Everyday you're hustling: The reality of going freelance
The Handbook / Culture / The pros and cons of freelancing

The pros and cons of freelancing

Everyday you're hustling: The reality of going freelance

Words— Marc Richardson

It’s funny—since I started freelancing just over a year ago, I’ve poured thousands of hours into research to become as close as possible to being an expert on subjects ranging from German military sneakers to split-toed boots to obscure clothing brands. I do this so that people ask me about them. That’s literally how I can survive, by getting asked to write about one of these subjects.


Despite that, the thing I get asked the most—without a doubt—has nothing to do with the subjects I’ve spent more hours than I care to admit researching. No—the question I get asked the most is: What’s freelancing like? Must be nice, huh?





So, here, once and for all, is what amounts to my tell-all answer on what it’s like to freelance full-time. But, like, real full-time freelance, not the sketchy kind aimed at flouting labour laws and taking advantage of young workers. I write this not only to enlighten those who are considering making the jump—it’s scary to give up your job!—but also, rather selfishly, to have something I can send people when they ask me the question they will invariably ask.


There’s good news—and there’s bad news. But let’s start with the positives because that’s what everybody always focuses on.



You’re your own boss


For one, it’s nice to not have a direct boss. Yes, I have editors and clients to answer to (hi, Ben!) but, at the end of the day, the buck stops with me. If there’s someone that I don’t like working with, then I don’t have to work with them. I think everyone’s had that terrible experience of a boss expecting something that wasn’t realistic given the situation—sometimes it’s hard to make assessments when you’re managing 20 people and five projects, but man does it suck when your boss tells you something’s not good enough and you’ve poured all your energy into it for four weeks. As a freelancer, the only person you have to worry about is yourself. I know when I’ve slacked off—but I also know when it’s not my fault that something didn’t work out. So—somehow—you get more slack, but you’re also more accountable.


Not having a boss also means being able to choose when you want to work. Work best early in the morning? Great. You can start whenever you want and finish whenever you want. I get very little writing done on Tuesday and Wednesday afternoons during the Champions League—and Thursdays now that Arsenal is languishing in the Europa League—but I make sure my work is done, at some point. I’ve never been even remotely stressed about meeting a deadline because, unlike at a traditional job, freelancers actually have some say when it comes to setting deadlines.





And, if they don’t, at least they get to pick and choose which projects they take on! Which is, in my opinion, the single best part about freelancing—okay, that and being able to make myself a fancy lunch from the comfort of my home. As a freelancer, you can take on the projects you’re really passionate about and turn down the ones that you’re indifferent to—unless the money makes it worth the boredom. Imagine if your boss asked you if you felt like working on something before assigning it—and being able to say no!


Plus, if there’s something that you’re dead set on doing, you can always shop it around to different clients to find the one that is the best match. Most freelancers—especially in creative fields—will say that it’s best to find a balance between passion projects, which don’t necessarily pay the best, and corporate ones that can keep you afloat financially for a few months for comparatively little work.



$$$ discipline


Of course, that brings us to the first big drawback of freelancing: irregular income! Well, it’s not a drawback per se—it’s more of a reality that one has to cope with. Imagine getting two months worth of salary in the span of ten days. Sounds pretty awesome right? Now imagine not getting any income for the next two months. It’s a perpetual exercise in rationing and fiscal discipline. Add to that the hassle of chasing after clients that let invoices go overdue by a few days… or weeks… or months. It’s stressful, to say the least, but it’s a different kind of stress.


If you’re good with money, you will realize that you can never be too good with money and if you’re not, well, you learn very quickly that what’s in your bank account might have to last you a few months. Oh—and none of your taxes get deducted at source, so you have to calculate how much income tax you owe and keep it aside for months without touching it.





Like I said—discipline.


Not only are you giving up regular income, you’re also giving up benefits like insurance or an employer’s retirement plan. Do you know how expensive medical and dental insurance is?! Let me tell you—it’s way more expensive than I was expecting. These are things that may seem like small perks when you feel stuck at an office job, but they’re definitely something that you learn to appreciate when you don’t have them. Plus, freelancing means bidding adieu to arguably the greatest gift you can get from your employer—a cash bonus.



Freelancer fraud


Remember what I said about not having a boss breathing down your neck? It also means you don’t have a boss there to pat you on the back and tell you that you did a good job. Imposter syndrome seems to be especially strong amongst freelancers, from what I’ve noticed—maybe because we don’t have a business card, or a title that we can directly point to to validate our work. So while the independence can be fun, it can also be intensely isolating.


That independence can also lead to an unhealthy work-life balance. For the most part, freelancing has been the single best thing for my work-life balance. Like I laid out earlier—I work when I want to and when I need to, while taking time to enjoy the things that bring me genuine pleasure, whether that’s watching soccer on a weekday afternoon or going to the gym. But try as I may, there’s always a little voice inside my head chanting “time equals money” whenever I’m not working. As a freelancer, you don’t get paid if you don’t do work and sometimes, it’s hard to remember that it’s okay to take some time off.





You can probably see the pattern thus far: like any job, there are perks, but there are drawbacks. Freelancing means trading sure commodities—like a bi-weekly paycheck, insurance, retirement contributions and HR—for often benefits like being able to work from home, on the schedule of your choosing and no the projects you want. It’s great. It really is. But it’s not all positive.


The stresses and challenges are different, but that doesn’t mean they’re non-existent—they’re just worth dealing with in exchange for being able to work from my couch, while eating a nice lunch, and polishing off a project before enjoying some afternoon soccer.


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