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The 10 Most Important Lessons I’ve Learned from Hosting the Retire Sooner Podcast: Part 2

A few months ago, I published part one of the top ten lessons I’d learned from hosting the Retire Sooner podcast since 2021. Today, we round out the list with analysis and life philosophies from five more top-notch experts. It’s been a pleasure and an honor to listen to and learn financial and happiness lessons in my quest to help at least one million people retire sooner.

Lesson #6

Interview: Nancy Collamer

What I Learned: Exploring second-act careers.

Since publishing You Can Retire Sooner Than You Think over a decade ago, folks have repeatedly asked me how to navigate the “retirement grey zone.” They want to know how to phase down from full-time to part-time work. Nancy Collamer’s book, Second-Act Careers: 50+ Ways to Profit from Your Passions During Semi-Retirement, is such a favorite in our office that I had to get her on the podcast. She explained practical steps for finding a new career related to, but not necessarily mirroring, the current one. She enables people in this life stage to find purpose with engagement while adding an income stream once the primary paychecks have all been cashed.

Nancy insists you can take on a different job or career if you prepare for the challenge of shifting gears. When you dedicate your life to one thing, it’s not always easy to reverse course down the road. This vital life lesson can be financially critical to your retirement planning. Folks nearing retirement might fit into one of several categories.

Robust Second Act Career Options

These include entrepreneurs, business owners, consultants, or roles in the nonprofit sector. Nancy shares stories of happy retirees who have returned to school to pursue new degrees, taken on part-time jobs, and become mentors, coaches, or even columnists. The industries involved are wide-ranging: media, technology, the arts, and health care.

From Corporate Executive To Nonprofit Leader

Connie was an executive at one of the big consulting companies. The brutal work schedule burned her out by the time she was fifty-seven. But, instead of retiring, she shifted to a different executive role, with half the work and much less stress at a nonprofit to which she felt a connection. She loved it so much that she kept working until turning sixty-five.

Natalie The Nurse Becomes A Health Coach

Following an enduring career in nursing, Natalie chose to leverage her medical knowledge and bedside manner to become a health coach. She now guides others toward healthier lifestyle choices. By offering a more preventative and holistic approach to health, she helps manage chronic conditions for her patients.

Lisa The Teacher Becomes An Educational Consultant

After decades in the classroom, a retired teacher might leverage their in-depth understanding of education to become a consultant. Assisting schools with curriculum development, teacher training, or the implementation of new strategies allows for connection and fulfillment without the nonstop intensity teachers face.

From Owen The Lawyer To Owen The Mediator

Instead of continuing a stressful and demanding legal career, Owen became a mediator, helping business partners (or ex-partners) reach agreements outside the courtroom. He can focus on conflict resolution rather than bitter legal disputes.

Finding a second act can be emotionally and financially vital to retirement planning. Nancy helped keep my expectations realistic while providing some great ideas for options.

Lesson #7

Interview: Bill Danko

What I Learned: The Millionaire Next Door is the ultimate guide to building wealth.

Just as there are primary colors in art, there are primary lessons in wealth building, with frugality as the cornerstone. Co-author of The Millionaire Next Door, Bill Danko, is uniquely positioned to offer wisdom on this topic. This book was paramount in my own journey to make a career in the financial industry, and it was a thrill to talk with him about the power of identifying the differences between prodigious accumulators of wealth (PAW), average accumulators of wealth (AAW), and under-accumulators of wealth (UAW).

PAWs vs. UAWs

To determine if you are a PAW, AAW, or UAW, multiply your age by your realized pretax annual household income, excluding any inheritances. Divide the product by ten. The result equals what your net worth should be.

Using the example of a forty-year-old who earns $200,000 annually:
40 x $200,000 / 10 = $800,000
According to the lessons learned in The Millionaire Next Door,
If your net worth is $400,000, you are a UAW.
If your net worth is $800,000, you are an AAW
If your net worth is $1.6 million+, you are a PAW.

In other words, if your net worth matches the result, you’re an Average Accumulator of Wealth (AAW). If your net worth is less than half the expected result, you’re an Under Accumulator of Wealth (UAW). If your net worth is twice the expected result or more, you’re a Prodigious Accumulator of Wealth (PAW).

Bill wants people to practice self-imposed economic scarcity and consider what’s enough for them. He believes that focusing on wealth-building activities is much more important than displaying that wealth for social status. Financial independence allows you to do what you want on your terms. If you’d rather show the neighbor your new bright shiny purchase, you might be heading in the opposite direction. Practicing the art of delayed gratification will serve you well.

Bill has focused almost exclusively on the traits that link millionaire net-worth households together, which include the prioritization of saving, a continued and relentless focus on wealth-building activities and investing in ways that compound your wealth.

Lesson #8

Interview: Don George

What I Learned: Travel leads to retirement happiness (for a variety of reasons).

If an occasional trip is good for the soul, imagine the positive impact a life full of traveling experiences could have! Don George, the legendary writer and editor, has won numerous awards for his work. He came on the show to share what creating unforgettable memories through travel is like.

Don recounted the inciting incident that sparked his passionate scribbling and the piece that changed his career for the better. He shared some of the most poignant experiences, including an astonishing Mount Kilimanjaro story, what he learned from international cultures, and how he considers traveling a religion. He listed his favorite destinations, discussed how his dad had retired early to travel, and provided advice for other travel writers. He also gave me some details from his compilation book, The Way of Wanderlust, which I highly recommend.

Travel Is A Journey Of Connection And Personal Growth

Don looks at travel as a physical journey and a personal one. He thinks we should deeply engage in a place — get to know the locals, live as the native population lives, and avoid tourist traps. Following this roadmap can lead to meaningful personal growth and understanding. I’ve realized that my time in Spain did this for me in the late 1990s. Living with a Spanish family in the Andalusian capital of Seville and later with a group of Italian and Spanish students on Calle Miño near the Seville River was the most memorable time of my life.

Writing Is A Way To Relive Your Journey

As a travel writer, George encourages us to journal our adventures. Not only does the process preserve memories, but it allows space for us to process and understand them on a more profound level. I’ve cherished my Spanish diary for nearly thirty years!

Embrace The Unexpected

Rainy days, missed trains, and closed exhibits might be the most memorable parts of your excursions! Just because a monument is under repair doesn’t mean you can’t make a monumental day of it. Allow for an open mind so the unforeseen can become fortuitous. Don George says it’s often the accidental mishaps that lead to the most indelible and resounding triumphs.

Lesson # 9

Interview: Jan Cullinane

What I Learned: The importance of community.

A sense of belonging, support, and accountability; these benefits come with joining a community. Jan Cullinane, an award-winning and best-selling author, speaker, and consultant, showed me how vital communities are.

Jan described the most productive questions people could ask themselves to discover and measure where they are in life. She also shared her Five P’s for starting a business: passion, people, platform, persistence, and patience.


A community offers belonging and connection. Both are imperative in retirement, when most happy retirees no longer have the structured social interactions a career and office naturally provide. It’s also essential to end up in a community that suits you. A bad fit can have adverse effects.

Support System

A strong community is a support system for its members, offering companionship in times of need and reducing feelings of isolation and loneliness. The right community can promote health and well-being in retirement with physical activity, social engagement, mental stimulation, and emotional support.

Jan’s expertise helps uncover how the ability to adapt and renegotiate roles can be helpful in relationships. She addresses the importance of having a purpose in life and why women need to prepare to take charge of their own financial decisions. She laid out the ideal living options in retirement, described niche vs. non-traditional retirement lifestyles, and even waded into the psychology of money.

Lesson # 10

Interview: David York

What I Learned: How to make inherited wealth powerful rather than destructive.

David York churns out nuggets of wisdom so effortlessly that it’s easy to see why the TED Talk folks invited him onto their hallowed stage to define a new paradigm for thinking about inheritance.

An attorney, Certified Public Accountant, and managing partner with the Salt Lake City law firm of York Howell & Guymon, David is an professional in estate planning, tax, business planning, and nonprofit entities. He co-authored two books, Entrusted: Building a Legacy That Lasts and Riveted: 44 Values that Change the World, the number one business ethics book on Amazon.

Sitting down with him gave me a chance to finally ask a question I’d desperately wanted answered for quite some time: Is inherited wealth powerful or destructive?

It’s a topic I struggle with out of concern for my kids. I also think about all the families I’ve advised. Some have enhanced their lives with inherited money. Others let it ruin them. I had never been able to crack the code. Luckily, David was on the case.

The answer, as you might imagine, isn’t simple. Despite witnessing many failed situations, David and his team focused on the positive. “My partner and I sat down and said, ‘What are the common characteristics of families that actually do successfully transfer wealth?’” It turned out that the families who successfully transferred wealth, first and foremost, “knew who they were, what they valued, and what they believed.” They had clarity about their “why,” which drove everything else.

He says that one of the problems with inherited wealth is that while it offers financial freedom, it can strip people of their purpose. He mentions billionaire Warren Buffet’s famous quote to “Fortune” magazine in 1986, saying he would leave his children “enough money so that they would feel they could do anything, but not so much that they could do nothing.” David says that once financially secure, too many people put down the compass that has guided them. “They just go rudderless, and that’s part of what creates the problem.”

He finds that the people who do it right don’t just prepare their wealth for their children, but they also prepare their children for wealth. It’s not just about transferring assets in the most tax-efficient way; it’s also about passing down the wisdom and attitude it takes to possess them.

“If I’ve learned one thing, it’s this; we value things based on their cost. And what’s interesting is when you look at a wealth creator, how did they earn their wealth? Hard work. Risk. Stress. Sleepless nights. Worry. All of those things. As a result, they highly value their wealth because it costs them so much.” The paradox, he went on to say, is that inherited wealth helps the offspring avoid these same traits. Parents toil and suffer to accumulate enough money to help their children avoid that struggle. What they don’t realize is that they are undercutting the very values that are needed.

Take that for what it’s worth. Life is about balance. If you prepare the right way for an inheritance, it can be a gift. If not, it can be a curse.


Hosting the Retire Sooner podcast has allowed me to act as a conduit between my audience and people at the top of their fields of expertise. We take the craftsmanship of our guests and move it down the assembly line of ideas. The hope is that the finished product, a happy retirement, will be constructed more efficiently. We’ve come a long way, but we will continue our quest to find people who can help reinforce the habits, activities, and variables that lead to a happy retirement.


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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