Why Can’t I Relax When I’m on Vacation?

Advice from The Sherwins for July 2019

Vacation FOMO


Hi Sherwins,

I’m going on holiday soon. Work has been unbelievably stressful (we launched two huge features in four months!) and I really need to just rest. 

The problem is that every time I go on holiday, I tend to freak out about trying to relax. Does that make sense? Do you have any advice?

C in London

Hey there, C! Congratulations on your well-earned vacation. And yes, freaking out about relaxing makes perfect sense.

There are some normal advice-y things you can do to make your holiday easier: Get some sleep, don’t party too much, don’t pressure yourself into seeing everything, eat regular meals, and don’t make radical adjustments to your normal schedule. Going from working 60-hour weeks to doing nothing in a single day will upset your mind and your body.

But let’s cut straight to it. You are not a machine. And it seems like we shouldn’t have to say it, but we do: You don’t just flip stress off like a lightswitch. Stress and anxiety, even happiness and love, these things take time. Time to build and grow, time to deconstruct and disassemble. Asking anyone to do this in a few days is ridiculous. And yet…

We do it all the time, especially through our products. We design things for notable gains over a short period of time. Sure, we have a few mechanisms lying about to track long-term actions, maybe when someone finally upgrades our product or unfollows our Medium posts. But for the most part, our power and profit is determined by short-term gains. If you aren’t 150% calmer by the end of Your Vacation™, then someone had better be selling their Tesla.

We are perfectly comfortable monetizing the immediacy of a behavior, the tap and release of endorphins. But behavior change is not a milestone. Despite our greatest hopes, people do not wake up one morning and become stress-free. They do not become kind or loving or fair overnight (they also don’t become horrible or racist). These changes are incremental and episodic, many of them requiring some amount of self-reflection around earlier patterns in their lives.

If you want this holiday to be different, and maybe start changing your future holidays, you should try the self-reflection path. Find one thing to think about. Set aside an hour and address it every day. Don’t set any goals other than that one hour, and handle it just like a researcher would. Say it’s that your retrospectives aren’t helping. Or that it takes too long to make decisions on your team. Maybe you feel like people aren’t respecting your time. Whatever it may be, ask yourself: What’s the problem and how do you recognize that it’s a problem? How do you benefit from this problem (there’s always a benefit), and can you achieve this benefit through other means? What concrete steps can you take to address this problem, when you get back from holiday?

We say “when you get back from holiday” because it will force you to think in the realities of your normal experience. Getting away from it all feels like fertile ground to change your life, but it’s a bit of a trap. Your normal experience is not being on holiday; it’s working. Don’t compound the pressure of change by expecting your hammock dreams to transfer to your standing desk.

We could say more, but really, go throw some clothes in a suitcase. That holiday isn’t happening without you.

All best,
The Sherwins

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Send questions to questions (at) askthesherwins (daht) com. All questions become the property of Ask The Sherwins, LLC and may be edited. Our advice shouldn't be construed as a replacement for the appropriate legal or professional counsel. This advice will be on vacation after July 31, 2019.