Episode 991 is a punch-in-the-mouth reminder that sometimes the safest thing you can do… is go for it.
In this episode, I share a note Steve Jobs emailed to himself before his Stanford commencement speech — back when he and Steve Wozniak were just two guys with no wives, no kids, no house payments, and nothing to lose. They weren’t investing in better apartments or fatter bank accounts. They were investing in themselves.
And that’s the heartbeat of this episode.
If you’re young — I’m talking high school, college, early career — this is your season to explore. You can take the hit. You can start over. You can move cities. You can try something and hate it. You can fail and regroup. The walls haven’t closed in yet. So don’t build them yourself.
If you’ve got some miles on you — like me — this message is just as important. Because now you’ve got something young people don’t: wisdom. Experience. Knowledge. Judgment. And that can either become fuel… or it can become fear.
In this episode, I talk about:
Why “nothing to lose” is often when you have everything to gain
The difference between reckless and playful risk
One-way doors vs. two-way doors (most decisions aren’t permanent)
Why starting with free is powerful
How writing and starting this podcast at 43 changed my entire trajectory
And why succeeding at not trying is the quietest failure of all
This isn’t about burning your life down.
It’s about pushing the walls out before they close in.
It’s about remembering that you can always start over. I’ve been bankrupt. I’ve been homeless. I’ve been demoted. And I’m still here. Still building. Still young at heart.
Sometimes when you have nothing to lose… You have everything to gain.
If there’s something pulling at you — something you know you need to explore — this episode is your nudge.
Let’s go.
Always keep it simple.
Keep it moving.
Never settle.
Stay tough.