The Human Side of Retirement and How to Truly Thrive in Your Next Chapter with Dan Haylett

Hey everyone, welcome back to Modern Financial Wellness! I’m Jim Grace, your host, and I’m excited for this week’s episode, where we’re diving deep into the human side of retirement. Retirement is a huge milestone, but as many are beginning to realize, it’s about so much more than just making the numbers work. Today, we’ll unpack the emotional, psychological, and deeply personal challenges—and opportunities—that this major transition brings.

My guest this episode is Dan Haylett, retirement coach, financial planner, keynote speaker, creator of the “Humans vs Retirement” platform, and now an author! Dan’s work stands out for exploring not just the math behind retirement, but the untold human journey at its core. His new book, The Retirement You Didn’t See Coming: A Guide to the Human Side of Retirement Nobody Warns You About, inspired this conversation—and I can’t recommend it enough.

In our discussion, Dan shares what inspired him to write his book, why the traditional “retirement is the goal” narrative misses the point, and how true fulfillment comes from addressing five essential pillars beyond the financial. We debunk common retirement myths, highlight the complexity of the emotional transition, and talk practical strategies so you (or your loved ones) can truly thrive in this next chapter—not just survive.

5 Key Takeaways

1. Retirement is a Human Issue, Not Just a Math Problem
2. Numbers and financial security are important, but they don’t guarantee happiness, safety, or meaning in retirement. Most real challenges—and opportunities—are personal, emotional, and deeply human.
3. The Big Myths Need Busting
4. Most of us carry ingrained narratives that “retirement is the goal” or that “the numbers will make us feel safe.” In reality, many arrive with enough money but feel lost, anxious, or directionless.
5. Expect an Emotional Rollercoaster
6. Retirement is not a straight line. There’s a reinvention curve, including excitement, shock, doubt, and ultimately, flourishing—if you’re open to doing the human work. Everyone will experience ups and downs, and that’s normal.
7. The Five Pillars to Thriving: Purpose, Identity, Relationships, Structure, Well-being
8. Don’t wait until you retire to think about these. Start now! Reflect, do the exercises, talk with loved ones, and intentionally reinvent these pillars to create a meaningful and joyful life.
9. Retirement is a Team Sport—Communication Matters
10. Especially for couples, talk early and openly about your individual and shared visions for this chapter. Expectations, purpose, timelines, and how you’ll spend your days may differ—address these before you leap.

If you want to move beyond the spreadsheets and bulletproof your sense of meaning in retirement, I highly recommend Dan Haylett’s new book, The Retirement You Didn’t See Coming. It’s practical, readable, and packed with exercises to help you design the life you want.

Thanks so much for tuning in! If you enjoyed the episode, please subscribe and check out Dan’s book, podcast, and newsletter—the links are in the show description.

Until next time—here’s to your financial and human wellness!