Redefining Success: How I Learned to Enjoy the Hamptons Without the Pressure

There’s an unspoken pressure that comes with success, isn’t there? Especially in a place like the Hamptons, where everyone seems to be competing in some invisible race. It’s a race you don’t even know you’ve signed up for, but suddenly you’re in it—keeping pace, climbing higher, never slowing down. You don’t question it because success looks like this, doesn’t it? You’re supposed to feel this pressure. You’re supposed to keep pushing.

I used to think that’s what success was: a series of accomplishments, a steady rise to the top, where the view from the summit is meant to be the reward. But somewhere along the way, I stopped looking at the view and started focusing on the climb. The endless, exhausting climb. And here’s the secret no one talks about: it’s never enough. No matter how high you climb, there’s always another peak in the distance, another goal just out of reach. You keep moving because slowing down feels like failure.

That’s how I ended up in the Hamptons every summer. Not just to relax, but to prove that I was still in the game. The dinners, the charity events, the social circuits—they all became part of this unspoken competition, this pressure to be seen as successful. And I was good at it. I knew how to perform, and how to keep up. But every summer, it felt a little heavier, like the weight of success was becoming too much to carry, never slowing down. You don’t question it because success looks like this, doesn’t it? You’re supposed to feel this pressure. You’re supposed to keep pushing.

It wasn’t until I found myself sitting on the edge of my perfectly manicured lawn, staring out at the ocean, that I realized I had been chasing a version of success that didn’t belong to me. The pressure had been building for years, but I hadn’t stopped long enough to notice it. Until that day. I sat there, watching the waves roll in and out, and felt this strange emptiness. I had everything I thought I wanted, but none of it felt real.

In Radical Acceptance by Tara Brach, she writes about how we get trapped in the endless pursuit of achievement, always striving, never satisfied. Brach talks about the feeling of being caught in “the trance of unworthiness”—a state where no matter how much we achieve, it never feels like enough because we don’t believe we’re enough. That resonated with me. I had been chasing success for so long, I hadn’t realized that it wasn’t the external achievements I was seeking. It was validation.

I was playing a game I didn’t even want to win.

The Moment I Stopped Playing

That summer, something shifted. It wasn’t dramatic—there was no grand decision to quit or run away. It was subtler than that. I simply... stopped. I stopped pushing, stopped trying to keep up, stopped chasing this invisible ideal of success. I decided that maybe the problem wasn’t with the summit. Maybe the problem was with the climb itself.

The next day, I skipped a charity gala I had RSVP’d to months ago. Instead of spending the evening in a crowded ballroom, smiling for pictures and making small talk, I spent it by the ocean, alone. I watched the sunset, the sky turning from pink to orange to deep indigo. And in that quiet, I realized that this—this stillness—was what I had been missing. Not the events, not the accolades, but the simple, quiet moments where I didn’t have to prove anything to anyone.

In The Art of Happiness, the Dalai Lama writes that true happiness doesn’t come from success or wealth, but from inner peace, from the ability to be content with where you are and who you are. I had spent so much time focusing on what was next that I had forgotten how to be content with where I was. The Hamptons had always been a place of more—more status, more success, more pressure. But that night, it became a place of less. Less expectation. Less pressure. Less performance.

Redefining What Success Means

That summer, I began to rethink what success looked like for me. It wasn’t about being at every event, shaking the right hands, or being seen in the right places. It was about slowing down, about finding moments of joy and peace in the simplest things. A quiet walk in the early morning before the town woke up. A long conversation with a close friend that wasn’t about business or networking. An afternoon spent reading in the sun without the pressure of the world demanding my attention.

The more I let go of the pressure, the more I realized that success wasn’t something I needed to prove to anyone. Success wasn’t in the external achievements—it was in how I felt about my life, how present I was in the moments that mattered.

The Myth of Success by Karina Medici talks about this idea of redefining success on your own terms. She writes that success, as we’ve been taught to see it, is an illusion—a moving target that we’ll never quite reach because the goalposts keep shifting. Real success, Medici argues, is about living in alignment with your values, with what truly matters to you, not what the world tells you should matter.

For the first time in years, I started to feel like I was living for myself, not for the expectations of others. And the pressure? It started to lift.

Finding Joy Without the Pressure

I began to embrace the slower pace of the Hamptons, not as a place to perform but as a place to retreat, to reconnect with myself. I stopped worrying about whether I was doing enough, whether I was being enough. I started to enjoy the moments that felt insignificant to the outside world but meant everything to me—quiet dinners with close friends, spontaneous walks along the beach, afternoons spent watching the clouds pass by.

I learned that the pressure to succeed was self-imposed, born out of the fear that if I slowed down, I’d somehow fall behind. But the truth is, there’s nothing to fall behind on when you’re living life on your own terms. The Hamptons, with all its expectations and social performance, had taught me one thing: the only person whose definition of success matters is my own.

Takeaways to Share

So here’s the question I want to ask you: What version of success are you chasing? And is it even your own? What would happen if you let go of the pressure to keep climbing and started enjoying the view from where you are?

Here’s what I’ve learned:

• Success isn’t something you prove to others. It’s something you feel when you’re living in alignment with your own values.
• The pressure to achieve more is never-ending. True success comes from knowing when to stop and appreciate what you’ve already accomplished.
• Happiness isn’t found at the summit. It’s found in the quiet moments along the way.

Join the Conversation

What’s one way you can redefine success for yourself? What’s one pressure you can let go of this week? Share your thoughts in the comments or tag someone who might need a reminder to enjoy the journey instead of constantly chasing the next goal.

Here’s the quote that changed everything for me: "Success is not about getting more, it’s about being more—more present, more content, more yourself." — Tara Brach Share this with someone who might need a reminder that real success comes from within.

Call to Action: What’s one way you can redefine success on your own terms this week? How can you let go of the pressure and enjoy the life you’ve built? Share your thoughts below, or pass this along to someone who might need encouragement to slow down and enjoy the moment.