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Episode #4 | Carl Richards: Guarding Contentment – The Secret to Financial Life Planning?

“On the gap between our values and our actions—misalignment angularity, I would call it—there’s pain there. This is what it means to be a human. The process of real financial planning is to get those two circles closer, right?”

– Carl Richards

Whenever he flies, Carl Richards asks the pilots if they make a detailed flight plan. They say yes. He then asks how often they stick to that flight plan. They say never. Conditions always change mid-flight, and they too must adjust. Carl argues that the same sort of micro-adjustments are essential to living a life of deep peace and contentment. He also shows us how such thinking can help us avoid the handful of catastrophic mistakes that can, and often do, decimate financial futures.

About Carl Richards

Carl Richards true WELLth podcast

Through his simple—yet deeply insightful—sketches, Carl Richards (CERTIFIED FINANCIAL PLANNER™, author, speaker, artist, and creator of the Sketch Guy column featured in The New York Times since 2010) makes complex financial concepts easy to understand. His sketches have also been featured on major outlets like NPR’s “Marketplace,”, and, and serve as the foundation for his two books, The One-Page Financial Plan: A Simple Way to Be Smart About Your Money and The Behavior Gap: Simple Ways to Stop Doing Dumb Things with Money. Carl currently resides in New Zealand with his family.

Show Notes

I had the pleasure of working with Carl for a two-year period when we both served as thought leaders at The BAM Alliance. During that time, I came to know Carl as a man of deep integrity and a curious mind. When Carl spoke of “guarding contentment,” my ears perked up—at the time of this interview, it felt like my life was going through a period of contentment-deficit!

The concept Carl discussed in this episode that really brought it all home to me was his story about the time(s) in his life when he tried to push against headwinds and how those contrast with the times in his life when he felt “in the flow” thanks to tailwinds. Today, I regularly use that litmus test to ensure that the way I spend my time and my money are in the best alignment as possible with what matters most to me in life. If I’m feeling too much headwind, I know it’s time to reassess what I’m doing. To me, this is the essence of “financial life planning” and the benefit that can come from working with a truly holistic financial advisor. I hope that, combined with the takeaways listed below, listeners will walk away with a new mental model to assess the benefits of working with a fiduciary. [4:30]

Manisha’s Top Takeaways

  1. You can make the most detailed financial plan out there, but the results are only as good as the assumptions.
    No one on the planet will ever know in advance if all of their initial assumptions will end up being correct. That’s why financial advisors don’t give you a definitive prediction about your financial future. Instead, they share what we call a Monte Carlo simulation, a summary of thousands of computer iterations of potential scenarios to give you a range of possible financial outcomes. [8:00]
  2. It’s vital to review your financial plan periodically.
    As actual market, economic, saving, and spending results materialize, you should adjust your plan to reflect this past “known data.” This step will help you make any new adjustments necessary. It is the financial planning equivalent of the pilot resetting their flight plan mid-air as conditions change. [9:40]
  3. It’s possible to experience the same situation in a dramatically different way with the simple but profound mindset shift.
    Carl experienced this first hand when he let go of his typical belief that “making money is a grind.” He opened up his mind to consider viewing life through the lens of his wife’s belief: “Making money is fun and easy. It can be an adventure.” This shift was a game-changer for him in terms of thinking from a place of abundance versus scarcity. [14:50]

Other Major Topics

  • Contentment guarding: The active process of routinely assessing what, if anything, in your life is draining your contentment and setting a plan to close the gap between your current actions and your core values. [17:00]
  • Carl’s life values exercise: A fun yet profound way to discover the gap between your core values and your daily actions, combined with encouragement to be gentle with that gap [19:00]
  • Carl’s key habit: Learn Carl’s surefire habit to reboot himself back to a foundation of contentment. [22:00]

Resources Cited in the Episode

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