How to Vacation When You’re Working Remotely

Strategies to help you disconnect from work in the digital era

Alexandra Samuel
Index
Published in
6 min readAug 3, 2021

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Photo: GettyImages

It’s hard to make a vacation feel like a vacation in the digital era. Mobile phones and email mean that we’re almost always within reach of our boss, colleagues, and clients.

Remote work compounds the problem: What defines a vacation if you’re already out of the office? And how do you set limits on your availability when your colleagues expect to reach you whenever, wherever — especially if you’re in a role where it’s unrealistic to go incommunicado for more than 12 or 24 hours at a stretch?

As a longtime remote worker and one who has rarely been in a position to take a full-time, uninterruptible vacation, I’ve wrestled with this problem for years. I love the idea of spending two (or better yet, four!) weeks away with my family, but I can’t afford to go offline that long. Since I’m self-employed, the money tap switches off when I’m on vacation, and if I ignore my email for a few weeks, I may not have a lot of work to come back to.

That means I’m usually in a situation where I need to somehow get into vacation mode without turning off my phone or ignoring my email. The email strategies we discuss in Remote, Inc. help because they mean that my email isn’t out of control in the first place. But I have some special tactics I deploy just for holidays — and they’re not all about email — that will allow you to enjoy truly wonderful vacations with my family, and return to your (home office) desk fully recharged.

Here’s how:

Get off the hook with your OOO message

I had many a vacation ruined by email before I mastered the out-of-office message: not because email intruded on my holiday, but because the backlog awaiting my return was so enormous that it pretty much canceled out the R&R that preceded it.

That’s because my old OOO message followed the usual formula of, “I’ll be back on X date, and will reply to you then.” I finally noticed how many of those piled-up email messages were practically pointless by the end of a two-week vacation and decided I would no longer commit to reading them.

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Alexandra Samuel
Index
Writer for

Speaker on hybrid & remote work. Author, Remote Inc. Contributor to Wall Street Journal & Harvard Business Review. https://AlexandraSamuel.com/newsletter