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Curiosity Chronicle · July 29 · 9 min

Stop Making a 5-Year Plan (Do This Instead)

"So, what's your 5-year plan?" That was the question posed to me by a mentor in January 2021. At the time, I was about seven years into my career, on the "track" in finance. Climbing slowly up the mountain, I had started to wonder if it was the wrong one. I just didn't seem to have the same energy for the work as most of my colleagues. All of the future mountains I envisioned were (at most) one degree of separation from the mountain I'd been climbing. As I reflect back on that moment now, in July 2026, at the endpoint of that five year plan my mentor asked about, I have an interesting realization... ••• This episode brought to you by: DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online. Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place. Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed. Lemon - The Al agent that turns your voice instructions into finished tasks.

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transcript

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show notes

"So, what's your 5-year plan?"


That was the question posed to me by a mentor in January 2021. At the time, I was about seven years into my career, on the "track" in finance.


Climbing slowly up the mountain, I had started to wonder if it was the wrong one. I just didn't seem to have the same energy for the work as most of my colleagues.


All of the future mountains I envisioned were (at most) one degree of separation from the mountain I'd been climbing.

As I reflect back on that moment now, in July 2026, at the endpoint of that five year plan my mentor asked about, I have an interesting realization...


•••

This episode brought to you by:

  • DeleteMe - DeleteMe makes it quick, easy, and safe to remove your personal data online. 
  • Origin Financial - Your personal AI Financial Advisor. Track your spending, investments, and net worth—all in one place.
  • Innerbody Labs - A Higher Standard. After reviewing thousands of health products, we built formulas we wished existed.
  • Lemon - The Al agent that turns your voice instructions into finished tasks.
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