top of page

Wear real clothes and pay yourself first: Thoughts on freelancing

When I tell people what I do, their responses usually fall into one of two categories: polite incredulity or overt jealousy. "You work for... yourself? Who even pays you? I mean, how are you, like... alive?" or "You get to work at home in your pyjamas?! That must be amazing! I've always wanted to do that!"

Many people then have more detailed questions to ask because they've thought about one day working for themselves too. That's why I thought I'd share a few thoughts that I wish (oh how I wish) someone had laid out for me when I first started down this road to self-employment.

(1) Pay yourself a living wage and pay yourself first. Be unapologetic about it. Don't allow prospective clients to haggle or lowball. Ever. The right kind of clients will be drawn to your commitment to excellence, the wrong kind of clients will balk at the price and leave you in peace—win-win.

You're never going to mention it to clients—because that would be whiny and unprofessional—but you're going to remember, always, that you have absolutely no pension, benefits, sick days, etc. More than the average person, you're going to need to learn about living frugally, saving wisely, investing properly, and paying yourself (and your future self) first. It's so easy to live day-to-day, and to feel far too pleased with yourself when a large project wraps up. But remember... do you want to be chained to your laptop for hours at a time, wrists and eyes aching, into your 50s? 60s? Even older? I sure don't.

It's no coincidence that most freelancers I know (myself included) have a spouse or partner with a "real job"—in other words, the pension, parental leave, steady paycheque, and so on that they lack. That extra sense of security can go a long way when it comes to sleeping at night but remember, nothing in this life is certain. If you're serious about working for yourself, you need to treat it like a "real job"—not a bonus income. It's part of why I wholeheartedly agree with this seasoned freelancer's advice that full-time freelancers need to charge (or work towards charging, asap) at least $100 an hour for their time. This figure wouldn't sound shocking at all if you knew what most employers actually pay in order to employ someone—especially when you consider that in an eight-hour workday, the average worker only puts in 2 hours and 53 minutes of productive time!

Finally, a quick and very necessary note on gender: the pay gap is real and it's especially wide in freelancing. Women chronically undervalue themselves and their talents. I've met editors and copywriters with nearly 20 years experience who still consider $28 an hour a great rate because it helps augment their husband's income enough for the family to afford an annual vacation. Come on, ladies. If you're amazing at something and you've been doing it for years, charge what you'd expect to pay a 40-year-old guy with a corner office, a secretary, and six weeks' paid vacation to do it. Full stop. Research what a top-quality product in your industry would cost, and then go a tiny bit higher.

(2) Work like you're the world's best and luckiest employee. In line with the above, you're not just going to pay yourself like this is your real (and only) job, you're going to work like this is your real job. When I'm feeling overwhelmed, I think of a comment that stuck with me from the creator of Humans of New York, Brandon Stanton: "Do not use following your dreams as an excuse not to work hard. Because following your dreams correctly is nothing but hard work." When you work for yourself, work truly is a gift—an opportunity to provide for yourself on your own terms. This mindset keeps me productive as well as grateful, and gratitude = happiness, which is a big part of staying motivated and, you know, living life in general.

And don't forget that you are very lucky. Self-employment opens doors that 9-5 workers can only dream of. Work from your bed, work 2 hours a day, work from Thailand, join a housesitting website and change residences every few weeks—the options are endless and you get to choose whatever suits you and your circumstances best.

Yet, this freedom comes with a hard truth: Being a freelancer requires far, far more self-discipline than a "normal" job. I say this with zero trace of hubris as it's something I still struggle with (understatement), even after almost 10 years of practice. My advice on self-discipline comes from just about every successful person I've ever heard of and it boils down to this: Just do it. Don't think, don't let your brain do more than it needs to. Set goals, get into routines, make checklists and just plow through them like a little robotic workhorse. Your paid work hours are rarely the time for creative or analytical thinking, both of which lead to wasted time and distractions when you should be in plow mode. "Make hay while the sun shines" needs to be your motto if you're going to leave the security of a set paycheque each month. And on the subject of working effectively and efficiently...

(3) Know thyself. A Delphic maxim worth its weight in gold when it comes to being your own boss.

Learn about yourself. Identify where you go wrong and how you work best. What environments, activities, routines, periods of the day, sounds, and even clothes help you feel "on" and ready to work your best?

I had a friend in grad school with a magical study hat. I mean, it wasn't magical on anyone else (to the best of my knowledge) but it worked real and consistent magic on him. He was the kind of guy who read a lot about getting ahead and cultivating successful habits so I'm sure that tip came from somewhere—no idea where, but I'll forever associate it with him. His magical hat was an old, faded, comfy-looking blue ball cap. And he only wore it to study. Basically, when the hat went on, he was in study mode. Like Pavlov's dogs, he deepened the association every time he studied while wearing that old hat. Even if he got up to make a cup of tea or take a call or use the bathroom, he took it off. If we showed up at his door and the study hat was on, we wouldn't even bother trying to persuade him to take a break.

Find your own versions of the study hat and give your self-discipline a huge hand up. Mine are glass after glass of fresh, cold water (a hydrated brain is a better brain, and frequent bathroom breaks from the screen are good for your mind and your eyes), soothing sound waves that (purportedly?) promote focus, a timer that I reset with each mini milestone reached, and real clothes that make me feel like a real employee (there goes the "You get to work in pyjamas" envy).

Coffee shops and libraries can be great too, since they make you feel a bit less like a hermit, but be considerate: I've seen full-on sales office set-ups in my local Starbucks (complete with headset, point-of-sale system, and two monitors) that have everyone in the shop rolling their eyes and tiptoeing around a maze of cords when they try to buy a coffee.

With nearly half of millennials now freelancing, it's fair to say this form of employment is here to stay, and could even become the norm one day. Whether you're thinking about freelancing on the side of a steady income or already a veteran full-time freelancer, what tips would you offer someone in your position? Any key ones you think I've missed?


28 views0 comments

Recent Posts

See All
bottom of page