What Works

What Works


Taking A Break From Business: What I Wish Every Entrepreneur Knew

July 01, 2021

Do you ever get the feeling you’re white-knuckling it through business ownership?

Like if you just squeeze the wheel hard enough and focus on what’s in front of you, you can keep your business from ending up in a serious fender bender (or worse)?

I’ve certainly felt that way. All throughout 2020, I felt like my extreme vigilance was the only thing between my business and an 8-car pileup. And we didn’t get hit nearly as hard as many businesses.

It’s a burden, being able to control situations with my hyper-vigilance, but it’s my lot in life. — Tina Fey, Bossypants

That hyper-vigilance can look like needing to have my fingers in every project or having to touch base with every customer. It can look like working 10 hours a day or checking in on the weekends. It can look like not going on vacation for fear of things crumbling without me or always leaving my inbox open throughout the day.

This last year involved every one of those habits at one point or another. Sometimes all at once.

Truthfully, I’m still burnt out from The Year Of White-Knuckling.

And I need a break. That’s why, if you’re reading this at the time it’s published, I’m unplugged and on vacation. Note from writing self to vacation self: seriously, let go—don’t work this week.

Of course, “taking a break” isn’t just about taking a vacation. It might mean making space for a creative project. Or making time to work on your business. Or taking Fridays off. Or putting your podcast on hiatus. There are so many ways to take a break from things that drain us (even if we love them) but hyper-vigilance is not the way you do it.

Last year notwithstanding, I’ve led my business to a pretty peaceful equilibrium.

We have strong systems, predictable cycles of work, and a dreamy community of customers who cheer when we take some time off.

But I also catch a glimpse of my former hyper-vigilant self every time I see Sean worry about our clients on the weekends or try to make vacation plans around reliable access to the internet every morning.

While it would be wonderful to work in a world where taking a break meant just shutting down the computer on a Friday with no preparation and not giving work a second thought for 10 days, taking a break takes some work.

There is work to be done on the business—I’ll get to the specifics in just a moment—and there is also mental work.

Now, if you’re not the anxious, hyper-vigilant business owner that I am, maybe mentally preparing for a break isn’t so hard. I have no idea what that’s like. Feel free to skip ahead, though.

For all the worriers out there, probably the most helpful mental shift I’ve made over the years is learning that:

There is no amount of worry or hyper-vigilance that will stop something bad from happening.

I can’t not take a break because I believe checking email every day averts all potential problems.

Ish happens.

Even the best systems, happiest customers, and most independent team members won’t stop the random problem from breaking through.

But just because I can’t stop a problem from happening doesn’t mean that a problem will happen. I can take a few days or a few weeks off without there being a problem that...