preference, you'd only apply for jobs where:

1. You actually really love this company. You know them, you like them, you use their product.
2. You've never heard of the company before until now but after learning about them, you really resonate with what they're doing and want to be a part of it.
3. You don't care about the product and you're not ever going to be a user (common in B2B), but you really resonate with how they do things and their company culture.
4. You don't care about the company or product but this is an industry that you're really interested in, and you're looking at this job as an opportunity to learn.

And that's it. I do think it's that important to find alignment between who you are, your values and the company you're working for. I don't say it just from the employee's perspective but also from the employer's perspective.

Here's a hot tip for generalists and people who are either considering or are in the midst of a career change: I think that it's more important to work at a company that shares your values than it is to find the perfect role. If you're able to find the former (and remember to not just look at #1, but in hidden spaces where #2 may come up and to look more closely at companies who could be #3 and #4), you're more likely to be happier and more engaged at work, which can lead to all sorts of outcomes that you can't predict.

This is the exact approach I took to build my career. I never went for the role, mostly because I had no idea what job I'd be best suited for, and instead went for entry-level roles at companies I believed in so that I could get my foot in the door. And it worked.

This kind of approach is going to come in extra handy when writing your cover letter, but it also helps you cut down time overall when it comes to the job hunt process, because you're going to end up applying for fewer jobs but at companies that you're much more excited about.

No such thing as a company or job you want to work at in the entire universe? I don't believe it. With remote work now an option for many, you literally have a whole world of jobs at your fingertips.

Okay, back to the actual cover letter.

Let's go over each section in more detail (I say section, by the way, just to differentiate between the purpose and objective of each, but in reality, they flow into one another so that there isn't a discernable break in the narrative of your cover letter, other than paragraph breaks. These sections are great places to break to the next paragraph.)

Section 1: You

Who are you? And what makes you great?

Cross reference this section with your summary to highlight even further the two or three things you really want people to notice. Doing so ensures consistent messaging and a consistent story, strengthening your "package" in their eyes.

Don't pack too much in here, really think about what parts of your resume are most likely to be most interesting to this company and the role.

Section 2: You and them

This next section or paragraph is all about introducing the company and role into the context, into your "story".

That does mean that you'll have to do some research (unless it's a company you're already familiar with, and if that's the case, then that's the most ideal thing, as we just talked about.)

Section 3: Them + summary

I like to finish strong by doling out the compliments right at the very end.

There's a bit of an art to this, kind of like a dating profile. You want to seem enthusiastic but not too eager-too-please, because that could send cues of desperation. And sure, we've all been desperate for a job, for someone to give us a chance, but don't let them smell that. Poise can be detected even through writing, and that's what you want to showcase.

The ball's in your court (even if it isn't), but you're playing a game you actually want to win, not because someone dragged you into the arena.

How to strike that fine balance? Don't use words or compliments that refer to the company as "the best" or "the only", just like you wouldn't show up on a first date telling your prospective partner that they're the one, before they've even said a single word. Tell them what you genuinely appreciate about them.

The trick? What you genuinely appreciate can come from any angle (the most important thing is that it feels real to you—the more real it is, the more authentic it will come across).

Here are some ideas:

• The product
• The brand
• The culture
• The values
• Their progress (careful with this one; you don't want to come across as wanting to hitch a ride)
• The people (this one can be tricky but it was true for me when I once worked at a startup and cyber-stalked the small group of employees to see if they were people who I felt I could learn from)

There must be a reason you chose this company over all others, even if it's among a few or dozen you're applying to. Find something you actually appreciate and that will got a long way. One, maybe two sentences, is plenty enough and much more impactful than an entire over-gushingly generic love letter.

It's all a bit full circle: we're talking about how to write a better cover letter, but it's really about how to choose jobs that are more aligned with who you are, because that goes a long way too.

How to keep it organized

Write both your resume and cover letter in a word processor, cloud-based if possible so you can track changes over time and across the multiple devices you may own over the years, like Google Drive or Notion.

Really, you can use whatever you want but I prefer this versus a graphic design program like Adobe Photoshop, Illustrator or even Figma, which seems to be popular among designers but can be a hindrance because, well, they're not really designed for documents.

For Resumes:

• Keep a main resume that can apply to most jobs. Whenever you start a job hunt, make a copy of your last main resume, update based on anything new that's come up since your last update, and add the month and year to the title for easy future reference.
• If you're looking in different fields or different types of roles, take your time to create a couple of variations that start off tailored in that direction. This will save you a lot of time and effort down the line.
• When it's time to apply for a role, make a copy of your main resume to make small edits in. Then, save the edited version as a pdf.

For Cover Letters:

• Write a new cover letter from scratch for every single job you apply for.
• Keep it in a folder organized by year or by industry or role, whichever works best for the types of jobs you're applying for, year if there's not a lot of variation between the kinds of roles, industry/role if you're going the generalist route and are trying a few different things. (I don't typically look back at cover letters as I would for resumes but it's still nice to have them organized, just in case.)

Always upload your resume and cover letter as pdfs. With any other kind of format, you can't guarantee how things are going to look when they're received on the other end and you can never assume what operating system or programs people have.

I've worked in all sorts of industries and companies who had different standards for tools and while at this point, most programs can open up the most popular formats, they don't always come out looking as you might intend. The only thing that works across everything? A good old fashioned PDF.

How to make it the best-looking resume ever

Answer: you don't.

Earlier in my career, I tried to make my resume "pretty" mostly because I thought it mattered. If not for certain professions then at least for the creative industry where visuals matter. It didn't.

I spent way too much time on this. Since then, I've swapped out branded colours, my name in logo form and arguably better or worse layouts for simplicity, and my resumes that got me jobs have all been black text on white, in Times New Roman, Arial or Calibri.

I've never said yes to a candidate because their resume looked nice. Yes, even as someone who is a very visual person. And yes, even as someone who has helped to hire for visual and design roles too.

In fact, spending too much effort on a good-looking application package can sometimes even have a negative impact as it can be seen as an indication not of attention to detail but of wasted effort.

Possibly a small business owner or startup founder's worst nightmare is hiring an "artiste" who sits there all day pushing pixels and making things pretty. It's hard to manage this kind of person because they can't exactly make a justification against their work since visuals aren't the easiest to quantify in value. But they know that they'd much more prefer to hire the person who gets the right things done and adds quantifiable value to the team. (This is partly a reason why UX and product designers are paid much more than visual or graphic designers, in general.)

And if your aesthetic doesn't match up to the interviewer's for whatever reason? Theirs might not even be the same as the company and brand, especially if they're not themselves on the design, brand, or creative team (and they probably aren't). It could have the unintended effect of turning people away. Not that this is fair, but remember, have some empathy for the person on the other side. They're looking for reasons to say no to make their jobs easier as early on in the process as possible, to avoid giving false hope later on.

As much as I am a fan of Elle Woods, this is not the time and place for pink scented paper. A place I do often suggest bringing more of your personality to is your personal website and portfolio, but more on this a bit later.

The only strategic design decision that needs to be made is making sure things are aligned and indented correctly (because this is a visual cue of detail), that text is clear and whatever needs to stand out stands out. Things like white space, bullet points and emphasized text help.

Choose any font you want, but I usually stick to standard system fonts because I don't need anything else. (Yes, you can use bold and you can use underline very very sparingly, as much as it may be seen as a design faux pas—yes, really. I've heard this before in the design world. But, bold and underline was invented for a reason: to help with visual emphasis in a standard, recognizable way.) See my resume and cover letter templates for examples.

Summary? Keep it simple, clean, and don't sweat branding. The most important thing you can do visually for your resume is make sure that headings look like headings, that text is legible and that alignment and indentation is correct to help create harmony and flow, or rather prevent the disruption of it for the purpose of easy scanning.

Cover letters are even simpler, since by this time, your resume has most likely already been read and they're already at least slightly interested. You really don't have to do anything with it except keep the same fonts. In this day and age, you don't even need to put your letterhead with your address and all that at the top. Your name, email and position you're applying for is enough before you jump into hello.

Now that we've covered the basics: foundation, format and looks (basically, my version of the standard resume and cover letter advice), it's time to get into the nitty gritty of how to go from the 'maybe' pile to leapfrogging past your competition.

Advanced lessons for really serious* job-hunters

*You're not playing around when it comes to wanting a job. You want a great one, and fast.

In this section, we'll cover in detail the bits and pieces of creating not just a good resume, but one that really stands out. It's broken up into three parts:

• Thinking and communicating in metrics and outcomes
• Selling your soft skills
• Creating your story and strengthening your narrative

Together, these three skills in themselves not only dramatically improve your job application, but learning to think this way will improve your long-term job prospects and career path by helping you become a high impact player who can move between jobs, companies and industries.

How to think (and communicate) in data and outcomes

Your first lesson comes courtesy of the world of psychology, marketing and copywriting: metrics work. Ever notice the headlines on magazines and media sites? There's certainly an art to headlines that grab attention and using numbers is one of the best ways to do it. There's also an art to not making it sound sleazy, but the irony is that people will still click on the things they think are sleazy. I know, it's strange.

How it works best for you is to use numbers to quantify the work that you've done, not who you are. So you're not going to say something cheesy and weird like "I'm one of the top 3 marketers in Brooklyn and here's why" even though I bet that if you did, you'd certainly grab their attention, just not for the right reasons necessarily. (I'm certain there will be outliers though, and if you tested this on 100 people, you'll get one person at least for whom this type of language does resonate, and maybe they're also the type of person who also enters spam sweepstakes.)

I've been a copywriter and being self-taught and having written copy for many industries, I learned more than one way to write copy. It's a fascinating world.

There's one camp that really gets into psychology and uses that to "hack" their way to achieving an outcome. This is seen on lengthy sales pages, which many people look at and scoff at because they're so obviously salesy that they couldn't possibly work. And yet, they do. Some of them make millions of dollars, with nothing but text.

There's also another camp which is more brand focused, where it's less about psychology and conversion and more about words that strategically align with a brand, their voice, their messaging and their values.

And here's a secret: most copywriters who write one kind don't and can't write the other kind of copy. I've written both, a privilege that comes from being self-taught and actively putting myself in different industries with different norms. And I've tested a lot of copy over the years. (Also another point: a lot of copywriters get hired and don't actually get to see the results of their copy. So they don't actually know what works or what doesn't, just what they or their managers liked.)

Here's what I found: there's a way to write brand-focused copy that also converts. Translation? You can write in a way that isn't sleazy, that still sounds like you, and that also positions you as the most valuable candidate.

How? Your resume is definitely the place to up the ante on outcomes, metrics and achievements. If anything, think of your resume as the cover of a magazine designed to promote you and all the bullet points are things that should stand out as scannable, that get to the point quick. (The cover letter itself is maybe the editor's letter. I know, it's kind of backwards, but that's the way it works now.)

People like numbers and they're more likely to believe a statement with a specific number attached than they are to believe the same story without a number.

I've read thousands of resumes and by far, it's the very, very rare minority who actually listens to this fairly common piece of advice: quantify what you've done.

(Except in the case of people who take this too far with the bars that show your expertise level on particular skills. Please don't rate yourself. Think about it: what does rating your skills actually tell people? That you have no confidence or that you're transparent about your lack of skills? Or the opposite? There's no clearcut story here. And remember: anything that isn't clear and engaging doesn't make the cut.)

This piece of advice works so well that I actually use it a lot outside of my resume and cover letter too. When I write bios for my website or copy for clients, I search for metrics, and I find them in all sorts of ways, in all kinds of places.

In fact, I just did it two paragraphs ago when I said that I've read thousands of resumes. I could've said that I've read a lot, and a lot could mean more than thousands. It could mean millions, for all you know, if I were some sort of super-human android. But I'm not and the fact that I put down "thousands of resumes" over "lots of" is a strategic choice that works to build my credibility.

And notice that it didn't even have to be a specific number to work. Specific numbers are really great to have, but not many people have them. And like, it'd be kind of weird if I had some sort of spreadsheet going from years ago where I was adding every single resume that I've ever looked at, just for this purpose. So I always go for a known truth (a range) than a made-up number.

Because I know you've probably heard this before but still probably aren't doing it, this section won't be like this: just do it. But it's okay if you haven't heard this before, especially if you're new to your career. You're ahead of the game and learning how to quantify your outcomes will build your career faster and further.

There are three places where metrics matter:

1. In your resume, in the Experience section (this should almost be entirely quantifiable metrics)
2. In your resume, in the Summary section (pull up metrics that summarize your qualifications as a whole. This is where you can group things like cumulative years of experience or total number of clients, as examples.)
3. In your cover letter, in the You section (highlight one or two most impressive and relevant metrics and outcomes)

Let's go over the Experience section, since this is where it all starts. The other two are much easier to do, once you get over this hump.

The bullet points below each of your jobs in this section are the most important part of your resume, especially for generalists. Well, that may be arguable. The resume format that I go with includes only the things that are important, but I'd say Experience is what most employers focus on and is at least the biggest chunk of your resume.

Here, you can get a bit creative with presentation. I don't mean how things look but carefully editing and refining the words you choose and the skills and accomplishments you decide to showcase. You get to decide what matters.

First and foremost, this is not the place to list out all your job duties. Instead, reframe this as a section to list out your job outcomes and accomplishments.

Most people actually don't know this, and if you ask employers and hiring managers, they might not even themselves be able to articulate it, because it's often a subconscious thing: they aren't really looking for a complete list of your job duties, especially if you're starting over or just getting started in your career.

The subconscious expectation that they have is that if you're applying for the job, you think you can do the job. They're not looking for essentially a reiteration of the job duties and description, which is what you might assume if you've heard the advice that you want to insert keywords from the job description because that's very, very common advice.

This is good news for you if you're a generalist, a career changer or early in your career without a lot of relevant job experience, because the tasks that you've actually done may not even be the same job tasks that are relevant to the job you're applying for (more on transferable, soft skills in the next section.)

What they're actually looking for are clues that you're a high-impact person. A high-impact person doesn't just do tasks, they create outcomes. Instead of thinking, what can this person do, they're looking for answers to the question: what results can they get?

Some employers know this, but not all. Many think they want to see an exact replica of the job description in the form of your resume with your name on top. But the reason this doesn't work is because that's the vantage point that everyone else is coming in with. Everyone else is also copying and pasting lines from the job description into their resume, and changing a few words to "customize" their resume.

Thank you, but next.

They're not necessarily even looking for the same results, just that you're capable of getting them. They're looking for the pattern.

Listing outcomes also creates a cue for what kind of a person you are: someone who is results-oriented in practice not just in theory (in theory, that would be the person who says "results-oriented" because that's a keyword but doesn't show proof of it).

Why doesn't listing your job duties and tasks work as well as you think it should? Well, anyone can be taught to do tasks. And let's say you've never actually done the task before, you can't list it on your resume because that would be lying, but that doesn't necessarily mean that you can't do it, right? That doesn't mean that you can't do it better, even, than someone who's done it before just because they fell into the right circumstances.

I've gotten jobs where I've beat out other candidates who met the "requirements" where I didn't, because I had proof of a results-oriented and outcome-driven approach. On top of that, I fast-tracked into a director role within a year of starting in an entry-level one because I had proof of a strategic approach, which was firstly obvious in my resume and cover letter, and of course carried over when I was actually in the role.

If you're new to your career, then you may not have a "strategic approach" quite yet, but all this that you're learning right now is the beginning of that. Strategy just means intentional planning to achieve outcomes, and in this case, we're working backward to achieve the outcome of getting you the job.

In copywriting, I liken this to the difference between listing benefits vs features. Benefits are what people really get, features are the line items that people only tend to cross-check and skim at the very end to make sure that the specs are what they want. But the benefits are where the "sale" takes place.

Here are examples of what most people's bullet points look like:

• Responsible for organizing events and panels
• Assisted customers in store
• Identify and contact affiliates

And here are examples of what you should be aiming for instead:

• Wrote subject lines for emails with open rates 8% above industry average
• Mentored thousands of clients on topics related to conversion marketing, UX, and SEO
• Organized and produced over 8 sold-out industry panels

Again, the lazy (and standard) way is to take some of the keywords from the job description and to incorporate them into your resume and cover letter. That's better than nothing. But the next step up and what will really get you results is to think about how you can show them that you can do these things, like the adage, show don't tell. (Which is not entirely accurate since we're telling them something still, but you get what I mean.)

You might discern that the company you're applying to is a startup and are really looking for someone who's autonomous. Basic resume advice is to mention "autonomous" a couple times so that the resume filter picks up on those words and adds you to the yes pile.

That's largely a myth and isn't typically what happens, at least in any of the jobs I've hired for. (I can't say that it doesn't happen at all. I'm sure it does. But it happens probably less you might assume). And again, if everyone else* is doing the same thing, is it really going to work?

*That's an exaggeration; I'd estimate that for most roles, it's less than half who will actually go through the effort to do this very basic task.

The more effective way to do this is to show that you're autonomous by telling them about something that actually proves it.

One thing to keep in mind here though is that no matter what the job description says they want, what everyone really wants is someone who's really great at what they do and is a team player. Impact and your ability to work well with others is 80% of it and that matters a lot. So when in doubt, or when on a time crunch, going through this process of applying data and outcomes in a more general way is still way better than doing nothing.

Okay, so outcomes not job duties. But what do you say and what do you leave out?

That depends on your level of experience and the number of pages. If you're junior and less than 3 years into your career, keep it all to 1 page, no exceptions. If you're mid-level or higher, keep it to 2 pages, no exceptions.

That main resume I mentioned earlier? It's a huge time-saver, since you'll already have everything laid out in front you. When it's time to apply for a specific job, you can then go through and start editing by process of elimination to fit the context of this specific role and company.

Based on the page limit, I eliminate as much as I need to so that everything fits while still maintaining a legible 11 or 12 font size. Shuffle the order of the bullet points too, so that the most relevant and impactful outcomes are listed top to bottom, then eliminate anything that's extraneous.

This isn't the place to try to fit it all in. Your page limit is a built-in mark for figuring out what information to prioritize and what the upper limit of information most people can easily digest and skim before they feel overwhelmed.

Tip: if there's just one single line that you want to keep and you really tried your best to eliminate the non-essential information, just adjust the margins ever so slightly so that there's not really a visible difference, and your hanging line disappears.

Brainstorming for these bullet points

Here are some impact and outcome-related points to help you form these bullet points:

• Number of customers, clients, projects, events, partnerships, etc.
• Growth in revenue or market share
• Number of media mentions
• Growth in headcount (can seem very impressive for any role with an operational context)
• Marketing metrics like email open rates, click rates, social media following
• Customer happiness ratings
• More abstract impact outcomes like implementing a new office recycling program (bet you can think of a way to quantify things like this too: what was the adoption rate? the timeline from concept to delivery?)

Start this habit now

What makes this whole entire process easier? A win list.

You can call it whatever you want, and put it wherever you want (ideally, also something cloud or browser based so you never lose it), but basically this is a folder, document or notebook that contains every single win that you've had at work or in work-related scenarios.

Honestly, you could have one for other things too, and I highly recommend it, but since we're talking about work, that's what we'll focus on.

Includes:

• any data that you have from positive performance reviews
• things your clients, customers, coworkers and managers have said about you (you may not be able to use this in your resume or cover letter—I actually did once and it worked—but it's still a win)
• positive feedback on outcomes you've achieved
• any metrics (sometimes you'll have to go look for these yourself if you've worked in a small business, as long as you have permission and access to do so)

Keep your eye on and note down metrics as you achieve them in your role (and even if you don't, keep your eye on any metrics anyway, including general ones that may not be related to your specific role).

When you're exiting a company, there's so much going on when it comes to winding down tasks and sometimes helping to train your replacement that it's hard to remember this to do this.

You may not be able to use the wins in their exact form, but look at this document whenever you're updating your resume and you may find some long forgotten outcomes and achievements that are suddenly relevant again.

A note about relativity

Any number is better than nothing, especially when considering relativity, and a range when you have it is also better than nothing.

That's because any metric and outcome can be leveraged as a positive thing.

If you've worked with many clients and companies but didn't go deep into metrics, talk about volume and breadth (ie "worked with dozens of clients in x, y, z industries" is better than "worked with clients to write copy").

If you haven't worked with a lot of companies or have a lot of experience, but you've worked on a project where you had a lot of control and autonomy, talk about your impact because hint: smaller companies, by nature of their smallness, typically have much more impressive metrics (ie "Achieved 30% email open rates" vs "Wrote emails that had high open rates").

You can leverage working at a larger company with volume-based metrics, which will seem impressive when applying to a role at a smaller company or startup later on. The reverse can work effectively too: you can leverage the breadth and impact you have working at a smaller company, which can seem impressive when applying to a role and a larger company later on.

It's all about how you package it.

How to sell your soft skills

No technical skills? No worries.

Soft skills are your power play. You may have heard attempts to rebrand these as "power skills" or "foundational skills" because of connotations around the word soft. Personally, I use the word soft because I think soft is a powerful thing and I don't think we should have to cater to binary standards of what power means. Just because something is soft doesn't mean it's not impactful, and we're about to prove it.

Here's what I mean by soft skills being your power play: technical skills are often the baseline for certain jobs. If you're a developer, for example, you need to know the programming language the company you're applying for is coding in. But having that technical skill puts you in a pool along with every other person who meets that baseline criteria. You think that you have the perfect experience, but so does almost everyone else. And even when you do have the perfect experience (in your opinion), you may still not even get through the front door against someone else for whatever reason.

For jobs that don't actually require any technical skills? It's very, very hard to understand what even qualifies you in the first place, other than perhaps what you've already done. As you may have seen by now, I don't like that approach because what you've already done is in no way an indication of what you can do, and what you might even be able to do better than someone else who has done it before.

I've learned this lesson over and over again, starting out in many jobs inexperienced but leap-frogging after a little bit of mentorship, observation and self-taught prowess. (I became Head of Content with no prior jobs in content. I also became a Social Care Lead at the fastest growing company in Canada with no prior experience in leadership or management, or "social care", for that matter. They could've chalked it up to "talent", but was I more "talented" or even skilled? No. Could I have become more talented and skilled over time? Yes, probably.) And I now apply that to lens on the other side of the table.

Your safest bet isn't to rely on your technical skills or experience but to go all the way in selling yourself, and that means understanding the full scope of what it means to be a good hire and a great employee. Hello, soft skills.

As if this wasn't a big enough clue: all the best and most effective leaders aren't necessarily the most technically adept—in fact, a common mistake when promoting people is promoting people who were the best at the job, who may not be the best managers. The best leaders, literally the people helming companies, at the top of the corporate food chain, are extremely soft skill proficient. In fact, various studies consistently show that successful and effective leaders, not just in theory but in practice, all have strong soft skills in common, not a single technical skill in sight.

So soft skills count for a lot, but it's a bit of a tough dance because some of them seem so, well, basic. You don't really want a resume full of basic keywords that make you sound like a common denominator human, like the "fast learner" who "thrives under pressure" that surely everyone else is too. You want to stand out. Thankfully, there's a way to do it with soft skills.

Here are three tips for selling your soft skills:

Polish your writing.

Okay, okay. So this is advice you've heard before. But I want to dive a bit deeper because as prevalent as the advice is, it's still missed a lot.

Resumes and cover letters give good written communicators an inherent advantage. Until video resumes and cover letters become standard (which they might, you never know), you can sell yourself better just by writing better.

This means the standard things like making sure you don't have any typos, that you're using the same tense across all your verbs, that you're conscious of your audience and what their preferred tone may be, whether ultra professional or a bit more approachable.

This doesn't mean using fancier words. In fact, often times it means the opposite. Articulate and well-spoken writing often uses simpler language in a way that demonstrates a stronger command of words and meaning and their meaning. If you don't consider yourself a strong writer, I recommend outlining your cover letter, then recording yourself as if you were talking to someone. Transcribe that, then polish it so that it's one step up more professional while still sounding like you.

If you don't feel confident in your writing or proofreading skills, I highly suggest having a friend who you know is a great written communicator take a look through your resume and cover letter. If not, you can hire someone on Upwork or Fiverr for a small fee. You never know what they'll spot. I'm a professional writer by trade and I've never once turned in an article that was perfect and ready to publish (which is why it takes me 2-3x as long to publish something if I'm editing it myself.)

Don't just use the keyword; show them the outcome.

I have to repeat it here because it bears repeating, just to drive in the point some more. Don't just tell them that you're "autonomous" or a "team player". Remember, most people are doing this already.

What did you actually do that demonstrated that?

For example, if autonomous is what they're looking for, you might want to prioritize independent projects you've worked on or saying things like "Managed 5-8 clients at a time independently".

If a "team player" is what they're looking for (who isn't?), you'll want to mention any projects where you worked with others. Where you normally might list out just your specific role in the outcome or achievement, instead you might say something like "Worked with a cross-functional team of project managers, developers and designers to x".

You might not think that that first part is the part that matters because it's not what you did, but that's what employers are looking for.

Quantify (and qualify) your people skills.

One time I applied for a job and after I got it, I was immediately put onto writing articles about soft skills even though that wasn't in the job description at all. At first, I wasn't sure where the idea even came from; I certainly didn't pitch it. I didn't talk about soft skills in my application package or in my interview, but clearly, they thought that I was the one.

Later on, I realized that I did what I'm telling you now to do: you don't demonstrate that you have soft skills by saying you do, or even listing the keywords in your Skills section (I actually don't recommend listing soft skills here). And showing them the outcome is a great start but to really emphasize it, you need to leverage the power of association that soft skills have with people skills, because that's what most of them are.

That means that anywhere and any way that you can quantify and qualify the work that you've done with people that proves any sort of success in that arena, is a really really good thing to include.

Examples: were you a manager? How many people did you manage? Did you ever have customer-facing roles? Did you have any significant volume or outcomes in these roles? Did you ever freelance and have clients on your own? Did you manage multiple people and projects?

These are all basic questions that answer one part of the equation, helping you quantify your people-related roles. But don't stop there. Something that many people miss is telling the story of your perspective, your results, your approach, and that can say a lot more about your skills than the numbers even though numbers help to add weight. That's what I'm referring to when I talk about qualifying your people skills.

So instead of just saying "Managed 5-6 reports", you could say "Managed 5-6 reports in a fast-changing environment while maintaining a strong focus on professional development." The former makes you sound like every other manager. The latter shows them what you value.

Speaking of storytelling, that's a perfect segue into the last but not least important lesson for creating a standout job application package.

The story you tell paints a picture of who you are

Let's face it: a job application is pretty dry by nature. But people are drawn to stories. So what's the right balance to strike?

Specificity doesn't just come through in numbers, it also comes through in stories. A story makes you memorable. I don't really mean "Once upon a time" or even telling your life story in your cover letter, although that may be a question you'll get once you move to the interview process.

Before I start customizing my resume for the job I'm applying for, I always think about the picture I'm trying to paint of who I am, in the way that best suits the role.

Specialists don't often have this liberty, but because I've worked in all sorts of roles in various industries, I can pick and choose. And in fact, I kind of have to know what to include and what to exclude to avoid confusing the hiring manager and get written off as someone who has no clear direction. (That may well be true, but it didn't mean that I was a poor employee. I've always been a great one, no matter where I was with my own personal goals and clarity of career path.)

For example, if the role I'm applying for is a design role but I don't have any experience working as a designer, I'll consider what my advantage and point of leverage is. In my case, it would be that I've worked on creative teams with designers, that I think strategically like a designer, and that I'm ultra-organized and can work on multiple projects at once.

If I'm applying for a role in content, I might draw from some of the same experiences and skills, but I might hone in more on any roles or projects where writing was a big part, tailoring the bullet points in my resume, the outcomes, my summary and my cover letter to tell a different story based on the exact same experiences. I might include the copywriting I did for the social media account, or the forum posts I wrote while working in a customer support role.

If it's social media, well, I've done that a lot but it wasn't ever my job title, but I can highlight things that I wouldn't have highlighted otherwise, like engagement and follower count, the campaigns that I created and produced, the influencer programs that I set up and the programs and tools that I used for social media scheduling that I would've left off my resume if I was applying for anything else.

Similarly, if I'm applying for a customer support role, I might focus more on all my operational experience, my customer-facing experience, and use the points that I would've highlighted in the other stories about myself more as the backdrop to showcase my cross-functional breadth and that I understand the entire product development process and how important empathy and both quantitative and qualitative feedback is to creating better products.

See how you can turn "adaptability" into a story that's more outcome-focused?

You might not be able to pull on these specific things, but I encourage you to stop listening to the story about yourself that says you don't know what you're doing or that you need to choose. Instead, you're creating your own story and you have options to choose from. And the option you choose right now isn't a limitation of your options down the line.

Take some time, maybe sit down with a cup of your beverage of choice, and really think about where you're at now and the paths you'd like to try. What are the outcomes, skills, jobs and experiences that specifically relate to those specific paths? What are the outcomes, skills, jobs and experiences that specific employers and industries care about?

The story I end up choosing is often rooted in where my skills and experiences meet the role and what I believe to be the state of mind or perception of the company or industry I'm interviewing for. Take some time to think about what challenges they're dealing with, where they're heading and the opportunities that await, and how you fit into that picture.

Do some research if you need to. If you want to get into tech, there's a lot more focus on growth and data than there is at a creative agency, where the focus is more on balancing projects and executing quickly. Where you want to work influences the story you should tell about yourself.

I've landed a job where I was actually lamenting my flaky work experience, until my hiring manager told me I stood out because I had such a diverse work background and she was specifically looking for a new perspective, as well as for someone who was adaptable and could integrate quickly into a fast-paced environment. Note again that I didn't use the word adaptable or fast-paced environment (show me a job that asks for someone who thrives in slow-paced environments), but she was able to discern these things from the story and outcomes in my resume.

Any story, no matter how diverse and how haphazard when laid out all at once, can make sense in the right context when you use some storytelling and marketing principles to pull it all together.

You don't need to show them everything; highlight skills at the intersection of what you're best at and what the role requires.

Finally, here's one thing that I recommend to creatives and generalists especially who've worked for smaller companies and startups where the name of the company isn't easily recognizable. Like I mentioned before, big names can help and up against someone with them, the other person automatically has an advantage.

It's the same reason you might see people name-drop media mentions in their bios or on their websites. I do this too; it works. (But I also knew how to tell the right story earlier on in my career when I hadn't worked for any famous names. See "I have written copy for dozens of businesses from startups to fashion designers who've been featured in xyz" vs what I'm now able to use today, which includes some of that breadth because that's what I still want to showcase, along with some very strategic name-dropping of actual clients who are well-recognized.)

It's a form of social proof to have worked at a well-known company. But there's a way to build credibility even with smaller companies who aren't recognized.

In your resume, below each role that you've had and above the bullet points for that role, consider writing a very brief 1-line max summary of the company.

Just like everything else you've learned so far, instead of copying and pasting their company description, think about what would be most relevant to the employer, as well as quantifying any outcomes and using social proof where you can.

As an example, if the company you're applying for has identified that one of their values is environmental responsibility and you've worked at a company that shared that same value, then it's worth bringing that up and highlighting it: CompanyX is an environmental consulting firm with clients in the forestry and urban planning sector. That actually sets your story up much better listing CompanyX and your bullet points with no context as to what the company actually does or how that plays into your story or the job you're applying for.

You can tweak this slightly depending on the job too. In one version of your resume, it might make more sense to mention the industry if it's related and in another, it might be more relevant to mention any awards or accolades.

Their social proof is indirectly your social proof.

Do you go in-depth into each company on your cover letter? No, unless you think there's one company that really might be worth pointing out.

I don't see this being done often, and I don't always do this if I don't have the space for it, but I think it can work especially well if you've had experience working for a company that's in the same industry or field as the job you're applying for, or if you're applying for remote jobs where more than likely hiring managers have not heard of the companies you've worked for because they were local, or if you've only ever worked at small businesses.

An alternate option is to tell a one-line story of something you want to highlight about your role in relation to the job in a way that's not quite relevant to any specific outcome. For example, if you were the first hired designer at a startup, that can be a highly valuable point for jobs at other startups where they're looking for someone who's autonomous and can operate as the solo designer. In that case, you could use the same space for something like "I was the first hired designer working on xyz" to really call that out.

So, tell the story not just of yourself through your cover letter and which bullet points you decide to keep on your resume, but also of story of the companies you've already worked at.

Future-proofing your career

So far, we've talked about how to present yourself. Now, we're going to talk about what you can actually do to improve your career prospects for the long term as a creative generalist. This is a bit of a (very important) bonus, the cherry on top of this whole "packaging yourself" thing. Why? Because learning to communicate and market yourself better can take you very far with very little extra effort, but sometimes to make a bigger or a longer term change, you need to reach further and go beyond. Sometimes you need to actually take action.

We'll start with tips for your job hunt beyond the resume and cover letter—in other words, what to do when you've optimized your resume to perfection and still aren't where you'd like to be, or what to do when you've optimized your resume and are looking to keep going in future-proofing your career.

Then, we'll finish with some parting words and a summary of some broad trends impacting work and jobs, so you're not just doing but also thinking about what's next for you.

From you to the world and beyond, all of that matters and that's what this final section is all about: looking beyond the metaphorical piece of paper and at all the other pieces.

Make a play in the startup world

I see a lot of people who've made their careers by taking a chance on a startup. It's smart. After all, startups that aren't that well-known don't have a lot of leverage because people are always looking to hot brands and big names, if not for the clout then at least for the salaries.

But choose the right startup and you have an in, not just into a new industry but into the entire world of fast-growth and high-stakes tech. It can change the entire trajectory of your career and your earning potential, in one of two ways: the salary and the skills and outcomes you'll be able to achieve on a smaller, less structured team. Both these things have the potential to make a huge impact on you, your career, and your life.

I once had a job in tech where my coworker asked what salary I was making. I had never been asked this before, but when I told them, their jaw dropped open because they thought that I was making "way more". I didn't tell them that what they considered to be low was in fact the highest salary I've ever made by a long haul, nor did I tell them that their salary was about twice what I was making in the job I had previously (I was senior to them), nor did I tell them that some of the people who I helped hire, who were just starting their careers, were making the same salary I was making just a few months earlier.

Sometimes I play a futile comparison game when I look at people five, ten years younger than me who got into tech much earlier, making even more than the highest salary I've ever made.

I point all of this out to say that I'm nowhere near the high end of tech salaries, and yet, I can feel the difference this money has made on my life. Getting into tech and startups changed my career and my earning potential, something I'm sure that I'll continue to feel the effects of years from now as momentum compounds over time.

Now that I work for myself, I make even more than that highest salary, something that honestly felt worlds away just a few years ago. Once you make the leap, you'll find it easier to continue to leap. Once you get out of the zone of entry-level work and entry-level pay, you'll see a whole other world open up to you.

And I wish more people knew this.

I wish more people weren't so afraid of leaving comfortable jobs, where they like the work and their coworkers, to try something new. I've tried to convince peers that I know who are still doing entry-level work at 30 to try tech, but it doesn't always work. Their biggest hurdle? They don't really see themselves in that world. They think it's all engineers and "really smart people".

They think that I got lucky because I'm "really smart people" too. I did get lucky, but I also saw opportunity, worked hard, and kept going. And when I got there, I realized that the "really smart people" aren't really that smart after all. Not to discredit anyone, but what's smart is sometimes just one form of intelligence, or it's privilege and a lifetime of insulation in one specific field which inevitably over time comes off as expertise, or it's sometimes even just charisma and confidence and well, being a man.

I love this quote from Michelle Obama:

"I have been at every powerful table you can think of...they are not that smart."

There's not necessarily a correlation between ability and salary, value and salary, anything really. It's just perceived value and right now, a lot of people are placing bets and making money on technology products and companies.

Tech is sometimes painted as a field for geeks or nerds (geeks and nerds that get paid multiple six figures and who now practically run the world with their billion dollar companies), but the big secret is that the field of tech is actually very broad. Technology, if you haven't noticed, now touches basically every industry. Technology isn't really a field in itself. And yet, there's popular discourse around the whole "get into tech" thing. What people really mean by that is debatable now.

Sometimes they mean "big tech", as in the Facebooks, Amazons, Netflixes of the world. But all of those? They're not just "tech". Facebook is a communication platform, Amazon is worldwide distribution, Netflix is a media company.

(There's an episode in the Amazon series based on the Modern Love column from the New York Times, where a man introduces himself to a woman on a train as working in tech. When she probes further because she doesn't understand what "working in tech" means, she decides that he works in advertising.)

You can argue and express dissent over the major salary discrepancies between people who work in tech and people who don't. Is it fair? No. But we live in a capitalist world and technology enables scale and growth. Scale and growth mean potential. Potential means more people are betting on technology companies, which is why pay is so much higher.

We're full force transitioning to the knowledge worker economy away from the industrial age and it's not a question of will you work in tech or will you not? "Tech" is everywhere.

The good news is technology companies need all kinds of people right now. There are plenty of non-technical roles available—and not just that they're available, but that they're fast becoming just as important as technical roles. Roles like UX design and community management are experiencing high growth and demand because tech companies are moving on from engineering-centric cultures to a people-focused ones. And sure, these roles involve technical skills, but those technical skills can be easily learned.

In fact, the non-technical soft skills we talked about earlier? They've become the differentiation factor for technical roles too. And of course: with the rise and adoption of a global economy and remote work, what's stopping every company from hiring cheaper talent from lower cost-of-living locations? Soft skills and great communication.

Startups are a special breed of tech companies. There's actually not a standard definition of them, but for clarity's sake, they're new, have high growth potential, and they involve some sort of risk and some kind of bet.

They are typically started with a goal to grow fast and get big. You don't call a local mom and pop store a startup because they're not necessarily looking for big growth. You don't call a lifestyle business a startup because the central goal of that kind of company is to sustain a certain level of income to support a specific lifestyle. Startups are often funded by outside investors (see: the world of venture capital and the billions pumped into new companies every year) but they can also be self-funded and bootstrapped too.

For example, a local nail salon usually isn't considered a startup because it doesn't have the high growth potential technology investors are looking for, whereas an app that allows people to book nail appointments in a marketplace would be because the hook for high growth is that the market could be as big as all the nail salons in the world, which is a pretty big market and a really big bet.

I'd be doing you a disservice if I didn't tell you to consider looking here, in this world of companies that most people don't know about (and to be fair, that most people don't care about in the company of overinflated egos and people who think their productivity apps are going to "change the world"). This is where opportunity lies (by "this" I don't necessarily mean the million+ productivity apps; there are all kinds of problems that still need solving).

It's not because they pay the most (compared to big tech salaries) nor because they offer stability (they don't, many startups fail: 90% of all startups fail according to Startup Genome and the stamps of investors doesn't help that much either with 75% of venture-backed startups failing according to Shikhar Ghosh, professor at Harvard Business School)—but because they're eagerly looking for great talent: smart people, people who are adaptable, agile, creative, and sometimes even downright scrappy (a word you might see on startup job descriptions that you're unlikely to see anywhere else).

You might not necessarily stay in a startup long, but you will grow and learn a lot. You'll often have to jump and and "just do it" and be able to add a lot to your resume when it comes to outcomes achieved, in a short period of time.

This is huge for creative generalists. This is huge for anyone stuck in a cycle of entry level roles in areas like administrative assistance or retail customer service, jobs that will rarely ever pay higher because the perception of the value of these roles is low. (Who knows what'll happen in a few decades when everyone is a knowledge worker—maybe retail staff of the future, whatever that looks like, will become highly paid and highly sought after.)

If you don't have a lot of work experience, customer support (this is where I started) and community management are entry-level adjacent roles that you can find as a non-technical creative. (Would you believe that you can make the same salary working in customer support as you could as a pharmacist? Obviously this isn't all customer support jobs, but it's more than you think.)

Remember what we talked about before: choose product, company, values and industry over roles. I'll always suggest this path for creative generalists because I find that we tend to get bored and disengaged when we're working on things we don't really care about. And the experience you get speaking to customers as an early hire is going to give you a huge advantage and leverage point that you can use to either expand deeper into this career or transition into something else later on, like I did.

I was about five years into my own career when I made my own leap into tech, in a customer support role. I remember joining my team and introducing myself and immediately people told me that I was overqualified. They didn't know that sure, I may have been but this entry-level role still paid more than what I had made in all the other jobs I've had before, none of which came with benefits.

After a year of getting over my usual introverted tendencies and excelling in a way I didn't think was possible (I had always preferred to be behind the scenes and not frontlines), I moved into a customer support-adjacent role that blended communications, crisis management and community management, and then a few months later, I moved into leadership. These skills all helped me stand out for the next job that I took, where I was promoted into a content role (my first). And that all happened in about three years. In the meantime, my salary quadrupled.

Here's a caveat: customer support and community management isn't necessarily easy to do (and in fact that's a big misconception about them), but since them perception of them sometimes can be, the bar for experience is often lower if you can prove your people skills—and you should be able to, now that you have the tools to do so.

If you have some work experience, you might also be looking at roles like project management (the underrated true hero of tech companies and a natural choice for anyone who's worked in operations, account management or non-tech project management), UX design (a solid choice for psych grads or anyone who's worked with people since the focus is literally on people), content (after all, "content is king"* today and this is a highly flexible, in-demand career path), or marketing (there's actually fewer straight-up "marketing" roles now, and they seem to be divided between content and analytics but you may luck upon a generalist marketing role as the first hire at an early stage startup and get to try a lot of different things while making an impact). If you have experience in sales or account management, depending on the company (common in B2B startups), there are also plenty of roles that are adjacent to this.

*You wouldn't know it based on the typically low pay in the world of journalism. Many displaced former journalists and writers who tried to hack in the world of media, either print or digital, have moved into content roles in tech. Much less demanding generally and it pays more. (Not to mention, there's a bit of a content renaissance happening now after years of content on the internet being driven by search engines. See: rise of the Chief Content Officer role.)

All these roles, by the way, are also great follow-ups to working in customer support and community management; which is to say, you don't need to solidify your long-term career goals. If there's an opportunity with a company you align with, take it.

You can make huge strides in your career by choosing to look outside the box and into the world of startups.

Here's some places to look for startup jobs:

• LinkedIn: you can enter parameters of what you're looking for and a few keywords and get automated alerts sent to you whenever new jobs come up. You can also set alerts for new jobs that come up at companies you're interested in.
• AngelList: Basically a job site specifically for startups
• We Work Remotely: A job site for remote jobs
• Remote OK: Another job site focused on remote jobs
• ProductHunt: They do have a Jobs section but it's a bit scant. I do find this to be a good place to keep your pulse on new products coming out (there's an upvoting system with a daily refreshed list), so that you can find companies to keep your eye on.
• Speaking of keeping your eye on companies, here's my favourite: following startups you admire. I did this and it worked for me. I keep my eyes open for companies that I think are doing really cool things, and then I follow them on social, sign up for their email lists, and check out their careers pages occasionally.

Bonus: many of these jobs are remote too and you'll more than likely expand your network by working with people who live all around the world, gaining new perspectives and learning a lot more about a lot more. It's an intellectual goldmine for creatives and generalists.

Work on personal projects

I 100% think that personal projects help candidates stand out.

But they don't just do that. Personal projects help you grow your skills, develop new ones, demonstrate what you value, and act as a signal of the kind of work you'd like to do.

I take this from one of the most valuable pieces of portfolio advice I ever took to heart, back when my work was visually-driven. Don't show everything. Show what you're most proud of and show the work that you want to be hired for. (Similar to how I approach resumes: show the story you want to show, not every single detail. Don't confuse people.)

I've been working on side projects since I was a kid, and I probably have dozens under my belt at this point. Some of them made money, most of them didn't. But even the ones that didn't helped me learn new skills or created outcomes that are worth noting (like press mentions or metrics that I was able to achieve). I never include all of them in my resume. Depending on what the role and company is, I might include one or two.

Most recently what I've started to do though, is to include all my side projects under an umbrella that I refer to as an independent project or content studio. So if you're someone who works on a lot of creative things, that might be something you want to consider, as it helps create a more cohesive story, tightening up your resume while still leaving space for any outcomes achieved. It doesn't have to be an official business entity for it to count as experience.

I love personal and creative projects. I love them for myself to preserve and cultivate my creativity. But I also love them on job application packages, not necessarily as the main thing, but as a standout side dish. You're helping someone else take a smaller leap from where you would've been without that project to where you are with it. You're removing the cognitive barrier, the mental processing they have to do.

Oh, and don't worry so much about things not being "real" projects. Most employers care less about that than you think, especially now that the line between real and not is so blurred, in a world where social media reigns supreme.

Is it real if it made money or if someone else commissioned it? Is it real if it's public? Many things start out with no intent or making money but do. Many creatives hired by brands get hired because of their personal work. Blurred lines all around mean the only parameter that matters when it comes to your projects is whether you're proud of it and whether it's relevant to the employer and role.

Learn these new skills

We've talked a lot about soft skills but the hard thing about soft skills is that because they're so hard to quantify, it's hard to even recognize sometimes that you're really really great at something. I didn't realize I was exceptionally organized until very recently (and I've been in the working world for over ten years), and more than that, I didn't didn't realize that how good I was at this was exceptionally important to my bosses.

I focus a lot on soft skills because they're universally desired and they're so important to cultivate, versus technical skills that are typically specific to the role and that may decrease in relevance over time.

However, there are some skills that I believe will be incredibly important in the job market now and for many years to come.

You don't have to learn any of these skills here at all, if you don't want to, and especially if you have a goal or dream to do something else. However, these skills will make your job hunt easier and it's worth thinking about your short-term goals as a way to advance your career prospects for what you do long term.

Content production

Producing any kind of media used to be a low-salary, low-impact role, mostly because we weren't living in the kind of world we are today, where content is the omnipresent backdrop to all our lives, following us around everywhere, not just on television, film and print just decades before. If you have any kind of skill in producing content, consider cultivating it: write more and write publicly, practice illustrating, study video production and make things.

This goes for any kind of content. As the internet evolved drastically over the past 20 years, content has gone from being primarily written to visual to now video, from high productive value videos to low-production TikTok videos. There's a content rush right now and all kinds of brands are looking to cash in. That means they're hiring people who can produce, host, create all forms of content.

The key here is to look at a lot of things, learn what you like and gravitate towards, and start doing. I took this approach to learn how to become a better writer without any professional training, reading a lot and studying good writing, practicing for years both publicly and behind the scenes, and now I'm a (well-paid) writer-for-hire.

Data and analytics

Everything today is measured in numbers and metrics, and if you can learn how to help companies and people make sense of data, you'll be in very high demand.

This includes things like Google Analytics, SQL, data visualization. Data and analytics covers such a wide range of things and can apply to so many industries (basically all of them), and it can become a career path on its own or be an extremely valuable asset to any other creative role.

For example, you could combine content writing with skills in Google Analytics to amplify your impact, becoming a T-shaped content writer with a specialty in SEO.

User experience design

Every company that has a website or app, or both, needs UX designers. UX designers use psychology, research and design to craft better experiences for people.

It's a highly in demand field right now that is in fact led by really strong soft skills. So if people are your forte, all you need to do is learn how to think strategically like a designer (no, you don't have to be good at drawing) and start to use the language and tools that UX designers do. Then, put together a portfolio. You'll get hired on the strength of your portfolio, not because of your education, or lack thereof.

Since UX design isn't really a college degree you can get, most people who are working UX designers today are self-taught or transitioned from something else, which means you're not really behind at all. You are in fact in like company.

This, like everything else on this list, is great as its own career path, but also great as a side skill to help you bring a more user-focused perspective to any kind of role.

Coding

Code is the language of computers that practically drives our entire world today.

You don't have to want to become a software engineer to benefit from learning to code, but if you start and really enjoy and have a knack for it, then that does open up the door to software engineering roles, which continue to be in extremely high demand, as well as being very well paid in most cases.

If you don't go down that career path, learning to code will still be an incredibly useful skill for you to learn, whether it's working on product teams where you'll have to speak the language of developers, or whether it's being able to build your own creative projects with ease to support the growth of your own career in other ways.

Project management

Project management is sometimes considered a skill in itself, even though it's really a culmination of a lot of skills together, many of them soft skills. But I've put this here because the value of this skill and role will only keep growing as the world becomes increasingly more complex and teams more cross-functional.

If you're hyper-organized, great with people, and love to get things done, then moving deeper down this path is something to consider. There are project management certifications that you can get to brush up on the technical aspects of project management.

Project managers with a knack for business strategy can move into product management, one of the highest paid roles in tech. Or, you can take this skill and just get a lot better at managing projects and working within teams and with clients, delivering outcomes on time and on budget.

Copywriting and technical writing

Even though video has taken over the world of content, writing is still very, very important. This actually ties into how everything can be measured now, and that includes the success of the content on websites, headlines, social media, ads, products, etc.

If you enjoy writing and have a knack for it, it's worth considering learning about how to write with outcomes in mind. Copywriting is typically writing for the purpose of selling something and technical writing is writing for the purpose of educating. Sometimes they're blurred but they're also two very separate disciplines, and they require a lot of practice and skill to do well.

Learning how to write better is both an art and a science, and even if you don't become a copywriter, writing in a way that converts and gets people to read is useful for almost any job in an increasingly digital and remote world where communication is key.

A personal website, your next level resume and cover letter

Do I think anyone needs a personal website? No.

Do I think personal websites help? Yes, a lot.

And I think they help more and more now. It's becoming quite standard for employers to google candidates just to see what else comes up, like a modern, public background check.

I think general opinion about this has changed over the past few years. It used to be frowned upon, akin to stalking people. After all, people should have the right to keep their personal and professional lives separate. But like it or not, those lines are blurring. It's no longer strange to look up candidates; it's expected.

That said, I think it's totally fine to keep social media accounts private. I'd do that unless you're specifically using social media as a play to work in your favour. If not, then I'd default to private so that employers can't use anything they find against you.

Remember, in the job hunting process, they're not only looking for reasons to say yes, they're also looking for reasons to say no and to eliminate people from the pool, especially in scenarios where they've got a lot of maybes.

A personal website is a great way to "get ahead" of the googling that's inevitably going to happen, a way to do that whole preemptive storytelling thing we've been talking about this whole time.

It doesn't need much: a short bio and links to social accounts that you do want to show off.

But if you want to go next level, here are some things you can try that can build trust and klout, things that don't really work well on a more traditional and formal resume and cover letter but can give you a leg up on your job search when they're on your website:

• testimonials from people who've worked with you
• articles, resources or blog posts
• a portfolio of projects
• an extended bio
• media or press mentions

These things, if the right person come across them, can catapult you from a quiet yes to their number one candidate. There's still the interview process of course, but it's a great way to make an impression.

A pro tip: before you do a round of job applications, think back to your "story" and the industry and jobs you're applying for. Make sure that what's on your website matches up to that. It might even be tweaking one word. It might be cross-checking that what you're saying isn't in conflict to what you're saying on your job application.

For example, let's say you were applying for roles in different industries, one in fashion and one in gaming, at the same time. You're equally interested in both industries but you're not exactly going to say in your cover letter that this is the case (because remember, you're not telling them everything; you're just telling them what's relevant.) So don't write on your website that you're looking for a role in fashion. Make sure that what's on there is as specific as possible while still relevant to whatever you're applying for at that moment. Maybe it's finding the common thread between fashion and gaming and why you're interested in both, and using that instead of calling the industries out.

Your bio and story can and should be forward-facing, not just "Here's who I was and what I've done." That's largely accomplished by your resume. On your website, you have the opportunity to add in another layer of "Here's what I want to do".

Smart employers recognize the importance of hiring employees that they can retain for the long term, and if your goals match up to theirs, they'll take it as a signal that you're at least on the same page, aligned and engaged. Now, the reality of whether or not you will stay depends on a whole host of other things in the job itself, but at least you're on the right track.

Be intentional about deciding what information to highlight and what to exclude. That's a really really important skill to have when people are overwhelmed, when people skim and when people don't have time to build up a story for you. Lay it out for them.

Parting words

I wanted to write the best resume and cover letter guide I possibly could. True, I haven't read every single one but I've read a lot. It's where I picked up many of the basics. Over the years, I've honed my technique and system to great success, landing interviews and jobs with sometimes world-class companies, without much other than my very specific, vocational community college degree in fashion design.

One of my biggest gripes with so much of the advice out there is that they'll tell you what to do, even how to do it, but not why you should.

Now that you're just about done, I encourage you to give your resume an update right now, to start to package and even see yourself in an entirely new way.

Learning to write a better resume and cover letter is about so much more than getting the job. The world is made up of endless butterfly effect moments. Decisions, actions, opportunities that lead us further down paths of possibility.

You never know where the next job you'll get is going to lead you, what kind of path will open up to you that was never open before. We need more people, all kinds of people, creatives and generalists included, in all sorts of industries making important decisions helping to change the world and make more money to change the world by lifting themselves out of the ideas society, culture, bias has imposed on them, sometimes that they and we impose on ourselves.

I love the 2019 film Arrival starring Amy Adams, in which she plays a linguist who's called in by the government to communicate with aliens who've just landed in strange pods around the world. With no common language, her task is to learn to communicate with them to figure out what they want. I won't spoil the film for you here, and sure, it may be sci-fi, but the point I'm trying to make is the way we perceive things has an impact on the world we see and the world we build.

Perception is so much about presentation, rooted not in reality (because what is that, really?) but in packaging. And you have the power to present yourself and see yourself in a new way.

This reminds me a lot of the world of colour and how something like colour, something that we now think is either there or it isn't, can be invented. Before blue was named, humans didn't perceive what we now know as blue to be a colour in itself. Blue existed but it wasn't perceived. It wasn't real until we invented it.

You already exist as special, valuable, a person of impact and power. It's up to you to present yourself that way.

The exercise in starting to think of your resume and cover letter as a way to tell your story, create your own narrative and think in outcomes, is a way to slowly shift your perceptions of what work is: away from showing up and getting tasks done and into showing up to make an impact.

It's a tall order, yes, but I believe that this happens simultaneously as we get better jobs to better our own individual lives and as we get better jobs to make companies and the world around us better too.

In a world where there's so much dissent, burnout and apathy for work, writing a better resume and cover letter doesn't solve all the problems in work (obviously). But it does help more people open that door for themselves, just like I did for myself once upon a time.

People are the engine of work and of the world. Let's build an engine together made up of more kinds of people.