How to Clarify Your Goals and Redefine Success with Carl Richards (Ep. 15)
What if your financial goals aren’t really financial at all?
In this deeply reflective episode of Transition Talks, host Josh Ackerman welcomes acclaimed author and visual thinker Carl Richards to unpack the real purpose of money. Known for his iconic “napkin sketches,” Carl shares stories, metaphors, and mindset shifts that challenge how we think about wealth, identity, and success.
You’ll learn why most financial plans go sideways, not because of bad math, but because we don’t spend enough time asking the right questions. Together, Josh and Carl explore three key sketches from Carl’s upcoming book and walk listeners through real-world applications of values-first planning.
What to expect:
- Why “Tell me your goals” is often the wrong starting point
- How to separate personal aspirations from financial assumptions
- Why two people never see money the same way, and how to talk through it
- The surprising difference between speculating and investing
- And more!
Resources:
- “Your Money: Reimagining Wealth in 101 Simple Sketches” by Carl Richards
- Place a bulk order of Your Money! Use code YourMoney5 at checkout to save an additional 5%
Connect with Josh Ackerman:
- Context Financial
- josh@contextfinancial.com
- LinkedIn: Josh Ackerman
- Facebook: Context Financial, LLC
- Instagram: Context Financial
- YouTube: Context Financial
Connect with Carl Richards:
- The Society of Advice
- LinkedIn: Carl Richards
- Twitter: @behaviorgap
- Instagram: @behaviorgap
- BehaviorGap.com
About Our Guest:
Carl Richards started The Sketch Guy column in The New York Times from the hills of Utah, crafting clear, relatable insights about money with just cardstock and a Sharpie. The column ran weekly for a decade. This journey began when Carl applied for what he thought was a job as a “security guard,” only to find out the ad actually said “securities.” That slight misstep sparked a lifelong dedication to reshaping how we think about money.
Since then, Carl has become a Certified Financial Planner™, built and sold a successful investment firm, and spoken at financial and investment events worldwide from Australia to South Africa, the UK, and major economic centers across Europe, Canada, and the United States. His bestsellers, The Behavior Gap and The One-Page Financial Plan, have been translated into over ten languages and continue to resonate globally.
Through his daily podcast, Behavior Gap Radio, which now has over 1,000 episodes and over one million downloads, Carl shares new perspectives on aligning our resources with what truly matters. His latest audio project, 50 Fires, backed by executive producers Chip and Joanna Gaines, explores the intersections of money and meaning with guests like Pete Holmes, David Whyte, Krista Tippett, and his favorite guest by far, his wife, Cori.
Carl founded The Society of Advice, a community of financial planners dedicated to the craft of advice. They gather for a monthly online workshop and frequent retreats in Park City, Utah.
In 2025, Carl will release a new book that, true to form, will be unlike anything seen in the personal finance section, and you better believe there will be sketches (97 of them, to be exact).
When he’s not exploring ideas about money, Carl, a Wilderness First Responder, can be found navigating Utah’s high mountain ridges on foot, skis, or bike. Married to Cori since 1995, they have four kids, whom they consider their best friends.
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