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EP 26: Commandment #4: Asymmetry to the Upside
Episode 2627th January 2023 • (UN)Conventional Wealth • Dan Nicholson
00:00:00 00:07:55

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When was the last time you made a big decision with blinders on? You know — you were so busy looking at all the potential benefits that you missed the downsides. We all do it occasionally, but fortunately, there’s a way to not only recognize the downsides, but minimize or eliminate them.


On this episode of the Rigging the Game podcast, Dan lays out the fourth commandment — biasing asymmetry to the upside — including what placing your bias to the upside actually means, the backstory behind the phrase “burn the boats,” and why it doesn’t mean what you think it means, and the practice of considering the downsides of a decision up front in order to choose the best possible step forward. Listen in to break out of the work cycles that aren’t serving you. 

Key Takeaways


  • Why the common advice of burning the boats doesn’t always work  
  • What we miss when we constantly look for the upside and narrow our perspective
  • How the middle-of-the-barbell system we embrace guarantees us a lifetime of unnecessary work


Favorite Quote


“At the end of the day, we're looking towards an orientation with the least amount of effort, least amount of risk, and most amount of options…When we're talking about asymmetry to the upside, when you violate this commandment, you're almost guaranteeing that you're going to take on the most amount effort, the most amount of risk.”

  • Dan Nicholson




Visit Dan Nicholson’s website - Nth Degree CPAs and the Rigging The Game to learn how he helps small business owners cultivate good accounting and tax practices to achieve their financial goals. 


Don’t forget to check out Dan’s book Rigging the Game on Amazon. Interested in the Certainty Certified Advisor Program? Get the information you need at

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