On Freelancing
The following is the first, unedited chapter from a book I started writing and never released, on freelancing. I didn't feel right finishing and selling it because given the continuing unresolved state of my career and the tumultuous state of the market, some of my beliefs no longer feel accurate. But there a lot of ideas in here that I feel are important and that helped paved the path for my to pursue my artistic projects. So here you go.
Freelancing saved my life.
Sounds trite and hyperbolic, but it’s true. And okay, the statement is an over-simplification. But when it comes down to it, freelancing did save my life.
When I quit my startup job in 2020, the year of the great pandemic, I was so burnt out that I quit without a plan. I even transitioned to working part-time so my boss could keep me on while giving me time and space to make sure I knew what I was really doing. This was a couple months after he promoted me to a leadership role with a upgraded six figure salary to match. The kind of salary that, for a formerly struggling creative, was life-changing. He even kindly suggested taking a few months off, and then that I think about changing my role—and asked me to name any role. I had everything handed to me on a platter and though that made it all that much harder, I knew I had to leave. Coworkers asked and I told them the truth with a kind of shrug that gave the sense I was less panicked than I was: I’m not sure but I’ll figure it out.
It was the first and only sabbatical of my career so far (I justified it by saying it made up for all the years I spent working two jobs, side hustling, and working in minimum wage jobs without paid vacation). While I graduated into a recession and saw my partner and peers struggling to find jobs, I’ve always had one. There was plenty of low-paid work back then for a girl who knew Photoshop and the internet when social media was new, and the promise of a free and shiny way to market a business was not just exciting but a life raft for all the small businesses that almost went under during the one of the many apocalypses of the era.
In those six months, I got vision correction surgery, became mom to a cat, bought my first home (which I would not move into for another three years) and mostly spent a lot of time playing games and indulging my inner child. I figured: 7 years before I got a job with paid vacation, 7 years without a vacation other than the one time I went to Greece for a honeymoon in a marriage that didn’t work out, 6 months off. Sounds about right. It’s payback, and I’ve earned it. I paid my half of our living expenses out of my savings. And then the panic came back by summer. What was I going to do? I had made my great escape. As I looked ahead to a horizon that in theory was full of possibility, I couldn’t help but feel the same sense of dread: that whatever I chose, I’d be back where I started, and there was no job I could do that would give me both creative freedom and the kind of financial security I’d need living in a high cost of living city.
I’ve been freelancing since, mostly as a writer and one time as a designer slash creative director slash project manager working with my R&B recording artist client.
As I sit here looking out the window hearing the clack-clack of myself putting to screen this story, I have the opportunity to take a step back and look at where I am and how far I’ve come. An average month is me making 10k, though I once hit almost 30k in December 2022, and I’ve been making six figures every year since year one. I think about how much money I’ve made, almost half a million dollars in three years, and it seems absurd. Depending on who you are, where you live, what industry you work in, and how much privilege you started with, this may seem like nothing or it can seem, like I thought, an absurdity. If you already have a network and high value skills to leverage, you have a head start. Your mileage as a freelancer may be even higher and better than mine. And if not, then you’re kind of where I was, and this is written especially for you.
Just a few years ago, I calculated how much money it would take for me to every afford a home in my city. If inflation was not a thing, and we all know very well that it is, I would’ve been almost 50 years old by the time I could afford a one bedroom condo. Just a few years ago, I was getting divorced at the ripe young age of 27 with no career prospects, still muddling around with entry level jobs.
My life is so different today and I finally feel, for lack of a more concise way to say it, like myself. Whoever said money can’t buy happiness left out the fact that money buys freedom which is, in my eyes, an essential component of happiness. Not that happiness is how I measure my life, anyway. (There is only so much happiness I can take in one day.)
This isn’t solely about money, but I wanted to bring that up first because:
- When you don’t have it, it’s so hard to think about anything else.
- When you have it but are thinking about going freelance, money can be the biggest reason not to take the leap.
- One of the biggest perceptions about freelancing is that it’s for people in between work, a way to tide them over until the next full-time gig. Freelancing is volatile and there’s no security and it’s a shitshow in this economy, is what most of us have been led to believe. Freelancing is not a way to make money. It’s just how creative and adaptable people survive. It’s for people who can’t hack it as full-time employees.
I want to preface by saying if you’re under the impression that I’m a risk-taker or that I must be incredibly privileged to be able to quit a job without anything lined up and not even the slightest idea what the next step in my career was going to be, one of those is very untrue and the other is only half true. I decided to write this guide mostly because, while not a risk-taker, I have discovered that I’m apparently very good at something called reverse engineering. I know how to take what I want and figure out the steps along the way to get there. Doing this isn’t overwhelming to me. I get energized by it. I am also, as I’ve discovered, good at breaking things down so that they are easier to comprehend rather than attributing results under the umbrella of luck. (There’s that entry level customer support job working out for me. And the year I spent answering questions about Javascript loops and CSS selectors for people learning how to code for the very first time.)
I’ve gotten the “you must be a risk-taker” comment, implying some sort of blasphemy in spirit in sharp contrast to my soft shell. I am, I would contest, more calculating than risk-taking. Math was my best subject in school but I wasn’t particularly good at memorizing formulas. I just had a knack for looking beyond the obvious to find ways to get to the answer. That’s how I approached freelancing. I’ve had a suspicion it was how I wanted to work since I was a teenager so I’ve read probably every single resource there is out there. But once I got into the weeds I’ve learned so much more that I’ve never really read anywhere else or heard anyone else talk about.
And as for privilege? I have it (got that condo with an extra bedroom and den and a second orange cat—and I have a few years before 50). But it took time to build. I did not have this privilege at 18 or 25 or even 30.
Here’s what I believe: education is the greatest privilege. I don’t mean education = school, although it can be. Author Cheryl Strayed once said something that stuck with me. She had grown up poor and carried student debt well into her writing career, but she said that the moment she went from poverty to middle class was when she enrolled in higher education, and that it had nothing to do with her net worth. Kind of rich coming from me (no pun intended), where my version of higher education was learning a trade in a local community college dressed behind the veneer of making pretty clothes. I think, though, that the overall sentiment rings true. We’re a culture that idealizes action and risk-taking. Ask anyone to tell you a slogan and they can sum up the American spirit: just do it. But we often forget about the lead-up to that action, where we learn and how we decide what we want to do, how far we set our sights, how we change who we are before we ever do it. Education, or more accurately, learning and expanding our minds is how we change our lives. We don’t just need to see it to believe it; sometimes we need to see it to know it’s even a possibility.
That’s on the one hand. I didn’t have a lot going for me. But I did have a great capacity to learn. Learning took me from a whole bunch of entry level (that’s the downside) jobs (that’s the upside: always having a job for that stretch bookended by layoffs between the 2008 recession and the 2020s layoffs) to landing a role at a major tech company where I got promoted over and over again in succession, then when I was thinking about working at a startup, I got the first and only job I applied to. Not so coincidentally, it was an education company for creatives.
On the other hand, there’s a point where we have to decide actually just do it not just say it. Just do what? Do the thing. You know, the thing you’ve always wanted to do, the thing you’re afraid to, the thing you need to.
So there I was. Year two of the pandemic. No job. No idea what next. Excitement at first, yes. Cue Natasha Bedingfield’s Unwritten. Then the existential what am I? It was time for me to go for it.
I had ideas. Creative projects, maybe a total career pivot. I entertained going back to school because I love to learn but decided against it because everything else about school felt restrictive. I wouldn’t be able to make a living going to school full-time and I couldn’t bear the thought of extending my dream of (micro) home ownership into my 50s. I had a small financial cushion but not enough to just not work for two years living where I do without draining the bank account I worked so long to pad, unless I wanted to start back at the zero I’d been so accustomed to and decided I’d never want to get back to ever again. Cue me dreaming about moving to Asia, then cue the desperate Sylvia Plath fig comparisons when I decided not to but wished that somewhere an alternate universe me had.
I look back and think lovingly upon this time in my life as my delulu era during which, yes, I did wear a whole lot of Lululemon to feed my delusions in utter and absolute comfort. I saw people online boasting about making millions and thought, maybe that could be me. I did a whole bunch of career exercises, I redid Strengthsfinder, I even looked to horoscope apps for direction—and when so many of them said to go back to your childhood for clues, I obliged and then jotted down “make movies” and “go back into fashion” in my journal. Everything seemed like a possibility and yet, nothing was.
Eventually, I got real after indulging my imagination enough to start to feel the financial pinch and decided to go back to the inkling that had been nudging me for a few years. I decided to follow what I call “the current”, the sweet spot between what you love to do, what you’re good at, and the forward momentum of external forces like the state of the market, other people’s opinions, and what people will pay for. It’s where your flow meets the world.
I became a freelance writer.
In the summer of 2021, I got my first gig after hanging up my internet shingle. I think it was a single Instagram post. I called my company Wondermachine. At the time, my brain was still grasping onto tech notions of success, which include endless notions of scalability and growth. So I started freelancing with the intention that I’d eventually build an agency.
For the next three years, I went on to make six figures every year, reaching financial milestones I didn’t think were possible. The month that I made almost 30k, I’m pretty sure I was working a bit of overtime but most weeks, I spend less than 20 hours on work and sometimes way less. That means I now make more money doing about half the work I used to. This is no four hour work week, but even I have those seasons, where I’m barely working some weeks and never feel the financial pinch of taking time off. (Disclaimer: once. I felt the feast and famine cycle once. More about that in the money module.)
Some months were crunchier than others. But I’ve rarely ever felt the same constant grind as I did when working any of my full-time jobs, which always felt like a never-ending “prove yourself” hamster wheel. The major letdowns and internal worthiness debates when you’ve done it all right and get a 1% raise against a 7% inflation rate. The dopamine hits that keep you in the grind when you get the gold star, usually one person’s word—and then you become that person giving other people gold stars.
So little of that actually matters.
When I first started freelancing, I crunched some numbers and looked at how much money I’d have to make living where I do in a high cost of living city and to be honest, it seemed impossible or at least, very, very far away. I panicked and even applied to a job and interviewed for it because I told myself there was no way I could do it. I called my real estate agent and asked him about backing out of our purchase because I didn’t think I could make enough money as interest rates started rising rapidly, almost doubling our housing costs.
I had no idea it would come so fast and that I didn’t have to resort to any of the dreaded tactics I hear about all the time (the cold pitch, the networking, the sales calls—just say kryptonite for introverts). Because in that three year timeframe, my entire life changed.
The cats. The travel. Home ownership. Owning my time. I’ve arrived at a stage in my life where I look around and people are getting older. Time feels more precious. I am now able to do what I want, to help the people around me, to take my cat to the vet or visit my elderly parents on a weekday without having to report it to someone else.
This isn’t just happiness—I’ve had ups and downs. It’s independence.
Writing all this down is nice. We all forget about what we have when we’re living in the day to day. There is always greener grass somewhere else. Things aren’t perfect and I have way more I want to do. But I can unequivocally say freelancing has taken me much farther than the me of 3, 5, 10 years ago could’ve imagined. I can’t believe it mostly because I spent so long struggling to find my groove and trying to save a dime only to move two steps back.
But maybe far isn’t exactly the right word.
I quit the corporate world because I realized it wasn’t further and higher I wanted to go. For so many years, I had felt so stagnant I believed that more than anything, I wanted to work at a company with endless potential for growth, high salaries, and insert sparkly emoji: benefits. I wanted to work somewhere my mom could tell people and not have to go into a whole spiel trying to explain what the heck it is I do.
Then I discovered endless growth was kind of boring, but also stressful. That’s not a good combination. (Also: One person’s boring is another person’s security. One person’s stressful is another person’s “engaging”. I’m just speaking from my perspective.)
Through all of my experiences, I realized that I just don’t fit into a prescribed way of work. I have to make my own way of work, custom designed for me. Granted, I already had a fair amount of flexibility having worked remotely for years at that point. I also favoured startup environments so it wasn’t like there were a ton of rules; we made things up as we went along. Still, I couldn’t help but feel stifled by the idea that a company, in a sense, owned me for 40 hours of the week. There was the work, and then there were all the meetings, the strategy talks, and the team-building. All things that I liked individually, and were great on a resume, that I even had fun doing, but that still, I didn’t prefer to do over every other thing I could be doing with my time.
There was nothing wrong with the companies I worked for. I chose them and was very selective about my job hunt, only applying for companies that I valued and believed in. That was and will always be a given for me. So it wasn’t the company. It wasn’t the job, because I’ve never had the same job twice.
Basically, it’s not them, it’s me. Well, maybe it’s a little them. Work is broken in so many ways. And all companies, as I’ve discovered, have some sort of chink of their armour. There is always something wrong. But there’s nothing wrong with that. That’s just work, isn’t it? I just preferred not to work that way.
I’ll always remember the softly delivered but harsh advice of my boss at the very first job I had working at a photography studio when it seemed obvious I couldn’t be making minimum wage as a photography assistant for the rest of my career. I must have been giving off the vibe that I wanted to do more. Either that, or he’d googled me and found my blog where I never wrote anything unprofessional but where it was clear what my interests and ambitions were. Meanwhile, a coworker of mine had just quit to start her own photography business. The difference between us was that she was what some might refer to as a go-getter, and I was what my boss referred to as quiet and obedient. I was not the picture of entrepreneurial drive and hustle. So I shouldn’t have been surprised when he told me that I shouldn’t start my own business, that I should try working at a big company because I’d probably do well. He was right. After I left, then worked at another small business, and then left that, I did do well. Didn’t mean it was what I wanted. In fact, the better I did, the more I got promoted, the more attached I became to the environment that rewarded that attachment, and the more discontent I was.
I stopped believing in the corporate machine as a compass of productive morality, and started believing in my own desires and what I wanted to contribute based on my own idea of a good life. Deborah Levy wrote in her memoir, “Real Estate”:
We do not have to conform to the way our life has been written for us, especially by those who are less imaginative than ourselves.
Corporations are invented. Industrialism is pretty new in the grand scheme of things and like almost everything else other than poetry, art, and music, could be a temporary blip in humanity. How we work today was a decision someone made at some point in history that we’ve for the most part not stopped to question.
If you’re reading this, maybe you want something different for yourself. And it doesn’t matter how you got here, whether it was by choice or by circumstance. Maybe it took getting laid off to realize there’s no such thing as stability. You are here and you don’t want to do that climb anymore. Maybe you’ve already tried freelancing because you like the idea of it but you’ve been struggling to make it work. Maybe you’re here because you’ve tried other things and they didn’t work to get you where you wanted to go.
While I was freelancing over the past three years, I was also working on other creative projects hoping that something would stick. Here’s some of what I’ve tried:
- I tried to make a living writing on Substack. If you’re not familiar with Substack, it’s a newsletter and blogging platform-in-one, and where all real writers in the age of internet go to make money or in their words, “where writers earn a living doing what they love”. Patti Smith, Roxane Gay, and Cheryl Strayed are all on Substack. So are thousands of other writers who have now found a way to build a sustainable living by writing directly to their audiences. Me? I spent hours every single week writing, editing, publishing, only to have a small handful of subscribers and when I turned on paid subscriptions, that netted me a grand total of a few dollars a month. Certainly not enough to make a living, barely enough for a coffee.
- I wrote a short ebook. I wanted to see if I had the grit to even write a book and get it out there. I did. It brought some money in and as I’m writing this, I’m hoping to tackle writing an updated version of that book to launch later this year. A random stranger who found my work through Gumroad, the platform I host this book on, bought it two years after I published it, then wrote me an email telling me it was “incredible” and that it was coming from someone who buys a lot of ebooks. An ego boost, sure. But not a way to make a living without the audience to support it.
- I tried for a short while to get back on social media after falling out of love with it, particularly Instagram. I put together countless social media strategies having done this for work for big brands and tiny ones, and even hired a consultant and then a virtual assistant to help me execute. I thought I had all my blind spots covered and after months of consistent posting, hashtags and reels (of course), I netted a grand total of 4 new followers. More than that, it just felt like drudgery and submitting myself to the constant disappointment of validation by algorithm.
- Honourable things-I’ve-tried mentions: a poetry book, NFTs, dropshipping. That’s not including all my side hustles in the decade or so prior.
That’s the stark reality of trying to make a creative living. We see the viral success stories and think, why not me? But the internet isn’t a wild west. It’s a carefully tuned environment owned by a few big corporations trying to squeeze all of us out of our attention, a type of attention that is partly held up by the dreams we are sold and partly by memes.
Now, to be clear, I’m not saying you can’t just go ahead and make a living being yourself by making content or sharing your work online, a.k.a. the new gatekeeper-free way to be a creative. You can. People other than me have done it. But it’s not as easy as it looks. And that stuff takes time. Consistency. A social media presence. Some might say a certain je ne sais quoi. And just because there are no gatekeepers, doesn’t mean you’re not at the mercy of something else like an unknowable, unhackable algorithm. Think about it: if success by algorithm was that easy, then everyone could go viral which would mean that nothing is actually viral.
These pursuits weren’t all wastes of time. I had fun, I learned lots, I built things. And what I can only hope is that what I made was appreciated and valued by the few people who bought it. There’s pleasure in that. But I could never detach myself from the idea that I needed to make a living and as someone who has had to fully support myself, it’s not something I can forget: I needed to make money.
Freelancing has been there for me. Freelancing has allowed me to work on these projects while giving me back evenings and weekends and even middle-of-the-days. Freelancing has helped me move from one model of working and living to another. It’s given me the time and energy back to think about things other than making money. To live according to my own rules. Not a coincidence: I started reading 100 books a year exactly three years ago, the year I started freelancing full-time. Freelancing is not as shiny and cool as a Substack or having a million Instagram followers, but freelancing done right—your way—opens doors to change lives. And don’t believe the anti-hype: those who are smart and strategic, creative and adaptable can and will find more out there. More clients, more money, more time, more fun. The world is always changing and as the way of work continues to crumble, freelancing is here to stay.
The Perks of Being a Freelancer
Virginia Woolf famously wrote in 1929 that “a woman must have money and a room of her own if she is to write fiction.” Since then, practically an entire genre of literature has spawned, playing off this concept and phrase. Books with titles that take inspiration from this line: A Room Of Their Own, Spinster: Making a Life of One’s Own, A Life Of Their Own. Why has this idea latched on?
Because like Barbie so aptly identified, so many of us are treated like and thus perform as dolls within a society that doesn’t value our minds and ideas. And like Greta Gerwig’s Barbie correctly pinpointed as an alternative: I want to do the imagining. Virginia Woolf was mostly writing in the context of female fiction writers and artists in the Victorian era, but let’s pull back a bit. Writing fiction is imagining. But so is building one’s own life, making new laws, engineering cities, plotting an escape route, baking cookies.
So is freelancing.
Let’s first get on the same page on what freelancing is, exactly. It’s simple and as a concept not at all glamorous: a freelancer is just someone who works not for one single employer but who is running a business and works per service or contract for multiple companies or people. Doesn’t sound all that romantic, but the idea is that you have freedom and independence to choose who you work with, to work when you want and where you want, to make however much money you decide to as long as someone is willing to pay you for it.
Freelancing is a way of work without anyone’s constraints but your own. In theory, at least.
The challenge is that in practice, the perks of freelancing often get dampened by the limits of our imaginations, which caps our capacity for planning and action in the direction of possibility. We set ourselves up for failure taking the path of most resistance because it’s the path we know. Example: doing high-effort, low-paying work.
But, Virginia Woolf was right: certain conditions about our lives must be met before we have the capacity to imagine. Cue the chicken or egg scenario and probably why she wrote an entire thesis on the topic, and why it’s continued to resonate nearly one hundred years after it was first delivered as a lecture. It’s not easy—and that was coming from someone who was considered a woman of privilege and affluence.
A lot has changed in the last one hundred years but frankly, a lot has stayed the same. One underlying idea that remains true to this day is the impact and value security and independence can have on a person’s capacity to be their fullest, truest expression of themselves.
Is it possible to find exceptional and rare human beings for whom this is not true? Yes. But as I’ve gotten older and wiser, I’ve realized how much of our reality and perception is skewed by the narrative machine of PR. Read any success story and you’re likely to notice that no matter how much built-in privilege someone has, the story always focuses on lack and what one doesn’t have. The underdog story, the story of struggle, sells.
For example, Vera Wang’s undisputed status as the bridal gown designer is always told through the narrative of someone who had no experience or background in fashion design, who successfully changed her career at 40. In reality, she came from an extremely wealthy family, was given $1 million by her father to start her brand, and had a long career in the fashion industry as an editor where she was in fact very successful and well-networked. In fact, at the time she was the youngest ever editor of Vogue and her close friend was Ralph Lauren. She is an outlier of both talent and wealth. Being an editor likely gave her an upper hand amongst the many thousands of wannabe fashion entrepreneurs that graduate from design school every year. But all this is only in the subtext. The hook is always: if Vera Wang can change her career with “no prior experience” at 40, you can too.
Think about it: How many success stories have we heard from people who “started with just their laptop” or “started from their kitchen table”? I didn’t used to question it. I thought, wow, they’re just like me, we both have just laptops and a table. It’s not not true. But it’s nowhere near the full picture.
I started my Substack in February 2022. It wasn’t my first so I wasn’t exactly a Substack newbie. After six months of working on it for hours a week—something, which, by the way, I was only able to do because I was freelancing successfully—I stopped seeing traction. So, I dove into heavy research mode to analyze what other people were doing right that I was doing wrong. The answer wasn’t clear cut. I read all the how-to guides but everywhere I looked, I saw examples of very successful publications that clearly didn’t follow those rules. I finally understood that many of these people already had security and independence as creatives; many simply took their existing audiences and monetized them by bringing them to a new platform. Were there examples of successful Substacks that started from scratch? Of course. There are always exceptions. But it’s usually either a much longer or much harder slog.
Realizing this was so important: I am not exceptional. I thought good idea + strategy + hard work = success. I thought it was a given that I’d “win” the game. I had all the tools, the experience, and, from what I’ve been told my entire life through report cards and teachers in school and then performance reviews as an employee, the “talent”. I knew I didn’t have a lot of grit, with a tendency to jump from one idea and interest to another. So I forced myself to be a bit grittier. That didn’t work. I still have my Substack but let’s just say that at least for now, it was not the holy grail of creative success that was promised for someone like me, by most definitions of the word, a writer.
I don’t bring that up to challenge anyone’s success or to give you a reality check but to put what is possible and attainable and within your control in front of you. Getting to do what you love and making good money from it is hard but I think it becomes loads easier when you stop spinning your wheels on the promise of exceptionality under the guise of “everyone can do it”, and the even more difficult to swallow “everyone can do it because they did”.
Maybe that is a reality check.
I hope it’s freeing to know how much easier it is to be a freelancer providing something of value to someone else, one company and person at a time, than it is to build something that requires a large audience or even 1000 fans, as they like to say, or to work for a single company that owns your worth entirely. I know because I’ve tried it all, that Substack and multiple other little ventures. It doesn’t mean you shouldn’t ever build (you should) or that you can’t contribute to the success of companies you love (you can always buy their stock, support their products, become an affiliate—there are so many ways other than working as a full-time employee).
Freelancing is what worked for me. Not to say that everything else doesn’t nor that it never will. It could. But I don’t bet on the promise of consistency, wait on the algorithm or someone else to choose me. I do what I can with what I have now. I’m building a life of my own starting now.
Here’s why freelancing done thoughtfully is the best path to earn that much-desired and ever-elusive security and independence, to take that first important step into time, money, and creative freedom, and to create the life of your wildest imagination.
You don’t need followers.
The biggest perk of freelancing, to me, is that you don’t need to wait to go. Not for anyone or anything, and definitely not until you reach x number of followers to be able to convert the minuscule portion of people who even see your posts into people who will actually pay you money and not just dole you a like for validation once in a while.
And anyway, is it just me or is it a weird assumption nowadays that a) everyone wants to have a big social following and b) everyone can have a big social following? This is the prerequisite for so many business models that involve building an audience and while not impossible, unless you happen to be very skilled and operating in a trending niche, usually takes a very long time and a lot of consistent effort, not to mention that you need to have the personality to handle being an online persona and everything that comes with it.
I’ve been writing on the internet for about 15 years, give or take, and as of this writing, my peak has been 2800 Instagram followers, the vast majority of whom never see my posts, and approximately 500 email subscribers. Results will obviously vary but I think what I have above is realistic and likely more probable than the “I gained 10k followers in 3 months” stories which, of course, do happen—but you’d be betting on being exceptional which by definition you most likely aren’t. (Sorry!) Again, we always hear about the successes and the algorithm needs successes in order for people to keep making content to be one of the few that make it. We don’t ever hear about the people who didn’t make it, the endless ghost towns of abandoned accounts.
Freelancing, on the other hand, doesn’t require you to be a social media influencer or even to have a social media presence. I do think you have to be online and to have some sort of presence on the internet, but more on how to do that to get clients, not just likes, later.
You are offering something of actual value to someone who needs it.
I’ve seen every internet scam and MLM scheme out there. I’ve fallen for a few. There’s a whole cohort of people who spend all their time and money building out sales pages to convince you to buy something, only to fill their product with generic, recycled, pandering advice that you can very easily find for free elsewhere. I’ve seen promises of how to make money online which are just MLM schemes in disguise where, again, all that energy and effort is put into a very enticing sales and lead funnel to draw you in, preying on your psychological triggers, only to share with you once you buy that the best way to make money is to sell what they sold to you to other people. (I mean that literally, not as a figure of speech. They want you to sign up to go on social media to sell their product and make a commission off of it, all the while not telling people what the big secret is until they buy, that you’re going to tell them to go on social media to sell the product which teaches them how to sell the product to even more people. Yep. It’s a mouthful.) And on and on it goes.
Freelancing is just you packaging up a skill that someone else needs. It’s work but amidst all the get rich quick and become an influencer schemes we see nowadays, freelancing is ironically probably the fastest path to making a sustainable living doing something that you feel good doing that someone else tangibly benefits from.
If you’re like me and want to make money but to do it in a way that brings genuine value to other people (and trust me, there are so many ways to define value, but it isn’t going to be me playing into this whole internet scam culture), freelancing is it. Make money in the day, sleep better at night.
When you build it the right way, freelancing is stable.
One of the biggest reasons many people tend to shy away from freelancing is that it seems in opposition to the concept of stability, something so many of us desire in a world where so much of our lives seems anything but. The idea of just showing up, clocking in, and doing the work and not having to worry about whether or not we’re going to be able to pay the bills is enticing. It feels like a lot of pressure to be thinking about where the money is going to come from, on top of everything else we have to worry ourselves with just to live. If you have kids, pets, or someone else who depends on you, that pressure can be enough to make stability the number one perk of having a job.
Is freelancing inherently unstable? The answer isn’t clearcut.
In recent years, mass layoffs have happened in almost every sector, many happening in industries that promised exceptional growth. We hear nightmare stories of people who’ve spent months and even a year or more looking for jobs. If you have a job you consider safe, it’s still possible that you feel daily anxiety and burnout. Is that the picture of stability now?
Freelancing on the other hand is just different. I like to think that it gives you more control but of course, those who aren’t strategic about it will feel as though freelancing feels more like spiralling out of control with no ground underneath them. Think of a freelancer like a bird who flies frequently and knows how to find the worm. Yes, they have to hunt but they’ve got a great lay of the land, are strong fliers, and understand the patterns of nature and survival. Compare that to a bird who’s been fed by mama bird for its entire life. Mama bird says I’m leaving one day, no warning, and this bird has to figure it out. We hope they can.
I’ll mention here that I have tips on how to build systems so that even when you aren’t actively working, you’re still making money. And no, we’re not talking about passive income. We’re just talking about being smart with how you set up your cash flow. More on that later.
Freelancing allows you to charge your own rates, and to give yourself raises.
Speaking of cash, this is one of my personal favourite perks of freelancing.
Have you ever experienced the utter disappointment and helplessness you’ve felt when you’ve given the entire year your all at a job, have talking points for your annual review, are even given an exceptional performance rating, only to be told: it’s not in the budget or we have to spread out raises amongst all managers (which, fair, because I don’t want it to be a competition between me and my coworkers). And you can’t do anything about it because hands are tied, budgets are fixed. Tell that to inflation, which just keeps going up. If you’ve never experienced this, maybe you’ve been at jobs where there aren’t even performance reviews or raises. Ever. I’ve been there too. Or had coworkers who made double or triple what you did not because they were more valuable but because they have roles that inherently have different pay bands.
Salaries always feel like such an awkward and arbitrary dance. Sometimes it feels like the only way to make more money is to do as modern career advice suggests: change jobs as often as possible because that’s the best way, statistically, to make more money. But I have to say, and I think many people feel this way: job hunting is one of my least favourite things to do.
Freelancing is an entirely different thing. Sure, you have to be aware of what you charge so that clients are willing to pay but I’ve found it’s much easier to communicate and demonstrate value than it is to try to wiggle money out of a “fixed” budget. And if something’s not working, you can change it. Is it really that simple? Maybe not but take it from me: it was much simpler than I could’ve imagined it would be once I was on the other side.
Pricing doesn’t have to be this precious thing that defines our entire worth. It’s just business.
Freelancing allows you to take time off anytime and for however long you want to.
Why not? You’re your own boss. I schedule time off in advance, and then simply schedule client projects around it. You don’t even have to tell anyone what you’re doing. No one would know the difference between you going on vacation and you just being booked up with other work. Not that it matters if you did go on vacation.
The difference is: you can, within reason, take as much time off as possible. You can work wherever you want. If you wanted to travel and work, you can do that.
In the last three years, I’ve taken several one to two week vacations, shorter days off at a time, and regularly work four or four and half day workweeks. I’ve also taken months off at a time usually after working with my long-term retainer client for several big projects back to back.
The system isn’t totally perfect: I don’t have anyone to cover for me if I’m sick and have a deadline. But it hasn’t ever been an issue. It’s definitely not something I’d want more over having total and complete control over my schedule.
Freelancing is a fast track to building leverage if you ever do want to go back to full-time employment.
Some people assume that once you become a full-time freelancer, if it ever doesn’t work out for whatever reason, it becomes really hard to sell yourself as an employee. I haven’t had to do that but I don’t think it’s true.
In fact, there are so many reasons freelancing can help strengthen your resume. You work with a wider range of clients typically, which means you have more flexibility and transferability when it comes to applying to different industries.
I write more about this in my guide, How To Package Yourself, but essentially, you just have to learn how to position yourself and your skills in a different way. And freelancing could actually help you differentiate yourself in a increasingly competitive job market.
You can work on a wide variety of projects.
Variety of work is one of the biggest reasons I thought freelancing would be a good fit for me. I’ve worked in many different types of jobs in companies of all sizes. I identified pretty early on that I enjoy helping companies and people grow, but always seemed to reach a point where I’d end up itching to move on to another project. I love the strategy and build portion of most projects, but it’s harder for me to get excited about maintenance. And this manifested as burnout every single time. When I started writing seriously, that helped fulfill part of the itch because I got to write about different topics but eventually that started to feel stagnant too.
I can’t help it. I just prefer to work on different projects for different companies. I enjoy learning about different challenges and helping to solve them for different clients. If that sounds like you, freelancing is built that fulfill that itch. And keep in mind that variety can mean so many things: from where you work to how you work to what clients and industries you work with.
It’s not necessarily better than working for one company on one goal for one extended period of time. It’s just different.
You can always keep growing.
Human beings are wired to want the shortcut. I’m laughably not an exception, having tried nearly everything to fast track my way to success, with mostly questionable results. Until I started freelancing full-time.
I truly underestimated the impact and momentum you can gain by increasing the stability and independence of your work life, one that otherwise aims to squeeze every last ounce of us for the profitability of the corporate machine. Work is a major part of our lives, but it shouldn’t be, IMHO, Monday to Friday, 8 hours plus commutes for most people. That leaves a sliver of our evenings after basic maintenance is done to enjoy ourselves. And that’s not even counting kids if you have them. We’re so exhausted that we zone out in front of our phones and then more time passes by, and years pass, and we’re still where we were, just with more responsibility. I already feel the pressure of time; I don’t need work to add to that.
Once you have a career you fully own and control, you can keep going. It does not mean you stop growing and changing. In fact, it could be the path to more growth and change. You can change your mind, scale your business, learn new skills, or simply opt out and just enjoy the extra time you have.
Of course there are considerations to make when you move from the default way of work to freelancing. You have to think about health insurance, you have to think about where you’re going to work, you have to be okay with being your own boss all the time.
But my point is: freelancing isn’t the end. It’s the beginning.