“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do.” ~Mark Twain
Let me set the scene.
It’s a blistering summer day in Miami—the kind where the humidity hugs you tighter than your ex at a high school reunion, and the air feels like you’re swimming through warm soup. Not exactly the kind of weather that makes you want to move, let alone sweat through a surprise death-match workout on Muscle Beach.
But there I was.
The trainer—clearly a drill sergeant in a past life—barks out: “One more rep and we’re done!”
Ah, yes. The famous last words of every group fitness class ever.
Spoiler: We were not done.
That “one more rep” turned into ten more exercises, each more punishing than the last. By the end, I was convinced my legs had filed for emancipation. My tank top could’ve been used to mop the floor. And yet… beneath the exhaustion was a wild, inexplicable sense of aliveness.
As we collapsed onto the grass post-torture, I tilted my head to the sky—not for inspiration, but perhaps divine rescue. Instead, I got clouds. Big, moody ones, rolling in fast.
Now, as a Miami local, I knew what was coming. Rain. In five minutes, give or take.
Our group—equal parts sweaty and semi-traumatized—decided to grab food at a nearby Greek spot six blocks away. It would’ve been an easy call… if the weather weren’t about to turn into a tropical tantrum.
And that’s when the debate began: “To Uber or not to Uber?”
That was the moment.
That was the question that cracked open something bigger than I expected.
Because I found myself thinking—not practically, but existentially: What would make the better story?
Ubering dry and comfortable? Or walking into the storm, drenched and laughing?
You can guess which one I chose.
We set off on foot.
The first raindrops were tentative, almost polite. Then came the downpour. The real deal. Within moments, we were soaked to the skin—but free.
We splashed through puddles. We screamed. We laughed like kids who were allowed to stay up past bedtime.
When we finally burst into the restaurant—sopping wet, windswept, and grinning—we looked like a group of joyful chaos incarnate. No one cared about how they looked. No one regretted the walk.
Because we didn’t just choose a meal. We chose a memory.
So now I’ll ask you the same thing I asked myself: What would make the better story?
Not the easier one. Not the polished one. Not the one that keeps you neat and unbothered.
The better story. The one with heart and risk and color. The one where you come alive—even if you get a little messy in the process.
We tend to make choices based on comfort or control. We pick what’s convenient. Predictable. Safe. But the stories we remember—and the ones we’re proud to tell—usually start with a moment of uncertainty.
A leap. A yes. A “Why not?”
Maybe it’s the relationship that felt like a risk but turned into something real.
Maybe it’s the day you finally stood up for yourself, even though your voice trembled.
Maybe it’s the job you didn’t feel ready for but said yes to anyway.
Or maybe, like me, it’s just a walk in the rain that reminded you how alive you really are.
Your life is made up of stories.
And every day, you’re writing the next line.
So what will it be today? Will you play it safe? Or will you choose the version of this day—the version of yourself—that you’ll be proud to look back on?
About Danielle Dam
Danielle Dam is a life and leadership coach, speaker, and founder of Coach Dam LLC. Through her signature program, From Unseen to Unforgettable (U2U), she helps ambitious yet overwhelmed women stop living on autopilot and start leading lives that actually feel as good as they look. After years of chasing external validation, Danielle now empowers others to reconnect with their truth, rewrite old patterns, and build a life rooted in purpose, presence, and personal power. Learn more or connect with her at coachdam.com or on Instagram @Danielle_coachdam.
