Jon Callahan (The Great Unlearn)

Jon Callahan

Cal spent a long time chasing money, social status, and all kinds of external validation.
And he didn’t just chase it. He was good at getting it.
As an interest rate trader in Chicago, he had checked a lot of the boxes that people think will make them happy. (Including playing golf with Michael Jordan – crazy, right?)
Cal was in the audience at the Route 91 Festival shooting in Las Vegas, and – since then – his priorities have changed.
Through his podcast, The Great Unlearn, Cal hopes to share his message with other hard-charging, successful people. The happiness and validation you’re looking for isn’t on the other side of whatever mountain you’re climbing.
Check out the full episode with Cal to learn:
  • How to reframe a huge failure into a learning experience – without just engaging in stilted, corporate doublespeak
  • What Cal learned as a trader during the 2008 financial crisis that is applicable today to the situation with COVID-19
  • How to balance the necessities of playing certain “status-seeking” games when growing an audience – without falling back into traps of relying on external validation for happiness

Check out the episode at the links below. If you enjoyed the episode, the best way to support the show is to share with your friends, so send them a link.

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Check out more from Cal and The Great Unlearn here:

Show Notes:

  • [01:36] Cal transitioned from interest rate trading into fitness and was an owner of the Phoenix Rise in the National Pro Grid League – but only recently has he been able to view the failure of the NPGL through a positive light. Learn how.
  • [07:03] So, what even was the NPGL anyway?
  • [12:33] Why was Cal so hard on himself for losing money in the NPGL if he knew going into it that it was a very risky investment?
  • [20:35] Reframing a loss – and not just engaging in sanitized corporate doublespeak
  • [24:34] Cal’s personal experience as a trader in the 2008 financial crisis
  • [34:33] Did the 2008 financial crisis offer any opportunities for individuals or systems to shift out of of any negative patterns? Were we able to learn anything from the crisis?
  • [39:23] How being present at the Route 91 festival shooting in Las Vegas made Cal realize that he had been optimizing his life for the wrong things.
  • [52:14] Why is external validation so appealing? And, why doesn’t leave us actually fulfilled?
  • [58:14] How to “play the game” of building an audience – which requires chasing certain kinds of external validation – with the inner work of not needing external markers of success in order to be fulfilled.
  • [01:12:42] The writing process for Cal’s forthcoming book – and how he hopes to share his message with people who are not just chasing external rewards, but are good at it as well.

Links and Resources Mentioned

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