Don't Be a Jerk

A Letter From My 80-Year-Old Self


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This episode started with a hard moment of self-awareness.


It was a quiet comment from my wife and a security camera clip I didn’t expect to watch. Then, I had a realization that I was rushing through the very moments I’ll one day miss the most.


So I tried an exercise that stopped me in my tracks. I wrote a letter, as if I were 80 years old, waking up in my 41-year-old body for one single day.


What came out was emotional, grounding, and deeply clarifying. In this solo episode, I slow everything down and walk through the exercise, the moments that inspired it, and the mindset shifts that followed. This isn’t a productivity episode. It’s a presence episode.


If you’ve ever felt like life is moving too fast, you’re always optimizing for “later”, or you’re succeeding on paper but missing something real: this one is for you.

In this episode, we explore:- The moment I saw myself clearly (and didn’t like what I saw)


- The letter I wrote from my 80-year-old self (and why it broke me open)


- Why the “arrival fallacy” keeps us chasing the next milestone


- A simple daily prompt that changed how I show up as a father, partner, and leader


- How imagining the ending can radically improve the way you live today


- Why helping others may be the clearest path to a meaningful life


This episode is raw, personal, and intentionally slower than usual. You don’t need to be a parent to listen. You don’t need to be 41. You just need to be human.

If it changes even one ordinary day for you, it did its job.


⏱️ TIMESTAMPS

00:00 – A hard conversation & an uncomfortable realization


02:00 – Watching myself through someone else’s eyes


04:30 – The exercise that changed everything


05:00 – Reading the letter from my 80-year-old self


13:30 – Why ordinary days are the ones we’ll miss most


19:50 – A dark career moment and the mindset shift that saved me


26:00 – “Everything works out in my favor” (and why it works)


37:50 – Imagining the ending as a daily decision-making tool


40:30 – The question I ask before every moral decision


42:00 – The one lesson I hope my kids remember


45:00 – A quiet closing invitation to try this yourself

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Don't Be a JerkBy Healey Cypher