The Fort

The Monday blog · August 24, 2026

I'm terrible at vacations

By Dan Trink, co-founder of The Fort · 4 min read

We just got back.

Five days and four nights on the New England coastline.

We’ve been doing some version of this trip nearly every Summer for the past 14 years.

My wife enjoys it because 1) she enjoys getting away and 2) it reminds her of her summers growing up near these same shoreline towns. My son enjoys it because he 1) enjoys getting away and 2) he likes the aquarium and going to the beach and, I realize this seems biased, just spending time with us.

Most people spend their entire year awaiting vacation. They can’t wait to go and lament coming back.

I, on the other hand, struggle. As the title of this blog suggests, I am terrible at vacations.

Before you “at me” as the kids say, yes, I understand the value of getting away. Of breaking the routine, relaxing and getting a fresh perspective. I can intellectualize the need for balance and new stimulation.

And it’s not that I don’t enjoy myself, I do. I’m not opposed to having an ocean breeze on my scalp or seeing a trained seal waive its tail on command or eating some fish tacos. And I do appreciate uninterrupted time with my family. It’s good for them and it’s good for me.

Yet I spend a lot of the time secretly wanting to go home. By day two I’m planning out new guitar lessons. By day three I’m pricing completely unnecessary fitness equipment.

The food I like to eat is at home. The gym is at home. So are my friends and co-workers.

I can work on the new program at home. I can also sit on the couch and play guitar for 15 minutes. Or catch an episode of The Bear with my wife. Or head outside to my preferred running route. Or take my son to our complex’s heated pool (why are indoor hotel pools so cold???).

And this all begs the question “what is wrong with me?” Why do I prefer the struggles, the routines, the people and the monotony that everyone else is trying to escape? Cause I’m certain my co-workers aren’t thinking “I wonder what Dan is up to” when they are in Miami Beach for the weekend.

I’ve thought about this quite a bit (mostly while on vacation) and I’ve come up with two potential answers.

The first is that I have some mental health issue.

That I rely on the ability to take action and be surrounded by the things I can control and are familiar to me in order to stave off the anxiety of being a small business owner, Dad to a special needs son, husband, son, brother and desperately-wanting-to-be-a-valuable citizen of the world.

And vacations take me away from all that.

I’d say there is a decent chance that’s it.

The more optimistic possibility is that I’ve simply - unlike many, many people - created a life that I truly enjoy. And escaping it feels like a downgrade.

I love getting to workout with my training partners. I enjoy getting to the end of the day and knowing that I’ve eaten for my goals and not who-the-fuck-knows-what-they-put-in-it restaurant food. I revel in coming up with a personal, ten minute story that circuitously leads to some point I am trying to make to my leadership team to start off our Monday meetings (although, to be fair, I’m not so sure how much they enjoy that). I enjoy methodically working on the same seven note guitar passage for 30 minutes until I get it under my fingers.

Which, perhaps, leads me to this lovely conclusion. Maybe I’ve simply been lucky enough to build a life I enjoy and days I look forward to. I’m terrible at vacations because I’ve managed to create a daily life I love, even with all its challenges and commutes and worries and everything else that are admittedly a part of it.

It’s sad for me to think that some people only feel alive when they are on vacation. That their days are simply a series of survival tasks until they’ve saved up enough money and PTO to go to the Grand Canyon for two weeks and finally breathe.

Hopefully that’s not you. Hopefully, you enjoy both. Perhaps you just like to travel. See new cultures. Or experience the wonders of the world. The Grand Canyon is beautiful. I’ve been there on vacation.

But, if that isn’t you. If you are living your life for two weeks per year I have some straight-on-the-nose advice for you, do something about it. Love your life or change it.

August is coming to an end and we are about to approach what I call “New York New Year”. That time when everyone comes off the beach and back from Long Island and floods the City. And this is the perfect time to restart building the life and routines you enjoy.

Enroll in a pottery class or start a weekly card game with friends or, I don’t know, join a gym and go three times per week. Try to build something that you’ll actually miss next July when you head out of town.

You don’t need to be terrible at vacations. But maybe you can be better at everything else that surrounds them.

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