The Long View Dan Haylett: ‘The Retirement You Didn’t See Coming’
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Nov 18, 2025 Dan Haylett, a financial planner and author, dives into the unspoken emotional aspects of retirement in his insightful discussion. He reveals how many retirees face identity crises and feelings of emptiness after ceasing work. Haylett emphasizes the importance of designing an engaging retirement, advising against solely leisure-based lifestyles. He advocates for gradual transitions into retirement, cross-generational mentorship, and the need for couples to communicate openly about their plans. With humor and perspective, he encourages living fully in the present, rather than waiting for retirement to enjoy life.
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Spreadsheet Success, Emotional Failure
- Dan recalls a client who had a perfect cash-flow plan but felt lost six months into retirement.
- That experience pushed him to focus on the human side of retirement planning.
The Summit Has No View
- The thrill of chasing retirement often beats actually reaching it, leaving retirees disoriented.
- Focusing only on money creates a summit with ‘no view’ and a hard, confusing descent afterward.
Knowledge Workers Face Bigger Identity Loss
- Most modern knowledge workers face identity and purpose losses in retirement.
- Retirement today is emotionally different because peak wisdom often coincides with the decision to step back.
