BigIdeas.FM: Engaging podcasts from latest books

BigIdeas.FM: Engaging podcasts from latest books

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BigIdeas.FM: Engaging podcasts from latest books
BigIdeas.FM: Engaging podcasts from latest books
Stop playing the wrong game: Build your own winnable path

Stop playing the wrong game: Build your own winnable path

Aug 07, 2025
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BigIdeas.FM: Engaging podcasts from latest books
BigIdeas.FM: Engaging podcasts from latest books
Stop playing the wrong game: Build your own winnable path
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There are games that you play and games that you really want to play.

I am not talking about sporting games literally, but the game of life.

Your goals. Your aspirations.

Many a times, we often chase goals that are ‘defined’ by the society. Instead of asking, “How do I play this game better?”, we should ask:

“Is this even the right game for me?”

a statue of a man standing on top of stacks of money

I had this moment when I actually paused and asked myself (at the peak of our media business revenue) - am I really interested in building a media business? In fact, I realized that I didn’t even want to win the game that I was playing!

Well, asking the right question helped me and am sharing a few big ideas from Graham Weaver, founder of Alpine Investors (among the top PE firms) - he shares a very interesting perspective on how to design winnable game (notes are from his Stanford lecture*).


Four Steps to Designing a Winnable Game


1. Choose a Game That Stirs Your Blood

  • Aim for goals that truly excite you and make you want to show up as your best self.

  • Aspirational goals you care about are more likely to be achieved than “safe” or moderate ones, because they inspire action and persistence.

TODO: Write down your most exciting goal daily. Assume its identity in your actions.

2. Design Your Own Game

  • The “crowded path” is rarely the most fulfilling or winnable.

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