The Most Dangerous Day in Retirement with Dan Haylett

Informed Decisions Independent Financial Planning & Money Podcast

In this week's episode, I chat with Dan Haylett, Director of TFP Financial Planning in the UK, author of The Retirement You Didn’t See Coming, and host of the Humans vs Retirement podcast. Dan has built his career around helping people prepare for retirement in a way that goes far beyond the numbers, focusing on the human side of life after work. Together, we explore:

• Why retirement is less a maths problem and more a human challenge.
• The dangers of the “blank canvas” problem and why day 182 of retirement can be the most difficult.
• Dan’s five pillars of a thriving retirement: purpose, identity, relationships, structure, and wellbeing.
• The concept of memory planning—turning money into meaningful experiences rather than just numbers on a page.
• Why modern retirees are “first-generation retirement rebels” and how to overcome the fear of spending after decades of saving.

I hope you find this episode, full of insights for anyone thinking about how to make the most of their second half of life—financially, emotionally, and personally. Paddy What Will I Do All Day? by Patrice Jenkins — a short, self-published book full of stories and insights from retirees, which Dan describes as a "wonderful punchy read" TFP Financial Planning Dan's LinkedIn Disclaimer

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