Let’s talk about taking time off

For many people, vacation is chicken soup for the soul. However, during my professional career, taking vacation has always led to a series of guilt trips. As a result, I have developed an unhealthy relationship with taking time off. This has a negative effect on me, my family and my co-workers.

I love what I do and I Iove the work. However, that love can translate into an obsession and a fixation to keep working even thought I should be getting some occasional distance form work.

This post explores a couple of turning points, both personal and professional, that changed how I feel about taking time off and has made me start to enjoy vacation for the first time since childhood.

How it started

In my first job as a lowly investment banking analyst in New York City, I could barely get any time off. Even after working nights and weekends for the first six months straight, I could only get 2 business days off to go home to see my family on the other side of the country in San Francisco for Thanksgiving.

Another formidable experience came when my wife and I were expecting our first child. We took a week off to go on a babymoon and a month later I was fired.

These work experiences were foundational professional moments that made me equate time off with something nefarious.

Startup life

As an entrepreneur, any day not working was a day that I wasn’t building. Taking time off is the ultimate offense in hustle culture. The feeling of needing some time off, but not being able to take it is like a chicken running with its head cut off: a chaotic frenzy.

Even as the CEO of Dutch, I’ve felt guilty about taking time off. I remember how this all came to a head. I had taken my first vacation of just a few days (by the way, I don’t think I’ve ever taken off more then 10 business days off at a time). I was with my family on a wonderful trip in London and staying at a wonderful hotel, but I kept staying up to work and being super stressed out. After several days of this, when we were out to eat at a fancy restaurant with our kids, my wife said to me, “If you can’t be happy here, maybe you can’t be happy anywhere.”

With that, something clicked for me. The first thing I did is to close my laptop. I also deleted apps like Shopify for my phone so that I’m not able to check our sales every few minutes and stress about each hour’s sales. I also moved the email app off my main screen and onto the last page of apps. I deleted all social media apps from my phone including LinkedIn – that was a hard one for me as a power user.

Even though there were only few days left during that vacation, I was able to enjoy London. It’s one of my favorite cities.

At work

As much as I’ve had a challenging relationship with vacation and time off for myself, it has been a challenge as the employer as well. At Dutch, we have an unlimited vacation policy. There are people who take six weeks off work and there are those who take off one week. The range is quite significant. Prior to being a founder, I would read about unlimited time off policies and how they get abused, but now I’ve seen it firsthand. As you can imagine, this discomfort led to feelings of frustration within myself and resulted in some tough conversations that I’m sure were even more frustrating for others.

I used to think that there’s a correlation between those who were outstanding achievers with time off. That’s not necessarily what I have learned. Maybe it’s obvious to others, but I realized when great workers took time off to recharge, they were able to create the distance needed to better think about the big picture of our business. Again, this sounds like simple math, but it’s not to a workaholic.

Final thoughts

I’m still at a work in progress stage on this, but I’m certainly not turning back. This week my cousin is getting married in Italy and even though I’m only taking four days off (I did say I’m a work in progress), I plan to fully enjoy the moment. On the professional side, my aim is to trust my employees and make them feel safe and excited to take the time off they need knowing that my judgement of their abilities will come from the results they achieve rather than how much or how little time off they took.