My Give-a-Damn Is Broken: What Experience Teaches You

John Bradley "JJ" Jackson

24 Apr 2026 • 2 min read

Experience is a great teacher. It is also a relentless one.

Inspired by “My Give-a-Damn Is Broken” by Delta Blues Brother*

“My give-a-damn is broken…
And it finally set me free.”

Six months into retirement and a move to Washington state, I’ve noticed something subtle but powerful. My tolerance for nonsense dropped. Not a little. A lot. Zero tolerance.

Call it age. Call it experience. I call it efficiency. Clarity.

The blues lyric says it better than I can. It didn’t break all at once. It wore down. Piece by piece. Years of meetings that went nowhere. Endless debates with people who valued argument over substance. Watching smart people waste time on problems that didn’t matter or maybe didn't even exist. While well intended, the waste was plainly evident.

Experience is a great teacher. It is also a relentless one. Like a dog with a bone. No quit.

The upside over time is that you start to see patterns better faster. You hear the first few sentences and already know how the story ends. You recognize the difference between confidence and competence. Between motion and progress. Between noise and signal. The muted gray tones separates into black and white.

Does that make me right all the time? Not even close. I still make mistakes. But I make them faster. I correct them faster. And I move on faster. What has changed is this. I no longer feel obligated to engage. I say no more easily. I walk away more quickly. I choose more carefully. I am less polite.

That applies to life. It applies even more to investing.

As an angel investor, I am not looking for perfection. I am looking for patterns. A real problem. A credible team. Evidence that someone, somewhere, actually cares enough to pay for a solution.

I’ve seen loud founders who are dead wrong. Still talking like they’ve got it all figured out. I’ve also seen quiet founders who don’t say much but know exactly what matters. Experience teaches you which is which.

And here’s the truth that took me years to learn. Call me a slow learner. Not every opportunity deserves your time. Not every argument deserves your voice. Not every person deserves your energy. That is not cynicism. That is discipline.

My broken give-a-damn is not about caring less. It is about caring better. I still care deeply. Just more selectively. About family and friends. About meaningful work. About founders solving real problems with integrity and grit.

Everything else? It can pass by. Strange thing. When that switch flips, you realize how heavy it all was.

And how much lighter you feel without it.

P.S. Check this music video out by Morgan Luna (AKA Delta Blues Brother): https://www.youtube.com/watch?v=Fj7WrYPDLDo