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The 10 Most Important Lessons I’ve Learned from Hosting the Retire Sooner Podcast: Part 1

The first episode of my Retire Sooner podcast dropped on April 1st, 2021. By then, I’d already been hosting Money Matters on WSB radio for more than a decade, but I just couldn’t pass up the opportunity for long-form interviews, thoughts, and analysis from the nation’s best and brightest. So, my team and I set up our microphones and hit record. Our mission was to help a million people retire at least one year sooner, or at least a little earlier than they ever thought possible.

Two years into this massive undertaking felt like the right time for reflection, so I compiled a list of the ten most important lessons I’ve learned thus far. We’ll start with five and then finish up in the next installment.

Lesson #1

Interview: Data Scientist, Seth Stephens-Davidowitz

What I Learned: Exactly what humans describe as ultimate happiness.

Seth has a unique way of understanding what people really want rather than what they say they want. As a data scientist and former Google employee, he doesn’t rely on answers compiled from survey questions or interviews. Instead, he uses Google Trends to dig deep into troves of anonymous search query data to see what people are asking about and searching for when they don’t think anyone is looking. This approach removes the inherent bias that can accompany the typical question-and-response method. It’s a little scary, but hard to argue with the results.

Seth found what he believes to be the hard and fast answers to ultimate happiness — what people want in this world. First, humans want to be by the water — overlooking a lake, river, or ocean. Their ideal temperature is around eighty degrees. They yearn to sit beside a romantic partner and experience intimacy — cuddling, hugging, or sex. Whoever coined the drink “Sex on the Beach” was really onto something.

Along with search data, Seth references the Mappiness Project, where people worldwide checked in multiple times a day (via smartphone alerts) to rate their happiness levels. The study instantaneously captured the participants’ actual states of mind and location through geolocation.

It determined the things that make people the happiest. What blew me away was how far “work” was down on the list — number thirty-nine out of forty! So it looks like retiring sooner is more crucial to happiness than ever!

Lesson #2

Interview: Guru and Author, Ken Honda

What I Learned: The difference between happy and unhappy money.

In the United States, it’s effortless to fall into the trap of underappreciating income and over-agonizing expenditures. Perhaps property taxes seem too high, gas prices are through the roof, and parking tickets always strike when we’re most vulnerable. Culturally, as Americans, we resent these things, and those emotions can create an unhealthy relationship between us and our finances.

Ken Honda, the author of Happy Money: The Japanese Art of Making Peace with Your Money, flipped this on its head. He taught me how to reverse my personal money dynamic. Those who know me were surprised by how quickly his words changed my perspective — literally the minute after our interview. Of course, I’m still not perfect, but I’ve used him as an inspiration to be more grateful.

Part of the trick is to understand the root of where the money is coming in. Rather than visualizing the paycheck, imagine the people who pay for the services you provide. In Ken’s case, it’s his readers. One day, when his daughter thanked him for buying her an ice cream cone, he told her his readers deserved the thanks. Without them, he wouldn’t have been able to buy it.

His teachings can also be helpful from an investment perspective. Financial decisions are always easier in retrospect. We often make mistakes in real time but can appreciate our imperfect investments for the fruit they have borne.

Ken Honda stands out as an indelible muse. As a financial advisor, I’m trained to find ways to help your assets to appreciate, and I may not always focus on ways for you to appreciate your assets. It was a foreign concept to me, and that’s why I’ve been thinking about it ever since.

Lesson #3

Interview: Writer, Editor, and Speaker, Emily Esfahani Smith

What I Learned: Happiness is overrated relative to finding belonging, meaning, and purpose.

Emily’s four pillars are mighty: belonging, purpose, storytelling (how you tell your story), and transcendence.

A sense of belonging is critical for happy retirees. It’s something that we all need to continue to work towards. Humans are social animals, and we can’t survive without a community.

Purpose means having a robust list of core pursuits that help give our lives meaning — an essential ingredient for a happy retirement. Emily’s words reminded me to focus on the purpose I set for my podcast. Purpose can help retirees find a reason to get out of bed every day.

Storytelling is vital because we all arrange our different experiences into a compelling narrative that allows us to define ourselves and the world. Without a good story, our wisdom is locked inside, unable to be shared with those who need to hear it.

Transcendence is about getting out of our own way to zoom out and view the world from a broader perspective. For example, a bird’s eye view can help us realize that rather than being alone, we are all connected.

Lesson #4

Interview: Writer of design, technology, science, and culture and author of Beginners, Tom Vanderbilt

What I Learned: The older we get, the more we stop looking for and trying new core pursuits.

Tom Vanderbilt was inspired by his young daughter’s insatiable need to know how to do everything. So, in his book Beginners, he spent a year learning purely for the sake of learning, attempting chess, singing, surfing, drawing, and juggling. But, of course, he didn’t expect that the adventure of learning those skills would be even more gratifying than any end result.

Tom does a great job explaining the critical lessons he learned on his journey, how folks can reclaim their identities by learning something new, and why failure can be a good thing. The positive aspect of beginning again with those first few awkward steps is more important than the negative.

My team and I were fascinated by his pursuit to continue learning new skills and inspired to explore our own childlike wonders in retirement.

Lesson #5

Interview: Legendary author of “Tuesdays with Morrie,” Mitch Albom

What I Learned: Giving is Living.

Prolific author Mitch Albom describes his most famous book better than I ever could: “The last class of my old professor’s life took place once a week in his house, by a window in the study where he could watch a small hibiscus plant shed its pink leaves. The class met on Tuesdays. It began after breakfast. The subject was The Meaning of Life. It was taught from experience… Although no final exam was given, you were expected to produce one long paper on what was learned. That paper is presented here. The last class of my old professor’s life had only one student. I was the student…”

His books have sold more than forty million copies worldwide; if you ask me, that number is too low. So, when the opportunity arose to interview him, I didn’t even need Ken Honda’s grace to feel maximum gratitude.

Mitch did not disappoint. Drawing from some tips he’d picked up courtesy of his former professor and mentor, Morrie Schwartz, Mitch offered wisdom about how current and future retirees can plan for the future while living for today. In addition, he stressed the importance of positive thinking and giving to others.

He admitted that he has a beautiful and privileged life, but that hasn’t stopped him from finding ways to give. In 2010 he founded the Have Faith Haiti Mission & Orphanage in Port-au-Prince. He said, “I never sleep better in my life than when I’m on a four-inch mattress in ninety-something degree heat down in an orphanage in Haiti because I wake up to the sound of children outside my door and knowing I am needed there. That sense of peace and giving allows me to sleep better than the fourteen-inch mattress and the foam pillow and the perfect temperature and all the rest of my very comfortable home. There must be something to be learned from that.”

All my research confirms that there certainly is. Volunteering is the number one core pursuit for the happiest retirees on the block (HROBs). Giving is living. It’s that simple.

As you can see, we’re lucky to get some incredible guests on the Retire Sooner podcast. I’ll be back in a future article to share more of the gold they’ve spun.


This information is provided to you as a resource for informational purposes only and is not to be viewed as investment advice or recommendations. This information is being presented without consideration of the investment objectives, risk tolerance, or financial circumstances of any specific investor and might not be suitable for all investors. This information is not intended to, and should not, form a primary basis for any investment decision that you may make. Always consult your own legal, tax, or investment advisor before making any investment/tax/estate/financial planning considerations or decisions. The views and opinions expressed are for educational purposes only as of the date of production/writing and may change without notice at any time based on numerous factors, such as market or other conditions.

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