Can Indys Work While Traveling?

By Erin Ollila, Contributor, on January 16, 2018

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I’m writing this post while sitting at a charging station outside of Gate 2 in Reagan Airport. I’ve spent the past few days in a mastermind retreat with three of my closest business buddies, and I ended the vacation with a grown-up sleepover. The woman sitting to the right of me is arguing with her employer on the phone about how she shouldn’t have to work while traveling, and I’m practicing gratitude for the opportunity to be my own boss and make my own rules about when and where I work.

The truth is, I actually like working while on the road. But I haven’t perfected the work-life balance that keeps both parts of my life separate. When I’m on vacation, I’m anxious about the work that needs to get done or brainstorming ways to grow my business, and when I’m hustling at home, I’m dreaming up trips to take with family and friends. Neither option makes me feel fulfilled, so I knew it was time to try something else.

So, I planned a family vacation and made a decision to work while traveling, and guess what? I actually enjoyed it. While working on vacation isn’t for everyone, it’s worth trying to see if it’s for you. Here are five tips to balance business and pleasure while taking time to travel.

Delegate Tasks

If there’s a vacation coming up on your calendar, set aside time to analyze your workload and assign work to an employee or contractor. If you’re ahead of schedule and there’s little for you to give others to do, think about the type of work that will come in when you’re out. A virtual assistant can help you manage your email and phone calls while you’re gone. This might mean simply responding that you’ll contact them on a certain date, scheduling upcoming appointments for you or being the go-between to contact you for important matters while you’re away.

Pack the Right Tools

Working while away from your office can be a nightmare, but it doesn’t have to be if you pack well. Consider bringing a Wi-Fi hotspot (I mean, can you really trust that free hotel Wi-Fi?), a wireless charging bank, charger cords for all your devices, noise-canceling headphones, backup batteries, extension cords or any other industry-specific device. Then, don’t forget the basics, like your computer, phone, clothing and toiletries. The less you travel with, the easier it’ll be to get around. Just remember to bring the necessities (and use online tools that don’t take up space in your suitcase).

If you aren’t working with a VA, make sure you set up an automated out-of-office response for your email. Don’t forget to change your voicemail to indicate when you’ll return, and if you’ll have any access to your phone.

Get Work Done Before and After Vacation

If you want your travel time to focus more on pleasure and less on business, make an effort to get as much work done as early as possible. Complete any business tasks before jet-setting. Your clients will never complain if you turn around their project earlier than promised. But save some work for after you travel, too. While you may be tempted to get tiny tasks off your plate early, keep the smaller, easy-to-accomplish tasks for later.

Prioritize a Schedule

Want to work during your personal travel time? Set a schedule so there’s time for work and play. Let’s be honest with ourselves: If we’re spending our entire vacation working — without any play time — what’s the point of working while traveling? Why not save your money and stay home?

There are different ways to prioritize work time, so you’ll have to figure out what feels best for you. This could mean waking early and working for two hours before spending the rest of the day by the pool. For someone else, catching up with work at night may better suit their lifestyle. Others might pick and choose their tasks throughout the day, limiting work time to one or two hours only.

Make Time to Play

Knowing yourself is key to working while on vacation. If you’re the type who finds it hard to cut the cord, set up concrete rules outlining what you’re allowed to do while away. Making time for fun needs to be a priority. If you can work anywhere and plan on seeing the world, it’s paramount that you actually see it. Exploring needs to be your main goal when traveling, not work. If that idea stresses you out, start small. Take a one-night trip without bringing your computer. For a longer vacation, ask your travel partners to hold you accountable.

It’s possible to mix business and pleasure. You just have to be the guiding force and find the balance between the two. Happy travels.

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