How to Take Restorative Time Off While Working at a Startup

April 23, 2024
March 2, 2021
| Updated
January 19, 2023
The Distru Team (Dec 2020)
The Distru Team (Dec 2020)

As a startup founder or an early employee, taking vacations seems counterintuitive. The infamous “Unlimited PTO” usually means you take little to none, and when you finally do get the chance to, you end up playing backlog catchup anyways.

Over the past 4 years of building Distru, I’ve taken 4 week-long vacations as a founder (this is not enough, more on this later). Although it was a hard commitment to make each time, taking those week-long vacations had the most impact on myself and the company each time.

Misguided Guilt & Accountability

Everyone at Distru feels a great deal of accountability towards each other. We constantly step up and understand that we are responsible for the successes of ourselves and our teammates.

The downside to this culture of accountability is misguided guilt at the thought of taking time off. This manifests for me in the form of a story I constantly tell myself:

"Look at how hard everyone else is working, I can’t take a week off!”

I am only now starting to realize how counterproductive this mindset is for our work culture. By not allowing myself to take breaks and heal, I was unconsciously signaling to others that they should do the same (which was the furthest from the truth). I had inadvertently contributed to creating an unsustainable culture of endless high octane performance. A culture that drove me into the ground multiple times, and would do the same to others if I allowed it to.

So the question I had to ask myself was: “Is taking a week off for myself so bad that I’m willing to burn out my team and potentially lose them over it?”.

When you reframe vacations from this lens, taking time off suddenly feels like a pretty high leverage thing for you (and everyone else in the company) to do regularly.

The Goal is to Recharge, Not to Improve

Once I got past the guilt of taking time for myself, I still had a lingering thought in the back of my mind: “What if I don’t come back better? What if I’m still tired and burnt-out?”.

A good vacation’s goal is to recharge the body & mind. It can feel tempting to want to come back from your vacation a better version of yourself, to have improved somehow. But by setting those expectations, you are adding unnecessary pressure to a process that is supposed to relieve pressure, and robbing yourself of the true reason you needed the vacation, to begin with.

As biological creatures, we are constantly oscillating between energy expenditure and energy replenishment. It’s very easy to imbalance the two in a fast-paced start-up full of high-performing motivated individuals. But there’s a reason why we can’t live without sleeping, we need to recharge. This applies to work; recharging your body and mind and encouraging others to do the same results in higher and more efficient productivity over time, as well as personal wellbeing which should always be the priority.

Don’t fester over improving yourself, or even being fully recharged. Those things happen naturally when you let go of expectations and allow yourself to be.

How to Safely Unplug

One of the most powerful ways to recharge during your vacation is to unplug yourself fully from work. This is incredibly hard as we carry our work on our computers, our phones, and with us in our minds.

The intention to unplug alone will not help you truly unplug. To truly unplug requires a level of psychological safety in doing so, in knowing that it will not come back to bite you harder later on. At Distru, we’ve found some ways to maximize the psychological safety that’s needed in order to unplug safely:

  • Pick a co-worker that has the context to be your fallback while you’re gone
  • Set up your vacation responder to recommend contacting your fallback co-worker instead of texting/calling you directly for emergencies
  • Ask everyone who works closely with you to build you a “Back In Office” list of things that you need to take action on when you get back
  • Ask an admin to lock you out of your Slack and Email accounts entirely

The purpose of this list is to cover your bases as much as possible, so your mind is not in “Did I turn the stove off?” mode. The best way to safely unplug is to make sure the stove itself is unplugged 😉.

PS: This is by no means a full list (or even the best list). If you have tactics you’d like to share with me, please let me know —!

Distru’s Vacation Strategy

I mentioned earlier in this article that as a founder, I took 4 vacations over 4 years. I’ve come to recognize over time that this is not nearly enough. Furthermore, how could I myself preach that my team should take more time off to restore when I don’t set an example myself?

Distru is committed to building the highest functioning team over a sustained period of time. In order to do so, our vacation strategy has to account for continuous restoration and healing. We still have a long way to go as a company to perfect this, but we are moving in the right direction with each passing day.

In closing, I’d like to share a couple of things that Distru does today to help us become a more sustainably functioning company. I hope that others who aspire to achieve the same can find this useful in some way!

3 Weeks of Vacation per Year

“Unlimited PTO” is hard to keep track of, and harder to enforce. By putting a number on the amount of vacation time every team member gets, you can enforce this easily throughout the year. The 3-week number is not important, but a number is.

Vacation Reminders via Check-Ins

For some of the reasons outlined in this article (and many others), people tend to forget to take time off if you don’t remind them. We’ve found the best way is to remind people through natural check-ins. These include:

  • 1:1s as a manager, help your direct reports plan time off if you notice it’s been a while since their last vacation
  • People Ops ask your People Operations/HR department to track time off and ensure no one goes too long without taking a vacation
  • Company Meetings remind your team to take time off whenever you get the chance (all hands, OKR planning sessions etc…)

If you have more to add to this topic, please reach out to me via We’re always trying to learn and improve as a company, and any thought exchange in that effort is greatly appreciated!

Lastly, Distru is currently hiring for product-minded engineers that want to build software powering the future of the Cannabis supply-chain. If you’re interested in learning more, please reach out via our careers page and I’d be happy to jump on a call with you!

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