How to Take Vacations If You're Self-Employed

Higher highs, lower lows and creamier middles. Such is the life of an entrepreneur. It’s not for those with a heart condition or a weak stomach, because, unlike a “real” job, if you feel like ditching work, not only will you not get paid, but you’ll also have the nagging sensation that you’re missing something important and potentially super-lucrative.

I know from experience and from my friends and colleagues who walk this lonely path that vacations aren’t really part of the deal. I’m familiar with the grind thanks to my previous jobs steering publications: If you want to get out of town, you have to work incredibly far ahead and hope your co-workers and freelancers can help carry the load while you’re gone.

Some companies are worse than others. I’ve heard horror stories about a certain Chicago-based company that expects you to be on-call 24/7 when on vacation in case any fires break out – and it’s something that goes wrong as a result of something you left behind, you’re fired.

No wonder we’re all super-stressed and chained to our desks. A major perk of entrepreneurship is the supposed extra freedom we’re allowed.

And yet, why it is a bragging match when people discuss vacations? “I haven’t gone on vacation in four years.” “Oh, I haven’t been on vacation in six years, and I worked through my back-surgery recovery.” These are things I’ve literally heard people say.

I don’t feel like digging up the studies but I know they exist: When you take time off, you come back to work more refreshed and more efficient and, in general, just more enthused about everything.

If you feel your enthusiasm sagging, if you feel the walls are closing in: Figure out how to do it.

Mashable has a snazzy post on how to justify it to yourself. It covers a lot of what I already said, and has two other good points as well on deducting and finding inspiration once you’re there:

To deduct any travel expenses, the trip needs to be primarily for business. You can include a few days of “pleasure” in a business trip, but the primary reason for the trip needs to be work. For example, a client meeting or trade conference. In this case, you can deduct any transportation costs (plane tickets, taxis, airport parking, etc.). You can also deduct hotel and meal costs for any of the business days. Refer to IRS Pub 463for all the details on which expenses can be deducted.

Once you stop fretting about what’s happening without you, you’ll be amazed at the impact a vacation can have on your business. Time off can open the flood gates to fresh perspectives and inspiration. For example, while traveling in Mexico, Eric Stumberg hatched the idea for TengoInternet, now the largest wireless Internet provider to campgrounds and RV parks. When you least expect it, you might dream up a brilliant idea, a new way to deal with a troublesome client, or the perfect tagline for your client’s new launch.

I know that’s true – usually the best ideas will come to me when I’m not looking for them. So, take a deep breath. Get some culture. Even if you do a little bit of work while out of the office, spend less time working than you would when you’re here.

And don’t forget the suntan lotion. 

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as an interviewer-writer for Adult Swim, he's also a comedy-writing instructor for Second City. He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. When not playing video games for work he's thinking of dashing out to Chicago Diner, Pizano's, or Yummy Yummy. His first career aspirations were to be a game-show host.

Contact Us