Intentional living – winning or otherwise

Good advice is tricky. The This Time is Different series is built around asking: Are these the correct lessons?

Part of the uncertainty is the truth and fit between the big idea and the story. In Start with No, the big idea is our ego, the story is sales, and the fit is: good salespeople have the right ego. Do people have egos? Are people in sales? Does the right ego for sales still matter? Yes – so the book is good advice. 

In Wanting: The Power of Mimetic Desire in Everyday Life, the big idea is network structure, the story is about mimetics the fit is: we are mimetic due to our network structure. That checks out too (though doubt the effect size). 

Winning by Tim Grover follows this pattern. The big idea is intentionality told through the story of winning a competition. Winning like Jordan or Kobe requires intentional actions. That checks out too. In Early Retirement Extreme, the big idea is intentionality but the story is financial philosophy. The same big idea but a different story. 

Grover focuses on intentionality in two ways: wants leading to actions and outsider status.

For Grover, wanting to win has to lead to acting to win. “If you don’t get on the same level,” Michael Jordan told one teammate, “It’s going to be hell for you.” Jordan was one of the first players to switch from carb-heavy meals to eating steak before games. Before Jordan, few players trained during and before the season. For Kobe, the actions were learning Slovenian to trash talk Luca Donic. In 2008, preparing for the Olympic Games, Kobe was going to the gym when the rest of the team came back from a party at five in the morning. 

Intentional living requires wants which require actions.

Grover’s second point is how it feels to be an outsider. Howard Marks popularized the idea that outperformance means being different and being right. Easy to say, hard to do. 

Investors, like Marks, can be different and right with good stakeholders. If limited partners don’t ‘get it’ the business plan can’t work. So investors look for LPs who will ‘stick with it’. It’s easier to be an outsider when surrounded by a collection of insiders. 

Grover’s clients are in the entertainment business and the ‘get it’ is social. Why succeed unconventionally when you can fail conventionally? 

To succeed as an outsider someone must have a plan and stick with it rather than stick your finger in the wind. “No,” Grover writes, “is a complete sentence.” Build up the don’t give a fuck muscle too. Some think it’s weird? Who cares! Successful outsiders will design easier paths. Kobe Bryant had the most ingenious form and LARPed as the Black Mamba. Winning wasn’t a great book. I hoped for more insider stories. But the big idea was a good reminder. 

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