Why I Hate Vacations
Hey, it’s Andrew, Founder of Highrise and 2x founder. I previously sold my last business, eponym and was backed by investors like The Tisch Family, Sam Altman, Garry Tan (Initialized), Alexis Ohanian, RiverPark Ventures, and Tribeca Venture Partners.
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Read time: 3 Minutes
I hate the kind of vacations most people love. Beaches, resorts, cruises—they’re not for me. I like vacations to jump-start me, to jolt me into a new perspective, rather than sedate me.
Getting knocked off balance can be the best thing that happens to me. It forces me to notice things about myself that I might otherwise overlook. I’ve learned that the most meaningful lessons often come from moments of discomfort.
This happened right as we landed in Japan.
Even though it wasn't my first time in Japan or Narita Airport, I still felt that same disorienting impact. After customs, we were plunged into an arrival hall filled with a dizzying number of signs for trains, buses, and shuttles—most of them in Japanese. The signs blurred together, the sharp scent of unfamiliar air, the constant hum of announcements in another language, and the noise of bustling travelers filled my ears.
I felt the weight of not knowing where to go. Something I do without thinking in New York—navigating public transportation—suddenly became a new challenge. My heart raced as I paused, recalibrated, and tried to figure things out from scratch. It felt disorienting, but there was also a strange sense of excitement in it. It forced me to pay attention, to be fully present, and to let go of the routines I rely on at home.
Vacations, for me, aren’t about lying on a beach or going on a cruise. Those activities make me anxious—they feel stagnant, like I’m wasting time. In New York, about 80% of the places I go are ones I've been to many times before or a walk through Central Park. There's comfort in the familiar, in knowing what to expect.
But when I travel somewhere new, it's the opposite— at best, only 20% of the places are familiar, and the other 80% are there to surprise and stimulate me. I thrive in that kind of unpredictability, the sense that anything could happen and every moment is an opportunity to experience something for the first time. Real relaxation comes from being thrown into situations where I have to adapt and learn in real time.
The next day, we had lunch at a tempura restaurant that had been around for over a hundred years. It was a stark contrast to New York, where I’m used to sitting across from someone in a loud, energetic environment, waiting for the server to bring our food. Here, we sat side by side at a horseshoe-shaped counter, in near silence, accompanied only by our quiet conversation and the gentle sounds of the chef cooking in front of us. There were no distractions—just us, fully present in the moment.
The chef’s precision and deliberate preparation of each piece of tempura added to the atmosphere of intentionality. It wasn't just a meal; it was about being present. The quietness of the space, the focus on the moment, and watching the chef work were all refreshing contrasts to the hustle of New York.
You don't need to get on a 14-hour flight to reset. The question is: what does a true reset look like for you? What would push you out of your comfort zone enough to create real change?
It could be spending an uncomfortable amount of money on an experience, traveling far, or simply doing something that challenges you in a new way.
For me, only a part about this trip is about Japan specifically—it’s about disconnecting from the old and embracing the unknown.
It’s in that space—between what’s familiar and what’s different—that I find clarity.
While this trip is my current reset, I know that returning too often will eventually make it familiar, and I’ll need to find a new challenge to push myself further.
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