Some Day Isn’t Coming – Stop Postponing the Life You Want
I'll be honest with you. I was not expecting much from the drive.
Four hours. Just me and my 13-year-old. I had mentally prepared for the particular silence that parents of teenagers know only too well—the one where someone is physically present but mentally somewhere else entirely, earbuds in, thumbs flying across their phone, entirely checked out before we'd even hit the highway.
About twenty minutes in, something unexpected happened. My kid put their phone down, turned to me, and said "I want to have a serious conversation."
I almost missed my exit.
"Oh?" I said, my eyebrows raised a full three inches higher than where they would normally sit.
"Yeah. I want to ask you some questions."
"Sounds good," I said, not knowing what to expect. "Fire away."
Without any hesitation whatsoever, "What is your biggest regret in life?"
The Flood
I want to tell you I handled that with grace and wisdom. That I had some beautifully prepared answer ready to go, something thoughtful and measured that a parent would be proud of.
That is not what happened.
What happened was that the question hit me like a wave I didn't see coming. I needed a minute. I needed a lot of minutes! “Hmmm… great question. Just give me a minute to think about that one.”
And then something I wasn't prepared for happened. Things just started flooding in. Fast. Too fast. Not one regret… but many! Things I had wanted to do at various points in my life and never did. Paths I had stood at the edge of and walked away from. Chances I had let quietly expire without ever really deciding to let them go.
I felt something rise up in my chest that I was not about to let become a full on moment in front of my kid. So I steadied myself, picked one answer I could actually speak out loud, and gave it as honestly as I could.
Because here's the thing about a 13-year-old asking you that question. You can't mail it in. You can't deflect or get philosophical or change the subject. They put their phone down—a miracle in and of itself. They chose this conversation over four hours of everything else available to them. The least I could do is show up for it.
So I did.
The Advice I Needed to Hear Myself
After I answered, I said something I hadn't planned on saying. Something that came out less like parental wisdom and more like a realization I was having in real time.
"What your question made me realize," I told them, "is that the last thing you ever want is to look back on a long list of things you didn't do and wish you had. If there's something you really want—something you know in your bones means something to you—don't let that be the thing you look back on. Don't let it be the one that got away while you were waiting for the right moment or the right circumstances or worse—for some day.”
Everyone is going to have some regrets. Nobody lives a perfect life. But there's a difference between regretting something you did and regretting something you never even tried. The first one you can learn from. The second one has a way of slowly hollowing you out if you let that list continue to grow.
One Spin
In my last post I wrote about Jim, my neighbor, and his habit of always saying he's "surviving" every time I ask how he's doing. I wrote about gratitude and what it means to actually show up for the life we’ve been given. This is the next part of that conversation. The showing up.
Because gratitude alone isn't enough. Knowing you're lucky to be here isn't enough. At some point you have to ask yourself the next question. What am I going to do about it?
In that last post I said We get this one life. One spin. And the clock—as uncomfortable as it is to say this—is always running. Not to create panic. Not to pile on pressure you don't need. But because the awareness of that fact, held honestly, has a way of clarifying things remarkably quickly.
What lights you up? What is the thing? Your career? A creative pursuit? Your relationship? An adventure? The secret dream you've been carrying around for years that you know in your gut means something to you? Not what looks good by anyone else’s standards. Not what you think you should want. And especially not something that someone else thinks you should want. The real thing. Your thing.
Find it. Or if you've already found it, ask yourself, “What am I waiting for?”
Is it permission? To begin? To try? Permission to take yourself seriously and believe that what matters to you actually matters?
So many of us spend years waiting. Waiting until we have more confidence. More time. More certainty. More money. More experience. Perhaps waiting for someone’s approval. Waiting for everything to line up perfectly before we allow ourselves to start.
And yet life rarely works that way.
Most meaningful journeys begin before we feel ready. Most meaningful choices arrive wrapped in uncertainty. Most meaningful dreams require us to take a step before we can see the whole path.
What My Kid Taught Me
That road trip changed something between us. There were more questions after that one. Good ones. And by the time we arrived I felt like we had crossed into new territory together. But it was that first question that stayed with me. Still does.
A 13-year-old, on the edge of the age where parents supposedly stop mattering, chose to put their phone down and ask their parent about regret. About life. About what it all means. If that doesn't make you want to have a better answer ready—for them and for yourself—I don't know what will.
You don't have to wait for someone to ask you the question. Ask it now. While you can still do something about the answer.
What's your biggest regret? And more importantly—does it have to stay that way?
Start Where You Are
The heaviest regrets aren't usually the things we did. They're the things we talked ourselves out of. The dreams we deferred for so long, they stopped feeling like dreams and started feeling like someone else's life.
You still have time. Maybe not unlimited time. None of us do. But enough. Enough to take one step toward the thing that matters. Enough to stop waiting and start moving.
One life. One spin.
Don't let it pass you by while you're waiting for it to begin.
If this resonated with you, the Workforce Nation: Meditation for Work-Life Harmony YouTube channel here and podcast (below) explore ideas like this every week through guided meditation.
And if you haven't read the post that started this conversation, scroll back to Glad I’m Here for This – Life is About More Than Just Surviving. It's where Jim comes in.
