When You Keep Second-Guessing Yourself
Letters to My Son… If I Had One By Fred Ferguson (GeezerWise)
Dear Son,
Some days I catch myself wondering if I’m doing what I’m supposed to be doing.
Not in the sense of right vs. wrong—I'm long past debating whether to rob a bank or run for mayor. I’m talking about those quieter questions.
The ones that creep in while I’m alone, halfway through a project, or just sipping coffee in the early morning silence:
“Is this the best use of my time?”
“Should I be doing something else?”
“Is this really the path I’m meant to be on?”
At 73, you’d think I’d have it all figured out. Truth is, the older I get, the more I realize that “figured out” might be a myth. What we do have, though, is the ability to pay attention—to check in with ourselves.
And that’s what second-guessing really is.
It’s not weakness.
It’s a form of awareness.
It means I still care.
It means I’m still awake to the possibility that something more fitting, more honest, more aligned might exist—if I stay open to it.
That doesn’t mean I chase shiny objects or quit things too soon. It just means I’ve learned to live with the question.
Rick Rubin said:
“Clarity doesn’t come before the act. It comes through the act.”
And sometimes, clarity doesn’t come at all—but peace does.
So if I had a son, I’d tell him:
Let the questions come. Let them ride beside you.
But don’t let them freeze you in place.
You don’t need perfect certainty to take the next step.
Just enough courage to be present while you walk it.
If I had a son, I’d want him to hear this…
Your second-guessing doesn’t mean you’re broken.
It means you’re still engaged.Still alive.
Still growing.
And there’s nothing wrong with that.
—Fred
This letter was written by Fred Ferguson (GeezerWise). If it spoke to you, I’d love to hear back—just hit reply.
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—Fred [GeezerWise]