Failure #6: You’re Allowed to Rest

Shhhh… I’m on vacation.

Just don’t tell anyone. I wouldn’t want people thinking I don’t work hard.

It’s a ridiculous instinct, I know. And yet, I can’t seem to help myself. Every time I open my laptop for a few “quick emails,” I feel a little burst of pride, like I’ve proven I’m still committed. And every time I don’t, I feel a little whisper of guilt, as if I’ve done something wrong.

I bring this up because I know I’m not alone. Most adults I know are terrible at taking vacation. And I don’t mean logistically — I mean psychologically. The moment we try to unplug, we simultaneously start to unravel as our brains race through some combination of what we’re missing and what our absence is signaling. Our Slack pings haunt us as our ambition turns into a security blanket we can’t put down. And our insecurity turns into a pair of handcuffs that keep us checking our phones “just in case.”

The problem isn’t that we work too much or have unhealthy relationships with our jobs.

Our problem is that school trained us to feel like “time off” has a consequence rather than a benefit.

Summer Wasn’t a Break. It Was a Countdown.

Think about your earliest experiences with going on vacation. You weren’t some middle manager using your PTO. You were a kid going on “summer vacation.” But was it really a vacation? You surely didn’t have the autonomy to relax. You were scheduled for camp. Or for your grandparents to watch you. Or a summer job. Even worse, the “break” always came with a rigid timeline and  looming return to obligation. You had three months. Or ten weeks. Or 72 days. At the end of that countdown was the hard work and drudgery of another school year.

As you got older, you got summer homework, too. A reading log. A math packet. Something to make sure your brain stayed “productive.” Heaven forbid a child learn that being bored is actually healthy.

Even when there wasn’t homework, we all got the same message: summer vacation has a clear end, and when it ends, you’d better be ready to prove you didn’t fall behind.

Is that really a break? Or is it an intermission with severe consequences for people who struggle with self-motivation?

Vacation, Rebranded for Instagram

Fast forward a few decades from those grade school summer breaks, and the stakes have only gotten higher. Now when we go on vacation, it’s not just time off — it’s a statement. A luxury. A flex. Something to post. Something to compare. We can’t just go on a trip. We have to go on a trip that’s going to show how our lives compare with the lives of all the other people in our social circles.

And while we’re flaunting our disposable income to one group of people in our lives, we also feel obligated to justify the break to another group of people: the ones we work with.

We make sure we’re reachable. We check our email “just in case.” We over-apologize to coworkers before we leave.

Plus, on top of everything else, a vacation can’t just be time to relax. It has to live up to some ‘gram-worthy version of what vacations are supposed to look like, which means we have to over-plan our itineraries and make sure every second of our “break” is maximized.

In short: we’ve turned vacations into more work than skipping the vacation and just going to work. Then we wonder why we’re exhausted when we get back.

Somewhere along the way, we absorbed the idea that our value comes from how relentlessly we can produce. Even our rest must be productive. Even our escape must be scheduled.

We don't rest. We perform rest.

The Lesson About Vacations School Forgot to Teach

School taught us how to work hard. But it didn’t teach us how to recover.

It didn’t teach us how to step away from something without guilt. It didn’t teach us how to say, “That’s enough for today.” It didn’t teach us how to decouple our worth from our output. If anything, it taught us the exact opposite. It taught us to work hard, spend more time, do more, add more to the college application because the harder we work, the more we’ll achieve.

And while working hard is important and valuable, the corollary of that statement isn’t that rest is a form of laziness. Despite what school taught you, idleness isn’t failure. In fact, rest isn’t the opposite of success. It’s a critical part of it.

The ability to rest well is a skill. It’s something you have to practice — especially in an age where rest and vacation have become so performative.

Heck, here I am, performing for all of you. I’m on vacation, but I’m still sending out my newsletter, and I’m still posting my videos, and I’m still responding to emails. By doing those things, I’m telling anyone who sees those things that “successful people never stop working.”

Sorry! I’m part of the problem.

So let me do my part to fix the problem. This newsletter you’re reading wasn’t written while I’m on vacation. It was written three weeks before and scheduled to get delivered today.

The same is true with my videos. Even if you see something I’ve posted in the past week, I’m not actually posting. I intentionally filmed extra videos in the weeks leading up to my trip and scheduled them to post while I’m away.

In other words, the non-stop Dr. Dinin you’re reading right now, who’s still in his classroom even when his students aren’t… yeah… he’s actually sipping a fruity drink on a beach somewhere. And this newsletter is part of a carefully crafted illusion to make sure Dr. Dinin “keeps working” even though Aaron Dinin, the human behind the newsletters, articles, and videos takes a much needed break.

I’m pulling back this piece of the proverbial curtain in order to remind anyone reading this that the things you’re seeing and comparing yourself to… they’re probably not as real as you think. That picture of your friends in Rome smiling in front of the Coliseum was snapped during the only 30 minutes of the entire vacation when it wasn’t pouring. That cruise you’re watching your co-worker take for a week is actually because she’s got a big stash of vacation days that are going to expire if she doesn’t use them.

And maybe — just maybe — stepping away from everything in your life for a week won’t cause you to fall behind. Maybe it’ll be the only way you ever catch up.

-Dr. D