Freelancer Follies: The Downsides of Self-Employment

Lancelot
The Round Table
Published in
3 min readNov 11, 2017

Every full-time freelancer hears occasional comments like, “Gee, wish I could get paid while doing my laundry.” Sure, being able to work while wearing your favorite dinosaur slippers is great. But there are downsides to freelancing that many people just don’t get.

Taxes

Gone are the days of the 1040 EZ. If you run a small operation with few expenses, you can probably do your taxes yourself. However, if you need to take multiple deductions, you should do yourself a favor and find a good CPA. They aren’t cheap, but they’ll likely save you much more than what you pay for their help.

Quarterly prepaid taxes are another snag. Unless you don’t mind being penalized every year, you’ll want to send the IRS quarterly payments of your estimated taxes for the year. If you send more than what you actually owe, you’ll get a refund when you file. If you don’t send enough, though, you’ll be on the hook for the difference.

Home, Work and Homework

Okay, enough about finances. Let’s get down to one of the best and worst parts about freelancing: working from home. Want to work at 3 a.m.? Go for it. Want to work while binge-watching your favorite TV show? No problem. But here’s the kicker: many people who work from home find themselves blurring the line between home and work.

It seems harmless at first. You take time away from your game of Freecell to answer a few client emails. You squeeze in just one last project before heading out the door to meet with friends. Before you know it, you’re actually feeling guilty for having spare time at all. The voice in the back of your head is nagging you about how you’re wasting time that could be spent working.

See, our brains like to compartmentalize. Having different physical spaces means you’re much more likely to leave work problems at work and home problems at home. Freelancers who work out of their own home don’t typically have that luxury and can start to lose that balance. It’s a recipe for burnout.

If you have the room, try to set aside an area you use solely for work. This can be a home office, a spare bedroom, a garage — whatever space you can find that’s suitable. Resolve to work only in that area of the home. Keep the door closed if one is available. Put as much distance between your home and work lives as possible in order to increase productivity and decrease your chances of becoming a workaholic.

While you’re at it, designate consistent work hours as much as you can and work only during those hours. Anything outside those hours is your time.

Isolation

Gossip, distractions and that one coworker who steals your lunch from the office fridge no matter how many passive-aggressive Post-Its you leave on the door — those problems go away when you work from home. Well, for the most part. Humans are good at finding ways to distract themselves.

What you might not expect is the isolation that can accompany freelance work. This is doubly true if much of your work is performed online with little or no interaction outside of emails. You probably won’t get to the point where you turn a volleyball into your new best (and only) friend, but you might find yourself missing those office annoyances after all. Freelancing can be lonely work, so make sure to venture out into the world now and then, okay?

All of this makes freelancing seem like a drag, huh? Well, it’s a job, and like any job, it has its drawbacks. But this information isn’t meant to send you running back to your office job. These are just things you need to be aware of when embarking on this career path. Look at it this way: at least you’ll save money on all those “don’t steal my lunch” Post-Its.

If you’re not worried about these follies and plan to start freelancing, Lancelot can help. Sign up here and start creating the best damn freelance proposals you can imagine.

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