Regret is a trap. It tricks us into looking backward instead of forward, replaying past decisions as if we can go back and rewrite them. But regret changes nothing—it’s just wasted energy.
At the same time, when people reflect on their lives, they don’t wish they had played it safer. They wish they had taken more chances. Not because risk-taking guarantees success, but because it means they truly lived.
Jerry Seinfeld’s Take on Meditations
Jerry Seinfeld recently shared his biggest takeaway from Meditations by Marcus Aurelius:
All the things we worry about—people’s opinions, criticism, missed opportunities—will be gone in a blink. The people judging you? They’ll be gone. The situations you’re stressing over? They’ll fade away. Even you won’t be here forever.
So why waste time on what doesn’t matter?
What Does Matter?
We waste so much energy worrying—about what others think, about what we should have done differently, about how we’re being perceived. But none of that changes anything. The past is over. Regret won’t fix it.
What actually matters? Getting better at what you do. Focusing on the work, the relationships, and the purpose that actually make a difference. Moving forward instead of looking back.
Stoicism teaches that the best way to avoid future regret is to take action now. The risks we avoided yesterday don’t matter anymore. The real question is:
What are we avoiding today?
What bold move are we hesitating to make?
Playing It Safe Won’t Save You
Too many people think avoiding risk will protect them. They think staying comfortable is the smart play. But what if the real danger is the slow erosion of your potential?
Fear of failure keeps people stuck. But real security—the kind that lasts—comes from building the strength to handle whatever comes next.
Because in the end, courage isn’t the absence of fear. It’s acting in spite of it.
You Still Have Time—Use It
You don’t need to regret the chances you didn’t take—you can start taking them now. The clock is running, and everything you’re afraid of today will eventually disappear.
So stop looking backward. Move forward. Take the risk. Do the thing.
The biggest risk isn’t failing. It’s never trying at all.
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