Dan Haylett: Redefining Success in Retirement | Holistic Guide to Wealth Management

The most dangerous day of retirement is a psychological challenge more than a financial one.

By Rory Henry CFP®, BFA™

For CPA Trendlines

When most people think about retirement planning, they picture spreadsheets and savings targets. But as Dan Haylett, author of The Retirement You Didn’t See Coming and host of the Humans vs. Retirement podcast, explains, the real challenge of retirement is not mathematical—it’s psychological. 

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“People focus on the numbers because they think that will solve all their challenges,” Haylett says. “But retirement is a complex human problem. Spreadsheets will not tell us who we are without a business card or what gets us out of bed in the morning.” 

Haylett distinguishes between “complicated” and “complex” problems. For instance, he says a tax return is complicated but solvable, while retirement is complex—filled with uncertainty, emotion, and shifting identity. That’s a huge distinction, and Haylett argues that advisors who only solve the math side miss the messy human side of the client relationship. 

Haylett urges advisors to help clients plan beyond their finances – for instance, how they will structure their days in retirement, as well as their relationships and purpose. “Retirement is an emotional human transition,” Haylett says. “It requires people to think about who they are, what they are doing, and how their relationships might change.”