Noticing What Matters: Carl Richards on Life, Money, and Meaning

Carl Richards never set out to become the “Sketch Guy” for the New York Times. In fact, he thought he was applying to be a security guard when he stumbled into a job in securities. From that mix-up to the simple whiteboard sketches that eventually changed how we talk about money, Carl’s story is one of beautiful accidents, paying attention, and following the sparks that make life meaningful.

In this conversation, Carl shares his first memories of money, his winding (and often accidental) path, and how his restless, “always in trouble” energy as a kid evolved into a career built on curiosity and creativity. He reflects on how the mountains quite literally saved his life, why he now thinks of his work as an adventure journal, and how hosting a women’s retreat became one of the most rewarding things he’s ever done. It’s a reminder to notice what matters, lean into authenticity, and never give up on the dream of doing life your way.

Episode Highlights

• How answering the wrong ad led Carl into financial services — and the serendipity that shaped his career.
• The first whiteboard sketch that sparked a global body of work on money and behavior.
• Why Carl describes his work as an “adventure journal” rather than self-help.
• Growing up “always in trouble” — and how he’s learned to embrace the right kind of trouble.
• How the mountains have been a refuge and even a lifesaver throughout his life.
• How Carl juggles multiple projects, retreats, and writing by learning to say no — even to things he loves.
• The decision to sell his firm after realizing it had become an anchor instead of a safety net — and what it teaches about updating goals and dreams.
• The role of authenticity in our lives and this profession.
• Why intentionally creating space for women and underrepresented voices makes the industry stronger and more interesting.
• The power of noticing small sparks of joy and following them.
• Carl’s reminder not to give up on your dream, even if it doesn’t fit the mold.
• His newest book of 101 sketches, and the mission behind it: helping more people talk about money in ways that matter.