
Episode 283: Rethinking Retirement: The Emotional, Purpose-Driven Side of Life After Work with Dan Haylett
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What if the hardest part of retirement isn’t financial—but emotional?
Retirement isn’t the goalpost we’ve been taught to chase. It’s a major life transition, and according to retirement researcher and financial planner Dan Haylett, many people arrive unprepared—not because the math is wrong, but because they never planned for what comes next.
Melissa Joy, CFP® sits down with Dan—author of The Retirement You Didn’t See Coming and host of the Humans vs Retirement podcast—to explore the emotional landscape of retirement and why most planning misses the mark. Together, they unpack the “Retirement Reinvention Curve,” a three-phase, eight-stage model that reflects the psychological shifts retirees experience.
They go beyond the portfolio to talk about identity loss, the illusion of a permanent vacation, and how to find rhythm, purpose, and joy in life after work.
Whether you're preparing to retire or helping clients make the leap, this conversation will shift your perspective on what truly matters most.
💡 Key Themes Covered:
- Why financial planning should be 70% life and 30% numbers
- The five pillars of a thriving retirement: Purpose, Identity, Relationships, Structure & Wellbeing
- What most people miss when they focus only on "retiring from" instead of "retiring to"
- The emotional curve of retirement—from shock to elation to flourishing
- How to navigate identity loss when the job title goes away
- Tools for couples to align their personal and shared retirement visions
- Why your post-retirement rhythm matters more than your withdrawal rate
- How relationships shape retirement happiness more than wealth
🔗 Resources:
- Dan's website: www.humansvsretirement.com
- Podcast: Humans vs Retirement
- Book: The Retirement You Didn’t See Coming
- Connect with Dan: LinkedIn – Dan Haylett
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