
The Meaningful Money Personal Finance Podcast The Retirement You Didn't See Coming, with Dan Haylett
Nov 19, 2025
In this engaging conversation, Dan Haylett, a financial planner and author, explores the often-overlooked emotional aspects of retirement. He emphasizes that retirement is less about numbers and more about redefining one’s identity and purpose. Dan highlights common misconceptions, such as the dangers of the transition period and the need for a structured approach to spending. He shares insights on the 'retirement reinvention curve,' encouraging listeners to develop meaningful projects that pull them toward a fulfilling retirement.
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Retirement Is A New Chapter
- Retirement is not the end but the start of a new chapter requiring redesign of identity, time and money.
- The real challenge is psychological: ultimate freedom brings frightening choice as much as opportunity.
Psychology Outweighs Portfolio Risk
- The biggest risks in retirement are psychological, not financial.
- Purpose, identity, relationships, structure and wellbeing determine whether retirement thrives.
Perfect Plan, Lingering Anxiety
- Dan described a client with a perfect financial plan while his wife felt anxious despite the numbers.
- The wife said, 'I know the numbers are all saying we're fine. So why do I feel like I'm waiting for something to go wrong?'

