Make Money by Thinking of Your Older Self

Travis Makes Money

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2d ago 20:24

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In this solo-style episode, Travis sits down with his producer Eric for an introspective conversation using the “rocking chair test,” a thought experiment where you imagine advice from your much older self at the end of your life. Instead of featuring an external guest, this episode turns the spotlight on Travis’s own mindset around regret, failure, and what he wishes he’d stop (and keep) doing in business and life.

On this episode we talk about:

How the “rocking chair test” helps you see your current life from the perspective of your 88–108-year-old self
Why most people regret what they didn’t do more than what they did “wrong”
Travis’s tendency to downplay wins, fixate on failures, and how that has held him back
How his upbringing and internalized beliefs still shape his self-talk and response to criticism
The story of building a 7-figure business, losing it, and struggling to own his successes afterward
Why podcasting is the thing he’s most proud he stuck with, despite years of low direct financial return
The tension between chasing novelty and doubling down on what you’re genuinely great at
Using your future self as a filter to judge fears about embarrassment, judgment, and starting over
How meditating on death and limited time can create urgency to take bigger swings now

Top 3 Takeaways

Your future self will almost always regret the risks you never took more than the attempts that didn’t work out.
Fixating on failures while dismissing your wins can quietly cap your potential, even when you’ve built real results.
Doubling down on your core strengths for income, while using side projects to satisfy curiosity and novelty, is a powerful way to build both wealth and fulfillment.

Notable Quotes

"I tend to significantly downplay the successes I’ve had and highlight the failures I’ve had, and that’s held me back in a lot of ways."
"People on their deathbed usually regret the things they didn’t do far more than the things they did that didn’t work out."
"Life is short, and in 200 years none of this will matter—so why not just go for it and take another big swing?"

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