Despite the best intentions of self-employed people, it happens. That magical, far-flung retreat we planned six months ago is just days away and, due to the somewhat unpredictable nature of small business ownership, we need to take those last few dribs and drabs of work along with us.
If you’re a self-employed person who’s new to this predicament or wondering how you might handle it better in the future, I’ve got your back. As a longtime freelancer, I have a Ph.D. in taking work on the road. Here are my best recommendations.
Get the biggest pieces done before you go. Do whatever you can to avoid having to finish that white paper or website design during your vacation, stuck in some hotel room, the beaches of Hawaii beckoning outside your window. Give the project 90% instead of your usual 110 so you finish faster. Order takeout and get someone to walk your dog or take your kids on a playdate so you can stay focused. Leave any small, lingering administrative tasks — invoicing, correspondence, quick revisions — for after your departure.
Finish work as early into the trip as possible. Do it at the airport waiting for your flight, on the plane, or — if you must — on day one of the trip so you can spend the rest of your getaway relaxing. Let travel companions know you have to work a little so they’re not blindsided (and rightfully peeved). Send them to the pool without you so they’re not stuck in the hotel room watching over your shoulder until you finish. Better yet, take your work poolside and finish with a refreshing beverage in hand.
Set aside short blocks of time for loose ends. Every self-employed person knows that setting their vacation auto reply won’t necessarily ward off important emails requiring a prompt response. An exciting new prospect may contact you about a potential project. An important client might hate to bother you but nevertheless has an urgent question only you can answer.
Rather than stay tethered to your phone throughout the trip, set aside a short daily window (I’m talking 15 minutes or less) to reply to urgent messages as needed. I like to take care of this in the morning before setting out to enjoy the day. Lunchtime or evenings may work better for you.
Once back home, reassess your pre-trip schedule. If work keeps infringing on your vacations, set aside some time when you return home to examine why. What can you do to prevent this from happening again? Perhaps you should plan to wrap up work two to three days before traveling, leaving a 48- to 72-hour cushion for unexpected project complications or personal melodramas that arise. Perhaps you need to take on slightly fewer projects the month before a big trip. Perhaps you need to outsource less important tasks to an assistant.
Or, perhaps you aren’t as committed to relaxing and recharging as you think you are. If you’ve tried all the above and still find yourself working on vacation, consider this: the more concentrated, uninterrupted time you spend unplugging and unwinding while away, the more equipped you’ll be to rock your business when you return home.