Dads, This One's for You
Aug 20, 2025
My son, who’s twenty, is going through a storm in his life as we speak.
He’s torn between a dream he’s chased since he was four years old and what he actually wants to do.
Does that resonate with you? It sure as hell does for me.
Sitting on his bed with him last night, I parroted a question I once heard Tim Ferriss ask: “Son,” I said. “What would you do if you knew you could not fail?”
I try not to tell my son what to do. I like asking questions instead. Questions are the answer.
His eyes widened. “I’ll have to think about that one.”
As I’m writing this, it’s 7:15 AM.
He’s asleep.
I’ll have to wait for his answer later this afternoon; when most kids his age rise from quasi-hibernation. In the meantime, while I’m waiting for his answer, I’m asking myself that same question, time and time again.
The answer is always the same, every time.
What would I do if I knew I could not fail?
I’d write a novel.
As I think about it more, by not doing what I would if I knew I could not fail, am I setting the best example for my son? Am I self-sabotaging?
This one’s for all the dads out there: what would you do if you knew you could not fail? What’s more: if you know what that is, and you’re not doing it, are you setting the best example for your children? Are you self-sabotaging?
I don’t know, which is why I’m asking the question.
Because questions are the answer.
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