Moments
When I was in my early 20s, I stumbled upon a poem that fundamentally changed my perspective on life. It was written by an elderly woman reflecting on her experiences, titled “If I Had to Live My Life Over Again.”
“If I had my life to live over, I’d dare to make more mistakes next time. I’d relax, I would limber up. I would be sillier than I have been this trip. I would take fewer things seriously. I would take more chances. I would climb more mountains and swim more rivers. I would eat more ice cream and less beans. I would perhaps have more actual troubles, but I’d have fewer imaginary ones.
You see, I’m one of those people who lived sensibly and sanely, hour after hour, day after day. Oh, I’ve had my moments, and if I had to do it over again, I’d have more of them. In fact, I’d try to have nothing else. Just moments, one after another, instead of living so many years ahead of each day. I’ve been one of those persons who never goes anywhere without a thermometer, a hot water bottle, a raincoat and a parachute. If I had to do it again, I would travel lighter than I have.
If I had my life to live over, I would start barefoot earlier in the spring and stay that way later in the fall. I would go to more dances. I would ride more merry-go-rounds. I would pick more daisies.”
At first glance, her words seem deceptively simple: Live life fully. Take risks. Seek moments of joy. But isn’t that what everyone wants? The truth is, most people say they crave adventure but cling to the comfort of routine. I’ve lost count of how often I hear, “I’m so envious of your life” or “Wow, I wish I could travel like you do.” My response is always the same: “Don’t be envious or jealous—be inspired.” If that’s what you truly want, make it happen. Intention is the only requirement. The rest unfolds once you decide to leap.
But let’s be honest: most people aren’t willing to take the risks required. That’s why they stay stuck, dreaming rather than doing.
For me, two lines from the poem have anchored my life ever since I first read them.
The first is about actual troubles versus imaginary ones:
“I would perhaps have more actual troubles, but I’d have fewer imaginary ones.”
This hit me hard. To embrace this, you need courage—courage to step back and question the fabric of society’s expectations. We’re conditioned to live within a rigid framework: stable jobs, nuclear families, the “one true love” narrative, pretty houses, nice cars, and endless consumption. And behind all that? A relentless pressure to aspire for more, no matter how much we already have. The system depends on it.
But here’s the kicker: most of these so-called “troubles” are self-imposed. Imaginary. Manufactured by a culture that equates safety and status with happiness. When you see it for what it is, the whole facade crumbles. You realize the only real troubles are the ones you face while chasing something that sets your soul on fire.
The second idea that stuck with me was the focus on moments:
“Oh, I’ve had my moments, and if I had to do it over again, I’d have more of them. In fact, I’d try to have nothing else. Just moments, one after another...”
I read that line while studying abroad in Rome, during one of the most transformative periods of my life. I remember asking myself: Why can’t life be a series of moments, one after another? Why settle for a handful of memories when I could choose to fill my life with them? That realization became my guiding principle—to leap from one meaningful experience to the next. Epic adventures, big risks in love, business, and community: I’ve chased them all.
This mindset isn’t about envying others. It’s about creating what you want for yourself, one bold decision at a time.
Now, at 55, I think a lot about my own mortality. Not in a morbid way, but as a practical reality. The average life expectancy for men in the U.S. is about 76 years. Let’s face it: if we’re lucky, the ability to truly go hard at life diminishes as we enter our 70s. If I’m healthy, I’ve got about 20 solid years left—20 summers of backpacking, paddling, and surfing. Twenty winters of deep-powder skiing. Twenty unforgettable vacations with my son, friends, and family. I’m not lamenting the years ahead. I’m just desperately trying to make every single one of them count.
Twenty years is also two passports. A passport lasts 10 years, and I just renewed my fifth. I’ve kept all of them since my 20s. Those little books aren’t just travel documents; to me they’re a physical record of my moments. When my time comes, and I’m reflecting on my journey, those stamps will be my greatest treasure. Not my bank account, nor any possession. Not any business accolades or accomplishments. None of that matters in the grand scheme. All I’ll have are my moments.
Here’s the thing: if it all ended tomorrow, I’d be okay. I’ve lived fully. I’ve climbed the mountains, swam the rivers, eaten the ice cream, danced, gone barefoot, and picked the daisies. I’ve taken risks, faced real troubles, and embraced the moments. I’ve basked in the glow of amazing people along the way, collecting friends who are family across the globe and sharing my moments with them.
Think hard about that. If it all ended tomorrow, is there something you’ve put off? Are you saving up for a moment that may never come? Are you sacrificing experience in service of fear—fear of risk, fear of the unknown, fear of trying and failing, fear of instability, fear of reality? Because that is exactly what Ms. Stair prescribes as “living so many years ahead of each day.”
Today is the day. Now is your moment.