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How to Take Time Off When You’re Your Own Boss

by Hanna Brooks Olsen
featured, money & life

Photo via Tommy Tsutsui.The growth of the freelance economy means two things: First, that creative entrepreneurs are ditching their desk jobs to explore the fields they really love, and are even making a living doing so. And second, that more and more of us are opting out of the kinds of workplace benefits traditionally provided by employers, and instead, are making due with what we can provide ourselves. Which, thanks to the Affordable Care Act, has gotten a lot easier when it comes to health care — but what about time off?

Sure, working from home is relaxing and all your friends are jealous, but during the summer, as they’re all hitting the beach at far-flung locations (and getting paid to do it), you might start to long for some good old-fashioned PTO. Unfortunately, in the life of a freelancer, time off has traditionally meant “time spent not getting a pay check.” So how do you go on vacation when you’re your own boss?

The first thing is to start saving early, which isn’t the best advice for mid-July, but still deserves to be said. The fact is, if you’re taking time away from work as a freelancer or small business owner, you’re probably going to take a financial hit. But if you plan ahead — book your tickets early for a cheaper rate, scout for hotel deals or stay in less-expensive digs, like an Airbnb — and stash away some extra cash to pay yourself at least a marginal amount while you’re relaxing, you can rest more easily during your actual trip.

Saving enough to pay yourself for your time off can be tricky, though — so it’s important to look for way to get paid as a result of your travels. Whether it’s taking photos that you could sell for commercial uses, photographing a destination wedding and then extending the trip, using your trip as market research by attending a craft show, or writing about your adventures and pitching them to an editor, finding clever ways to earn some money while you’re out and about can help lessen the blow of putting your usual work on hold. Plan your trip around industry-relevant conferences or other events that can result in a marketing opportunity or even direct income.

Even if you just use the opportunity to meet with a client who lives out of town, turning your travels into slightly-working vacations is a smart thing to do.

Freelancers should also be savvy about how to get things for free. Use a credit card that accumulates airline miles for the large purchases (like cameras and computer gear) that you also write off on your taxes. Consider an apartment swap with a fellow freelancer in another city — it’ll give you both the chance to get a change of scenery, and won’t cost you extra in housing. And remember to save all of your receipts; if you’re truly doing work while you’re out of town, your trip can become a business trip for tax purposes.

Finally, there’s always the option to actually just keep doing the work you’d usually do while on vacation. While this might not seem like the most fun option, it’s one of the best parts about being a freelancer — you can work from anywhere. You don’t need to put in a full eight-hour day, but committing to spending just a few hours editing photos on a lanai in Maui or writing a few blog posts from a sidewalk cafe in Paris isn’t the worst thing in the world, and can ensure that you won’t be swamped with overdue bills and a maxed out credit line upon your return.

You may not get actual paid time off as a freelancer, but if you’re clever about it and willing to work a little harder to plan your trips, you can vacate with the best of them — without landing in a financial bog come fall.

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Hanna Brooks Olsen

Hanna Brooks Olsen is a writer and editor for CreativeLive, longtime reporter, and the co-founder of Seattlish. Follow her on Twitter at @mshannabrooks or go to her website for more stuff.