March 16, 2011

Six mistakes the self-employed make when planning a vacation

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Like many Seattleites in winter, I've been pining for warmer, sunnier climes. As I ponder whether a vacation is in my future, I'm reminded of how much we self-employed folks get wrong with our vacation planning.

[Photo by malias]

Herewith the top six mistakes freelancers, entrepreneurs, and independent contractors make when it comes to taking some much-needed time off.

1. Forgetting that your vacation days are unpaid. As a freelancer, sole proprietor, or other indie worker, it's easy to forget that besides covering your travel costs, your vacation fund must include the income you won't be earning during those five, 10, or 20 days you're out of the office.

2. Failing to plan far enough in advance. My first few years as a freelancer, I never took a vacation, partly because I couldn't afford to (see item number one), and partly because I waited so long each year to plan any time off that I couldn't break away from my projects. The trick to tearing yourself away from your small business, I've found, is to plan your vacations six, 12, even 18 months out. That way, you have the time to both save up for your trip and ensure your clients can live without you for however many days you'll be gone.

3. Mistaking a business trip for an actual vacation. Although professional conferences can offer a great career boost, this time away from your home office doesn't have the same relaxing, rejuvenating effect as, say, zoning out on a tropical beach.

4. Believing the world will slip off its axis if you leave town. It won't. From a business standpoint, chances are nothing that monumental will happen while you're gone. And if you are in the middle of negotiating a big deal, there's always email and smartphones and interns and virtual assistants to make sure you stay in touch. Sure, it's more relaxing to unplug for the duration of your trip, but it's not always realistic to avoid email while away. Still, you can squeeze in a heck of a lot of relaxing outside that one hour a day you're wheeling and dealing online.

5. Taking billable work with you. To avoid the loss of income and break in business continuity, many self-employed folks write articles, create web pages, and do other deadline-driven projects while traveling. Although I'm guilty of this too, I've found it's nowhere near as relaxing to vacation this way -- and not just for you, but for the people you're traveling with. I'd much rather go away for five days with zero articles to write than go away for 10 days and work half the time. It sort of defeats the purpose of being on vacation.

6. Forgetting to schedule a pre- and post-trip down day. Before leaving town, many small business owners need at least a day to wrap up all those loose odds and ends (invoices, client correspondence, marketing materials a prospect requested). Likewise for catching up on emails and other correspondence upon your return. When leaving town becomes more stressful than not taking a trip at all, it's time to change your vacation planning approach.

Michelle Goodman is the author of "My So-Called Freelance Life" and "The Anti 9-to-5 Guide." E-mail Michelle at mgoodman@nwjobs.com

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