Simple Isn't Easy: Carl Richards on Life and Retirement

Oct 1, 2025

Carl Richards, a financial advisor-turned-artist and the mind behind insightful sketches in personal finance, discusses the power of 'elegant simplicity' in retirement planning. He shares his journey from sketches to best-selling books, emphasizing the importance of knowing your true desires, influenced by social cues. The conversation covers how to gather actionable information, balance heart and logic in decision-making, and the significance of experimentation to clarify retirement goals. Discover how to replace work identity with meaningful pursuits!

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ANECDOTE

How A Whiteboard Sparked A Career

Carl Richards began sketching on a whiteboard when clients gave him blank stares and suddenly they understood complex ideas.
That moment hooked him and led to a New York Times column and his sketches becoming conversation starters.

ADVICE

Use Short Sketches To Start Money Talks

Carl designed his new book as a coffee-table conversation starter with 101 short sketches and micro essays.
Read any page in under three minutes to spark conversations about money with others.

INSIGHT

Simplicity Comes After Complexity

Elegant simplicity requires doing the hard work on the messy middle before arriving at a clear choice.
Simplicity on the other side of complexity is valuable, unlike naïve simplistic answers.

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SHOW NOTES

In this episode, Roger Whitney sits down with Carl Richards, a financial advisor-turned-artist, to talk about keeping retirement planning simple and meaningful. They dive into the idea of “elegant simplicity,” the importance of knowing your goals, and making decisions that actually work for you. Plus, hear inspiring stories from club members to help you rock your retirement!

OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN

(00:00) The ultimate goal in building a retirement plan of record is elegant simplicity

CHAT WITH CARL RICHARDS

(02:00) Roger introduces Carl Richards.
(03:50) Carl started sketching to help explain complex financial concepts.
(07:33) Roger asks Carl about his new book coming out in October.
(11:00) Roger and Carl talk about the differences between simplistic and elegant simplicity in retirement planning.
(17:55) How do you decide when you have enough information to make a decision?
(22:19) There are many different types of decisions that need to be made- Decisions where you need a lot of research versus decisions where you already have all of the information.
(26:58) Writing makes decisions tangible versus rehashing them in your brain
(28:19) Carl talks about mimetic desire and figuring out what it is that you really want.
(39:45) Carl says he loves the idea of experiment design.
(41:40) Carl talks about living a life of meaning.
(46:50) There is a deep source of identity and purpose that comes from work. When you remove that, what do you replace it with?
(52:58) Carl talks about competing values.
(55:00) Roger talks about the Retirement Life Lab in the Rock Retirement Club

SMART SPRINT

(56:43) In the next seven days, review your retirement plan and look for ways to simplify it so it’s easier to manage.

CONCLUSION

(57:37) Roger says that what stuck out to him from the conversation is how difficult it can be to truly know what we want and how easy it is to just grab someone else’s goals, when what we really need is to slow down and take the time to define our own so we don’t end up living a life that doesn’t fit us.

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