Carl Richards: A Conversation About Money and Mid-Life

Messy Middlescence is thrilled to share their conversation with Carl Richards.

Carl who? – you might ask.

Tina asked Tara that exact question when Tara – breathless with excitement – informed her over the summer that she had secured an interview with Carl. It turns out Tina did know of him through his 50 Fires podcast (which Tara often refers to here on Messy Middlescence) but was unaware of the VERY BIG DEAL that Carl Richards is in the world of finance/financial advising.

When you listen to the interview today, you will quickly understand why. This 27 minute interview is packed with an amazing amount of story-telling, practical advice, and interesting outlooks and ideas.

Carl Richards is the beloved “Sketch Guy” from The New York Times, a bestselling author, speaker, and host of Behavior Gap Radio and 50 Fires podcasts.

He is also smack in the middle of middle age which is the primary focus of this interview and differentiates our conversation from the many others he has done recently for his new book, Your Money: Reimagining Wealth in 101 Simple Sketches.

Tara and Tina discuss with Carl many of the complex yet common issues of mid-life which showcase his financial insights along with his creative (yet often simple) solutions. Carl has a unique perspective on most things which are guaranteed to make you think.

Some of the topics covered today include:

• The most common question Carl receives from successful people as they progress through middle age
• Carl’s “Project Half Life”; what it is and its value in Carl’s life
• How those approaching retirement can help themselves feel less “stuck”
• The concept of having your future (regardless of age) be bigger than your past
• The importance of having interests/hobbies/connections beyond work before you retire
• How his advice is often simple but not easy; that sometimes the most difficult part is giving yourself permission to think differently
• The shifts that mid-life is bringing to Carl
• The beauty in breaking things down and starting small regardless of the problem
• The recommended first question to ask those close to you about money
• And what it really means to live with tension — not trying to solve the mess, but learning to sit within it

With wisdom, humor, and humility, Carl reminds us that “money is just a door to meaning,” and that midlife isn’t an ending — it’s an invitation to start again, one small step at a time.