Welcome back to Financial Behavior Thought Leaders, the podcast that takes you behind the scenes with the brightest minds in financial services. I’m your host, Dr. Mary Bell Carlson, and in this episode, we’re diving deep into the realities of retirement with special guest Dan Haylett—retirement well-being guide and pioneer, author of The Retirement You Didn’t See Coming, and host of the Humans vs Retirement podcast.

Dan joins us to flip the script on what life after work really looks like. We explore why retirement is more of a human challenge than a math problem, and why nailing down your numbers is only the beginning. Dan shares insightful stories, the journey behind his book, and how his simple yet powerful sketches help clients and advisors alike navigate the unpredictable side of retirement. We’ll also uncover the moments that catch retirees off guard—like those quiet Tuesday mornings—and why focusing on purpose, identity, and well-being is just as essential as financial planning.

Whether you’re a financial advisor, event planner, or someone approaching retirement, this episode is packed with practical wisdom, a bit of humor, and hard truths to help you or your clients thrive beyond the spreadsheets. Get ready to be inspired, and don’t forget to share this conversation with anyone looking to make the most of life after work.

Key Takeaways:

1. Retirement is More Human Than Mathematical: Dan underscores that, while financial planning is crucial, true fulfillment in retirement comes from addressing human needs—purpose, identity, and connection. Without engaging these deeper issues, even the best financial plan will fall short.

2. Mastering Transitions Requires Preparation Beyond the Numbers: Many retirees are blindsided by the emotional and psychological adjustments that come after leaving work. Dan’s keynote and book reveal that the “retirement you didn’t see coming” is often the one in which there is no plan for life’s structure and meaning after the initial honeymoon period fades.

3. The Power of Visual Storytelling: Dan’s use of hand-drawn sketches, inspired by Carl Richards, helps demystify complex retirement transitions and puts clients at ease. Visuals become a bridge to difficult conversations and allow clients to see their situations from new, accessible perspectives.

4. Advisors Hold Unmatched Privilege and Responsibility: Financial professionals are in a unique position to shape the retirement experience. Dan believes that by asking powerful questions, allowing for silence, and embracing deeper conversations about values and aspirations, advisors can make a far greater impact than simply optimizing spreadsheets.

5. Freedom Without Structure Can Be Overwhelming: Dan points out that while the concept of freedom appeals to many, unstructured time in retirement can lead to paralysis rather than happiness. The best retirements belong to those who proactively design a life filled with purpose, connection, and meaningful activities—not just financial security.

Don’t forget to check out Dan’s book, The Retirement You Didn’t See Coming, and learn more about his keynote at FinancialBehaviorThoughtLeaders.com. And for more candid discussions on retirement, tune in to Dan’s Humans vs Retirement podcast.