I’ll never forget him.
A guy I used to work with when I was still driving.
Sharp. Dependable. The kind of guy everyone liked.
But underneath all that?
You could see it—he was empty.
Same truck. Same hours. Same paycheck.
And the same look in his eyes…
Like life had slowly drained the color out of him.
One afternoon, we were waiting for dispatch, and I asked him,
“If you weren’t afraid… what would you do?”
He didn’t laugh.
He didn’t deflect.
He just paused and said,
“I’d move to the coast. Buy a little boat. Take people out fishing every day.”
I said, “So why don’t you?”
What he said next has stuck with me ever since:
“Because I’ve got bills… I’ve got pride…
And I’d rather be miserable than look stupid trying.”
Read that again.
He would rather stay miserable than risk starting over.
Now I’m not judging him—believe me, I’ve been him.
But here’s the truth most people won’t say out loud:
Most people don’t stay stuck because they’re lazy.
They stay stuck because they’re too proud to be seen starting small.
But you know what’s even harder than starting over?
Living with regret.
That man never moved.
Never bought the boat.
Never changed a thing.
And last I heard, he’s still clocking in, still complaining, still miserable.
And I made a vow to myself that day:
I will not end my life wondering “what if.”
I will not let pride steal the best parts of me.
And I will not play small just to make other people comfortable.
Sometimes the smartest, most practical thing you can do…
Is humble yourself, cut your expenses, move in with a roommate if you have to…
And give yourself a shot at real joy.
If you’re in that place right now—stuck, tired, scared—it’s okay.
But it’s not okay to stay there.
You’ve got one life.
You owe it to yourself to try.
So here’s my question to you:
What would you do if you weren’t afraid of starting over?
Let that answer guide you today.
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Steve Lofton 
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