Episode 10

Season 2, Episode 10 - Commandment #4: Asymmetry to the Upside

Published on: 27th January, 2023

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 CertaintyU.com.

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About the Podcast

Rigging The Game
The Rigging The Game Podcast is the top resource for entrepreneurs who want unconventional strategies and tips to win at business and life on their terms.

Entrepreneurs who are breaking through barriers while setting new standards in their industry recognize that the cliché, cookie cutter, and conventional recommendations about finance and business don’t apply to them.

This podcast will release you from the “WHAT YOU SHOULD BE DOING” chains so you can massively win at business and life by playing your game.

Painful shyness intersecting with an insatiable desire to compete (and WIN) birthed a relentless curiosity to understand how to massively win at business and confront fears without conforming to a set blueprint.

This show is for the purpose-driven entrepreneur who recognizes that the cliché, cookie cutter, and conventional recommendations about finance and business don’t work because they’re playing a different game.

As a painfully shy kid, I often found myself on the sidelines quietly observing the game of sports, life and business until the flames of competitiveness grew to a bonfire and took over. From the ashes, birthed a relentless curiosity and drive to understand how to massively win at business and confront my fears without conforming to a set blueprint.

I share the unconventional strategies and tips I learned to make sure you win (get what you want) under your rules. Hear all the “a-ha” moments as a business owner, dad, exercise enthusiast and serial idea generator while interviewing other thought leaders who have developed their own strategies to rig the game to win.