Vacations Are Important, but Most Founders Do Them Wrong

It felt like the exact wrong thing to do.

It was crazy.

Maybe even a little stupid.

We had recently finished our rebuilding project, trying to rescue our company from a slide into failure, and we were just starting to find our footing.

Things were going well, but after working our way out of the most turbulent period in our company’s history, things still felt fragile… 

And I was about to click “Book” on a 2-week vacation.

Part of me—the part powered by fear and self-doubt—was certain that this was a terrible idea, destined to result in nothing but an anxious, stressful vacation spent checking my phone at best, and a serious company setback at worst.

But another part of me—the one powered by years of advice and learning from mentors and more experienced entrepreneurs—knew that this was the right move.

And so I took the plunge, booking a trip to Block Island for two weeks of off-the-grid family time.

It turned out to be the smartest thing I could’ve done.

Going off the grid as a startup founder

As my wife, kids and I stepped onto the ferry that travels daily between Newport and Block Island in the summer, I took one last look at my inbox (I couldn’t resist), and then I deleted Gmail from my phone.

For two weeks, I went totally dark as far as Groove was concerned.

It was the first time I’d done this in nearly five years.

No phone calls, no email, no Slack, no social media, nothing.

I passed most of the time with my family: hanging out on the beach with my kids, conversations sitting outside with my wife, long dinners spent soaking in and enjoying the company of the people I love.

There was some alone time, too: I’ve gotten out of shape these last few years, and for the first time in a long time, I got back to exercising, running five miles each morning.

I can’t lie and say that I was never tempted to check in with our team. 

Old habits die hard, especially those built and cemented through years of stress and feedback loops that reinforce your fear of stepping away.

But those moments passed, and I got back to enjoying my trip.

The two weeks went by in the blink of an eye, and as I stepped off the return ferry in Newport, I was refreshed, energized and, aside from a bit of sunburn, feeling incredible.

And, of course, the company was just fine (more on that later).

But what I did next was perhaps the most important part of this post.

Here’s where the story might surprise you

Many founders have taken vacation before.

Plenty of workaholics in every role have done this before.

When you’re obsessed with your work, going on vacation might seem like a challenge to justify, but almost everyone ends up doing it.

But what I’ve realized is that it’s what happens after you return that determines how you’ll feel about taking vacations in the future.

Here’s what I mean: I’ve had many people tell me about their hard-won vacations, and how shocked they were that their company survived just fine without them, that they felt amazing, and that they were “ready to crush it” as soon as they got back.

Unfortunately, while I’m fully onboard with those first two insights, it’s the last one that I suspect is doing more harm than good.

At this point, it’s almost cliche to hear about how some high-achiever got back from vacation and closed 14 deals in a week, shipped a new feature in 3 days or did some other superhuman-sounding feat in a short period of time.

This is a mistake. 

And it’s one I’ve learned from—painfully—after past vacations.

I’ve hit the ground sprinting, only to drain my newly recharged batteries in a few short weeks and find myself back in my pre-vacation slump.

Vacation should serve to power your long-term work-life balance and sustainable level of productivity, not your short-term, post-vacation all-out sprints.

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And so instead of trying to work 18 hour days with my newly restored energy, I simply got back into my regular rhythm and routine.

It felt great, and I’ve been working at a high (but not strained) level of productivity that I’ll happily maintain…until my next vacation.

Vacation-ready companies are strong companies

While you might agree that taking vacations is important, you might also be scared to take one.

You might fear that, if you leave your business for an extended period of time, it’ll falter.

I was worried about the same thing, and in the past, it has kept me from taking many much-needed breaks.

But this time, it was crystal-clear when I returned that my absence hurt nothing…and I was thrilled.

It meant that all of the work we had been putting in to make the business less dependent on me had worked. 

Our new systems and processes meant that the business could run without me just fine.

The two key changes we made that allowed for this to happen are:

1. Adopting an Agile and organized approach to our roadmap, which means that projects have clear delivery dates, clear ownership and clear responsibility, rather than leaving everyone wondering who’s doing what and when things are getting done. When everything is laid out and documented this way, I don’t need to be there to push projects forward or put out fires.

2. Putting a true org chart in place, with leaders empowered to make decisions at the highest level, which meant that I didn’t need to be there to approve anything or settle any disagreements.

These improvements mean that any team member—not just me—can take a break from work without worrying about the entire operation backing up in their absence.

Take vacation time

When I was waffling between listening to the fear-and-doubt side of my brain and the reason-and-experience side, I was lucky that the latter won out and I ended up taking a much-needed vacation.

One of the most important factors in that decision was the countless pieces of advice I had gotten from other entrepreneurs who convinced me that a break would be useful, restorative and, if we built the right foundation, a net positive for our company.

Getting that permission from people I trusted was key in convincing myself to go, and I hope that this post gives you that permission, too.

If you’ve been denying yourself that vacation, you should go.

If your experience is like mine, you’ll be glad you did.