I
t’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 your 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.

Instead, my OOO messages now say something like, “I’ll be back on X date. Please email me after that date if it’s still relevant.” If I’m concerned about missing something important, I’ll add a line like, “For urgent matters, please contact me on Twitter as @awsamuel or by mobile at [xxx].”

I’ve hardly ever had anyone take me up on that offer, and when I have heard from people with urgent messages, I’ve been glad they reached me.

Limit (but don’t avoid) email

I know lots of people swear by email-free vacations, but I don’t find them remotely realistic.

I use email for so much of my travel arranging that turning it off would make it very hard for me to find crucial information like hotel reservations and flight times. And I always worry about what email I might be missing.

A more feasible approach is to set very tight limits on email and create some speed bumps that help break the habit of constant check-ins.

I have a separate (secret) email address I use only for vacations: I use it for travel logistics. When I had a full-time assistant, I gave her that email address to forward any high-priority or urgent correspondence. That allowed me to remove my primary email address from my phone (so I wasn’t tempted to check it), knowing that my assistant was reviewing incoming messages and forwarding what needed my attention.

On vacations where I’ve needed to monitor my primary email account myself, I still remove access from my phone; I just set a designated window every day to sit down at my computer and do a quick scan for anything vital. It’s less relaxing than unplugging altogether, but 30 minutes a day of looking through my inbox makes it easier for me to relax for the other 23.5 hours.

Get out of town (cheaply)

A change of scenery makes a big difference when you’re working remotely. I get the appeal of a staycation when you’re an office commuter: It must feel like a luxury to get along, uninterrupted stretch of time at home!

But I spend enough time at home, which is why our pre-Covid lives included at least one longer (2 week+) trip per year, plus three or four shorter (long weekend) getaways.

The secret to making that work financially? Home exchanges. We’ve taken lots of fab vacations by swapping homes, and while I’ve tried just about every home exchange site out there, our best results have come via Craigslist. I’m pretty careful about checking out our potential exchange partners (via phone and social media), and we’ve never had a problem.

In more recent years, we’ve also rented out our own home on Airbnb to pay for a rental elsewhere. Admittedly, it’s quite a bit more work to get our house Airbnb-ready (I feel like our house has to be much cleaner and emptier for rent than for a swap), but it’s a good excuse to catch up on deep cleaning and purging — which makes my home office much more delightful when we return.

Define a staycation with a fun project

It’s harder to get into vacay mode when you’re staying in the same place where you live and work… but it’s not impossible.

Thanks to Covid, I spent my one extended vacation of the past 18 months right here, hanging out in the very room that usually serves as my office. Since I’m not very good at gearing down — especially when I’m at home — I’ve learned that the best way for me to get out of work mode is by picking a fun non-work activity to keep me busy.

I’ve taken vacations organized around sewing projects, home improvement projects, and this past winter, gift wrapping: I confess that my one big vacation of the past year was spent going seriously overboard on my holiday gift wrapping. But it was lots of fun for me and switched off my work brain, which was the whole point.

Change your social (media) habits

My online life is a big part of my working life, which means it can be hard to feel like I’m in vacation mode when checking in on Facebook or Twitter. But weaning myself off social media is a recipe for a miserable vacation: I’m so used to sharing moments of my day online that I get listless and anxious if I have to stop. (Yeah, yeah, this is what therapy is for.)

My solution is to put my social-media existence into play mode when I’m on vacation. I don’t post work-related updates — no, not even by scheduling posts in advance, because that means I see a bunch of work-related replies that take me out of my vacation brain. Instead, I post only updates related to our vacation playtime, and I shift my attention away from posting to LinkedIn and Twitter (my usual online homes) and towards Yelp and TripAdvisor (where I rarely post except on vacation.)

All those social-media posts then become a way for me to extend the vacation when I get home. For most of our big vacations, I’ve created post-vacation albums that compile our Yelp reviews, Facebook updates, and vacation photos into professionally printed photo books.

Some of them have been quite elaborate. When we took our kids to Paris, I saved mementos like our Eiffel Tower tickets and pasted them into blank spots I left in my photo-book layouts. And a few years ago, we logged our Washington state road trip in character as a Starfleet crew and turned the result into a Star Trek-themed travel guide.

Remote and relaxed

Thanks to these strategies, I’ve had plenty of delightful, restorative holidays over the past two decades — even though my vacations have rarely removed me from my workplace. That’s good and the bad of working remotely; because your workplace is wherever you are, you never really leave it.

But that also means that your one can’t-miss meeting, your one demanding client, or your one unmissable deadline no longer has to keep you from taking the vacation you want. With a little bit of advanced planning and some honest self-appraisal of what makes you more or less relaxed, you can enjoy a vacation on the terms that work for you.