How Can You Take Vacations And Work Hard As A Startup CEO?

Empty hammock between palm trees on tropical beach

I’ll never forget being at a CEO conference organized by one of our investors. One of the speakers was an extremely famous CEO.

The CEO was rambling on and on. Then, out of nowhere, he said, “I work 16 hours a day, seven days a week.”

My head snapped straight up. I wanted to scream, “I call BS!” But, that refrain had not been invented yet.

A few weeks later pictures emerged of the famous CEO and his girlfriend cavorting in Japan. I guess even alleged 16 hour a day, 7 days a week workaholics take vacations…

As for me, I worked hard. Really hard. But I always regularly took vacations.


And I encouraged everyone on our team to take vacations too.

I needed the breaks and the downtime to give me the energy to keep driving forwards. But having said that, my brain was always thinking about the company.


And I always felt guilty every time I took a vacation.


I knew it was good for me to take time off. But I always felt this incredible amount of guilt. I’d say to myself, “Shouldn’t I be at the office?” Or I’d wonder, “Am I setting a bad example by taking a vacation?”

Then I’d remember the saying, “Startups are marathons, not sprints.”

You need to take vacations because you’re going to be grinding for the next seven to ten years. Try doing that 16 hours a day, 7 days a week... FOR SEVEN TO TEN YEARS!


But you’re never truly on vacation when you’re a CEO.


We took some great and memorable vacations when I was CEO. But I still thinking about work. And sometimes I would have to call into the office because of various meetings and problems that were happening.

That’s just part of the deal of being CEO.

So maybe the famous CEO wasn’t lying. Maybe what he really meant to say was that even when he wasn’t officially working, his brain was still trying to solve work-related problems.

That would ring with a little more truth to me.

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