What Could Have Been
A reflection on self-belief, opportunity, and the quiet risk of never trying.
“Twenty years from now you will be more disappointed by the things you didn’t do than by the ones you did do.”
– H. Jackson Brown Jr.
Dear Reader,
In the past couple of weeks, I had three separate conversations about work and they’ve stayed with me.
One person is in the middle of a career change. They’d stepped out on their own to try something new, gave it a real go, and it didn’t unfold the way they’d hoped. Now they’re finding their way back to the work they loved before, not defeated, just wiser.
Another had been out of work for about six months after having to close a business they’d built. This week, they finally landed an offer. The road was hard, but they came through it.
The third hasn’t taken the leap yet. She’s in a steady corporate role, quietly building something on the side, inching toward the day she can work for herself. It’s not easy, and it’s not without friction. But she can’t shake the feeling that there’s something more out there for her.
Three very different situations. But underneath them, the same thread.
Each of these people reached for something bigger. And even when it didn’t work out the way they planned, not one of them regretted trying. They pivoted. They survived it. They learned things about themselves they couldn’t have learned any other way. And every one of them is better positioned now because of it, even the ones whose original plan fell apart.
That’s the part we forget when we’re standing at the edge of a decision, afraid to take the leap.
We assume the risk is in trying and failing. But ask the two who tried, the ones whose plans didn’t pan out. They’re glad they did it.
The real risk is the quiet one: reaching the end of a chapter, or a life, still wondering what could have been if you’d only given yourself permission to try.
You don’t need to have it all figured out. You just need enough belief in yourself to begin. Because even if it doesn’t work, you’ll be okay. You’ll still have a path forward. And you’ll almost certainly be better for having tried.
My question for you this week:
Where in your life could you believe in yourself a little more and pursue a greater opportunity?
Sit with that.
– Ken