Entrepreneurs prize the independence that owning a business confers. Often, though, the big tradeoff for that freedom is not having free time. More than half of business owners take just one vacation a year, and 75% say they work while on vacation.


We asked business owners what strategies and technology tools they use to keep in touch, stay organized—and still “get away”—while on vacation.


When I’m traveling, I ask employees and contractors to communicate by email, so I can set aside 45 minutes to an hour sometime in the middle of the day, and again at night, to work through them all. It’s crucial that I have access to our customer relationship management database. I can communicate with my staff through that and also see what they’ve been working on during the day. —Garrett Ball, 65Medicare.org, Clemmons, North Carolina


I use Tidio, a chat function that allows customers to converse with you as they navigate your site. This has made it easy for me to answer customer inquiries on the go via my mobile device. It also reduces the number of email inquiries, which are a bit more onerous to answer when you’re not at your computer. I use Airtable, a super-easy way to make custom spreadsheets and trackers, to make a comprehensive vacation plan that my team members can easily follow and I can check periodically for peace of mind. —Ally Compeau, Woof Signs, Waterloo, Ontario


The law does not get put on hold simply because I’m on vacation—I have to take calls from clients and employees all the time. The most important device I use is the Apple Watch. It lets me take calls, write messages, read emails and receive alerts. It keeps my hands free and it’s always on my wrist, so I don’t have to worry about forgetting it or having it get misplaced with luggage. I do bring my laptop on trips, but I don’t take it out of the hotel. —Jesse Harrison, Employee Justice Legal Team, Los Angeles, California


When out of the office, I use Skype to communicate with staff. It allows me to do videoconference calling but also allows me to send them messages that don’t have to be responded to right away. We use Dropbox to sync and share files. I’m a huge advocate of remaining as “lean” as possible as a small business owner, and tools like this allow you to work (and vacation) in different locations without losing the communication needed to keep things running smoothly. Damon Duncan, Duncan Law, Charlotte, Greensboro and Winston-Salem, North Carolina


I recently went to a medical device conference in Korea. The biggest single help was WhatsApp [messenger app]. I love Google Docs so the team can work together from anywhere; and when Gogo [in-flight broadband] internet works, it’s great, but it’s the iffy-est of the three.


I was hiking in the Dolomites and my friends were making fun of me for leaning over the mountain with my phone trying to get signal. Sometimes you just have to trust you’ve got good people back home and relax. Amy Baxter, MD, MMJ Labs, Atlanta, Georgia




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