Samuel “Skip” Halpern, Author of Wellsprings of Work, on Finding Meaning in Work, the Drives Beneath the Surface, and Protecting “I” from AI (North Fulton Business Radio, Episode 986)
On this episode of North Fulton Business Radio, host John Ray welcomes Samuel “Skip” Halpern, author of Wellsprings of Work, for a conversation about finding meaning in work at any stage of life. Skip describes himself as a recovering lawyer. He began his career at the U.S. Department of Labor enforcing ERISA, the federal law governing how pension and employee benefit assets are invested, then moved to the investment advisory side of the same business and now serves as an expert witness in litigation over those investments. The second edition of his book, updated to address artificial intelligence and carrying a new subtitle, Surprising Sources of Meaning in Your Career and Retirement, went live on Amazon the day before this recording.
Skip explains the dozen psychological and spiritual drives he calls wellsprings through stories from his career. A saved voicemail from Warren Buffett, who wanted to buy a block of Kaiser Aluminum stock managed by Skip’s firm for retired steelworkers, turned out to be about the desire for respect and recognition, the same thing a waitress in Studs Terkel’s Working wanted from a rude customer. Advising the Chinese government on its upside-down pension demographics taught him the pull of connecting to something larger than yourself. And an exhausting due diligence effort on a fund that called Bernie Madoff its “highest conviction position” revealed how much motivation comes from competition and play.
The conversation closes with the new chapter Skip subtitled “Protecting I from AI.” He argues that misalignment, the lack of accountability in a chatbot’s apology, and the erosion of trust all threaten to cut people off from these wellsprings, and that the greater danger is humans becoming more like machines rather than the reverse.
John Ray is the host of North Fulton Business Radio. The show is produced by John Ray and North Fulton Business Radio, LLC, an affiliate of Business RadioX®, and is recorded inside Renasant Bank in Alpharetta.
Key Takeaways from This Episode
- Finding meaning in work begins with examining the underlying motivations that people often overlook, whether in a career, in retirement, or in volunteer work.
- A saved voicemail from Warren Buffett and a waitress’s complaint in Studs Terkel’s Working point to the same wellspring: the desire for respect and recognition.
- Tying work to something larger than yourself, as Skip did advising China on its pension crisis, can be a powerful motivator, and it can leave you both proud and humbled at once.
- Competition and play are legitimate sources of meaning, as Skip learned during a due diligence fight over a fund that called Bernie Madoff its “highest conviction position.”
- Skip’s new AI chapter warns that misalignment, hollow accountability, and eroding trust can cap these wellsprings and that the real risk is people becoming more like machines.
Topics Discussed in this Episode
00:20 John Ray introduces the show and guest Samuel “Skip” Halpern
01:56 Skip’s background as a recovering lawyer, from ERISA litigation to investment advisory to expert witness
03:28 The second edition of Wellsprings of Work, updated for AI, released the day before
03:45 Enforcing ERISA at the Department of Labor and always being aligned with the workers
06:44 What to say to the cynical listener who finds no meaning in their current role
08:08 The Kaiser Aluminum bankruptcy, a block of stock managed for retired steelworkers, and a voicemail from Warren Buffett
10:26 The waitress in Studs Terkel’s Working and the shared drive for respect
11:12 Meaning as something you bring to even the most mundane job
12:09 Viktor Frankl, Man’s Search for Meaning, and meaning as something you create
13:04 Why some people find meaning in their work and their peers do not
15:06 Advising the Chinese government on its upside-down pension demographics
17:01 Tying your work to something larger than yourself
18:21 Two brushes with Bernie Madoff and the “highest conviction position”
20:06 Due diligence as a colossal intellectual arm wrestling match and competition as a wellspring
21:16 The new subtitle and why so much meaning in work is a surprise
22:39 “Protecting I from AI”: misalignment, accountability, and trust
25:24 The risk of humans becoming too much like machines
25:49 Who the book is for: new graduates, retirees, and everyone in mid-career
27:28 How to find the book and wellspringsofwork.com
Samuel “Skip” Halpern, Author and Sole Member, Prudent Expert, LLC
Samuel “Skip” Halpern has 50 years of experience over a career extending across institutional investing, law, and business.
After graduating from college at Brown University in 1972, he earned his law degree from the George Washington National Law Center in Washington, D.C. He next clerked for a federal District Court Judge in Washington and the U.S. Court of Appeals for the D.C. Circuit. He then began as a staff attorney at the U.S. Department of Labor, litigating cases across the nation under the then-newly enacted federal law regulating employee benefit plans in the private sector, ERISA (Employee Retirement Income Security Act). Those cases revolved around the responsibilities of pension, 401k, and health fund fiduciaries to prudently invest fund assets solely in the interest of plan participants.
Halpern broadened his focus in 1986, when he and a business partner founded a niche investment firm to advise employee benefit plan fiduciaries across both the private and public sectors and to act as an “independent fiduciary” when the regular fiduciaries suffered conflicts of interest. They formed the firm as a subsidiary of Bear, Stearns & Co., which at the time was one of the 10 largest broker-dealers and investment banks on Wall St. Over subsequent decades, he became the firm’s president and also served a diverse set of clients, ranging from the Major League Baseball Players Pension and 401k Plans to the World Bank, Asian Development Bank, the public retirement systems of 25 states, and benefit plans of major corporations, including banks, airlines, and industrial companies across the U.S.
He and his partner bought the firm from Bear Stearns in 1996 and renamed it “Independent Fiduciary Services.” In 2011, after they sold IFS to a public company, he remained with the firm during a 3-year transition period and semi-retired in 2015.
Then began a third chapter in Halpern’s career: acting (part-time) as an expert witness in ERISA investment litigation. That has revolved around comparing the due diligence that ERISA fiduciaries have followed (or failed to follow) in making investment decisions with generally recognized practices. He also remains as an adviser to the National Hockey Players Association regarding the investment program of its defined benefit pension fund.
Wellsprings of Work
Upon his semi-retirement, Samuel Halpern reflected on his long and varied career, wondering why he found it so gratifying. The eventual result was the first edition (2022) of the book, Wellsprings of Work: Surprising Sources of Meaning and Motivation in Work. The book identifies a dozen psychological and spiritual drives, what Halpern calls “wellsprings,” that make work meaningful. Kirkus Reviews called it “…engaging and enlightening…an informed, perceptive reflection on fulfilling work…[by] a gifted storyteller.” “Wellsprings” has been used at Brown University, NYU (college and business school), and George Washington Law School and forms the core of seminars Halpern has taught at the Chautauqua Institution.
More recently, he has updated the book, published in September 2026, with the new subtitle, “Surprising Sources of Meaning in Your Career and Retirement.” The new edition adds an extended chapter that considers how artificial intelligence threatens to obscure the wellsprings of work, plus a toolkit for putting the book’s ideas into practice, and broadly defines “work” to include not only a career but also whatever other activities people pursue in their larger and later lives, including retirement.
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About North Fulton Business Radio and host John Ray
Approaching 1,000 episodes and having featured over 1,400 guests, North Fulton Business Radio is the longest-running podcast in the North Fulton area, covering business in our community like no one else. We are the undisputed “Voice of Business” in North Fulton!
The show invites a diverse range of business, non-profit, and community leaders to share their significant contributions to their respective markets, communities, and professions. There is no discrimination based on company size, and there is never any “pay to play.” North Fulton Business Radio supports and celebrates businesses by sharing positive stories that traditional media ignore. Some media lean left. Some media lean right. We lean business.
John Ray is the host of North Fulton Business Radio. John and the team at North Fulton Business Radio, LLC, an affiliate of Business RadioX®, produce the show, which is recorded inside Renasant Bank in Alpharetta.
The studio is located at 275 South Main Street, Alpharetta, GA 30009.
You can find the entire archive of shows by following this link. The show is accessible on all major podcast apps, such as Apple Podcasts, Spotify, Google, Amazon, iHeart Radio, and many others.
John Ray also operates his own business advisory practice. John’s services include advising solopreneurs and small professional services firms on their value, their positioning and business development, and their pricing. His clients are professionals who are selling their expertise, such as consultants, coaches, attorneys, CPAs, accountants, bookkeepers, marketing professionals, and other professional services practitioners.
John is the author of the five-star-rated book The Generosity Mindset: A Journey to Business Success by Raising Your Confidence, Value, and Prices, praised by readers for its practical insights on raising confidence, value, and prices.
