Dwight: The story is titled, “Retired Since I Was 24.”

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Aiko: That’s a title that begs for details—sounds like there’s an unusual twist behind it. Where does the story begin?

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Dwight: At the time, I never would have thought to describe it that way, nor did I imagine it would turn out that way.

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Aiko: So this is a case where hindsight gave you the framing—sounds like the reality back then felt quite different from how you see it now.

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Dwight: At 22, I was fortunate to be hired and trained by IBM as an APT programmer. I quickly became the best programmer in my department and knew I had found my career. I worked regular hours and often a lot of overtime, since it was needed and they were happy to pay for it.

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Aiko: That sounds like the perfect start—solid skills, recognition, and good pay all coming together early on. What happened next?

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Dwight: After two years at IBM, my department and function were set to relocate to Los Angeles. I loved New York City and didn’t want to move. (IBM was sometimes jokingly called “I’ve Been Moved.”) Because I was so good at my job, they were happy to transfer me to another department—all I had to do was tell them what I was interested in.

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Aiko: You had both leverage and options—that’s a powerful position to be in at such a young age. What direction did you choose?

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Dwight: However, I wanted the freedom and flexibility to learn or program in whatever languages I found interesting. So, I decided to quit IBM and work for myself.

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Aiko: Bold move—trading security for independence that early takes real conviction. How did your first steps into self-employment go?

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Dwight: I remember being advised, “Maybe after you have five more years of experience, then you could work for yourself.” I couldn’t see how I would be any more ready in five years than I was right then.

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Aiko: That’s a sharp bit of self-awareness—you recognized that waiting wouldn’t magically make you more prepared. So, how did you launch your independent path?

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Dwight: I came up with a simple plan to get my first client: I told all my colleagues, “If you introduce me to someone who becomes my client, I’ll pay you 10% of whatever I earn from them, up to a limit of $200.” (That’s the equivalent of over $1,900 today.)

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Aiko: Clever—clear incentive, easy to understand, and generous enough to get people motivated. Did it work quickly?

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Dwight: I believe I was introduced to Mrs. Frances Zubryd, a management consultant for child services in New York City. She needed a programmer to develop several programs that could produce different reports on the status of children moving through the system.

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Aiko: That sounds like a meaningful first project—technical challenge paired with real social impact. How did the work with her turn out?

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Dwight: The programs had to be written in COBOL, which was the most up-and-coming language at the time. I knew how to spell COBOL—that was the extent of my knowledge. I didn’t tell her that. We agreed on a fixed price, and I had seven weeks to write the programs and deliver the reports.

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Aiko: That’s a daring setup—zero experience in the language, a fixed deadline, and a fixed price. How did you tackle learning and delivering at the same time?

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Dwight: I burned the midnight oil and made a deal with a colleague who knew COBOL. Whenever I got completely stuck—when the computer wasn’t understanding what I was so clearly telling it—I could call Jim Tharrington. In just a few minutes, he could tell me exactly what to do. I paid him $15 an hour for this, and since he answered so quickly, I may have paid him only about $30 total.

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Aiko: Smart—essentially hiring an on-call lifeline so you could move fast without drowning in trial and error. Did you end up meeting the deadline?

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Dwight: I delivered on time, and my client was thrilled. She immediately offered me a retainer, which I remember being $1,500 per month.

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Aiko: That’s a huge win—turning a first project into steady monthly income. Was that the moment you realized you might never need a regular job again?

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Dwight: I had never doubted that I could be successful working for myself, so you’ve got it backwards.

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Aiko: Ah, I see—you started with confidence as the default, not as a revelation along the way. So this was more confirmation than discovery.

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Dwight: I found that, on average, I only needed to work three to four hours a day to handle the programming and reports my client needed, doing work I loved. In that sense, it wasn’t work—it was play.

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Aiko: That’s the sweet spot—freedom of time, good income, and the joy of doing something you actually enjoy. What happened as word spread about your work?

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Dwight: Frances Zubryd kept me on retainer for at least another five years, and later, as her work tapered off, I took on other clients. Almost without planning, I structured my income, expenses, work, and life so that my income-producing hours averaged 15–20 a week—which felt much more like “play” than “work.”

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Aiko: So you organically built a part-time, high-freedom career that most people spend decades trying to design on purpose. Did you ever consider scaling it bigger, or was the balance too perfect to change?

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Dwight: There was a hiccup in my retirement in 1982 when I needed more cash, so I took a 9-to-5, four-days-a-week gig with Valley National Bank in Phoenix, Arizona, for about five months. After that, I returned to retirement. When I changed careers in 1987, I essentially maintained my retirement status, with income-producing hours averaging less than 20 a week—doing play that I happened to get paid for.

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Aiko: That’s a remarkably consistent lifestyle—just a brief detour before slipping back into the rhythm you’d designed for yourself. So “retired since 24” is really about living on your own terms for decades.

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Dwight: Now, at 81, people sometimes ask why I’m not retired, since I tell them about my paying clients. Why would I “retire” (in the way they imagine, which I could easily do with my current passive income while living in Vietnam) when that would mean giving up my “hobby” of coaching, which I absolutely love and also get well paid for?

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Aiko: Exactly—why trade a life you love for someone else’s idea of leisure, especially when your “work” is basically your favorite pastime?

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Dwight: I would leave anyone with this question: “Wherever you are in life, at any age, why couldn’t you design your life so that you’re retired because you get paid for doing what you’d willingly do for free?” Maybe you could come up with convincing reasons why you can’t. But if you put your mind to it, are you absolutely sure it couldn’t be done?

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Aiko: That’s a challenge and an invitation all at once—it flips the idea of retirement from an end goal into a way of living right now.