EP: 045 The Human Side of Retirement w/ Dan Haylett

Retirement is a huge milestone, but as many are beginning to realize, it’s about so much more than just making the numbers work. On today's episode, 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.

**If you want to check out the book, make sure to buy it direct from Dan here vs. Amazon**

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.

Key Takeaways:

Retirement is a Human Issue, Not Just a Math Problem: 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.
The Big Myths Need Busting: 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.
Expect an Emotional Rollercoaster: 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.
The Five Pillars to Thriving: Purpose, Identity, Relationships, Structure, Well-being: 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.
Retirement is a Team Sport—Communication Matters: 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.

You can watch the full video of our conversation on YouTube here:

You can also find the audio versions on places like Spotify, Apple Podcasts and wherever else you listen to your favorite podcasts.

Make sure to check out Dan's work below:

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