A few nights ago, I finished Replay by Ken Grimwood. Then I just… sat there. Not scrolling. Not thinking. Just staring at the wall, quietly overwhelmed. I wasn’t sad. I wasn’t inspired. I was suspended, replaying my own life in fragments.
The premise is deceptively simple: Jeff Winston dies of a heart attack at 43… and wakes up in his 18-year-old body. Fully aware. Memory intact. Again. And again. Each time, he lives a different version of his life, hoping to finally get it “right.”
But what unfolds isn’t wish fulfillment. It’s a study in regret. In restlessness. In the unbearable weight of endless do-overs. He has money. He has fame. He can change the world, or walk away from it entirely. Still, none of it gives him what he thought he wanted.
That story stayed with me, not because it was dramatic, but because it made me ask:
If I had to live my life a hundred times… What would I still want to be true?
The Choices That Still Feel Right on the Hundredth Loop
Jeff tries everything. Riches. Romance. Power. Detachment. Religion. Hedonism. Each path seems promising… until it doesn’t. He builds empires, lives simply, and even gives up. But no matter the version, he always ends up with the same question: Why does this still feel empty?
Eventually, something shifts. The thrill-seeking quiets. He stops optimizing and starts observing. He lets go of the idea that there’s a perfect version of his life out there, waiting to be discovered like some buried treasure.
He starts paying attention to the choices that don’t glitter, but still feel good when everything else fades. Certain moments begin to hold up: a genuine conversation. The feeling of showing up for someone. Choosing what matters, even when no one notices.
These are the moments that start to outlast every reset.
It made me stop and ask:
- What feels right even when no one’s watching?
- What version of myself am I reinforcing right now?
- What have I chosen not just once, but again and again?
There are things I thought I wanted five years ago that no longer speak to me at all. But there are also choices I return to without hesitation: small habits, deep relationships, creative projects that ask something of me and give something back.
I remember one weekend when I said yes to three separate commitments out of guilt. Brunch with someone I hadn’t seen in ages, a Zoom catch-up I didn’t have energy for, and a birthday party I’d signed up for weeks earlier.
By Sunday night, I was drained, not from doing too much, but from doing too much of what didn’t feel like mine. That’s when it clicked: if I had to relive that weekend a hundred times, I’d leave it behind every time.
That shift didn’t come from a grand insight. Just a quiet one. Some choices are exciting only once. But others feel like home, no matter how often you return to them.
You Don’t Need a Do-Over. You Need a Pause
None of us can relive our lives from the beginning. But we don’t need to. All it takes is a pause. A breath. A moment to notice before you move. These moments pass quickly unless you catch them.
So, before the next yes, the next scroll, the next habit on autopilot, ask:
- Would I choose this again?
- Would future-me repeat it, or quietly change the channel?
Here’s how that might look:
- You’re about to agree to a coffee meeting you’re dreading. Pause. Consider: If I lived today a hundred times, would I want this to be part of it?
- You’re scrolling at midnight. Again. Ask: Would I want to feel like this version of myself on repeat?
- You’re debating a career shift. Instead of Is this a smart move? Try: Would I be proud to live this version of my work again and again?
When something feels urgent, pause. Write it down. Step away. If it still feels right after a bit of space, that’s a sign it’ll hold up. Of course, we can’t predict what will still matter a decade from now.
But we almost always know what already feels hollow. And that’s enough to choose differently today. No, you won’t always know what future-you will cherish. But if something already feels like a stretch to justify, it probably won’t age well on the replay.
Live Like You’d Want to Watch It Again
So, what do you do with that kind of clarity? You don’t need a master plan. You don’t need to be perfect. You just need to start noticing what you’d never want to un-choose.
The most meaningful moments—the ones that hold up in the replay—usually aren’t flashy. They’re the slow walks, the quiet honesty, the work that feels worth doing even when no one’s looking.
So, when you find yourself chasing something, it helps to ask:
- Is this a life I’d want to keep watching unfold?
- Or am I just hoping this version will finally earn the applause I’ve been waiting for?
What kind of person are you becoming, on repeat?
Don’t build a life that looks good once. Build one that feels right again and again. The truest choices—the ones that still matter after the rush fades—aren’t the ones that impress the world. They’re the ones you’d keep making, even if no one ever saw them.
Jeff Winston lives the truth most of us never get to test:
Some choices only get clearer with each return.
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