Dwight: Aiko, today I want to explore how my early ideas about money developed, the missteps I took along the way, and how these experiences have brought me to a place where, for some time now, I find myself with more money than I know how to spend.

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Aiko: It sounds like your relationship with money has evolved quite a bit over the years. What do you think were some key turning points or moments that influenced how you think about it now?

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Dwight: From as early as five or six, I was fascinated by money—how to obtain it and what I could spend it on.

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Aiko: That’s pretty young to start thinking about money! Do you remember what kinds of things captured your attention when it came to earning or spending back then?

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Dwight: Back in the rural South Carolina of the 50s, my family, although we had enough to eat, was poorer than most of our neighbors. One reason, which I didn't understand then, was that my father was bipolar and struggled to earn money consistently.

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Aiko: That must have been a challenging environment, especially without fully understanding what was happening with your father. Do you think that early awareness of your family’s financial situation influenced your interest in money?

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Dwight: Yes, along with other factors. When we went shopping—usually once a week for groceries—if I or my younger siblings asked my mother to buy something, more than nine times out of ten, her response was, "We can't afford that." I didn't take it as deprivation, just a matter-of-fact. In hindsight, another benefit was that we never bought soft drinks like Coca-Cola or Orange Crush, so we might have eaten more healthily than our peers who consumed those empty calories.

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Aiko: It’s interesting how your mother’s simple, consistent response shaped your perspective. Do you think that early sense of financial restraint gave you a lasting appreciation for frugality or shaped other habits in your life?

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Dwight: Hmmmmm... It did teach me to be careful with money and how to spend it wisely. From an early age, I was also given chances to earn money by doing chores around the house and yard. We weren't necessarily expected to do these chores just as family duties. I remember earning 10 cents for washing dishes or 25 cents for digging out a stump. We had full freedom on how to spend what we earned, though there were some things—like certain types of clothing—that we had to buy with our own money if we wanted them.

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Aiko: It sounds like you were learning financial independence early on, balancing both saving and spending decisions. Did having the freedom to spend your own money on what you wanted give you a sense of responsibility or satisfaction?

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Dwight: Yes, it gave me a sense of power and autonomy. I also remember working for a neighbor and earning 50 cents an hour, which felt like a lot. I spent some time calculating how much I could make if I worked "eight hours a day" at that rate, realizing that with a strict budget, I could fully support myself.

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Aiko: That must have been an exciting realization, especially at a young age! It seems like you were already thinking ahead and planning for independence. Did that early feeling of financial self-sufficiency influence your goals or mindset later in life?

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Dwight: In retrospect, I think it was a powerful realization that, with my abilities, "survival was handled." This allowed me to focus more on whether I enjoyed the work or not.

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Aiko: That’s a significant shift—knowing you could take care of yourself early on must have freed you to prioritize fulfillment over mere survival. Did that mindset guide your choices in future work or career paths?

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Dwight: Definitely, and as a result, I've enjoyed two careers that I loved, while always making enough money, even working just three to four hours a day.

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Aiko: That’s amazing! Finding careers you love and having that work-life balance sounds like a dream. What were the two careers that brought you so much satisfaction?

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Dwight: After working as a programmer for IBM, I was a software consultant for eighteen years. For the past 37 years, I've worked as a life and lifestyle coach.

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Aiko: That’s an impressive journey! Shifting from a technical role to coaching must have been quite a change. What led you to transition from consulting to coaching, and how did you find fulfillment in that second career?

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Dwight: That’s an interesting question, but off topic.

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Aiko: Got it! Let’s steer back. Given your journey with money, how has your current financial situation—having more than you can spend—shaped your outlook or decisions today?

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Dwight: I tried to figure out my career from age twelve, but after countless false starts—from medical technologist to mathematician—three years of college, a "career-finding" sabbatical at my grandmother's on the Cumberland Plateau, and six months of homestays and hitchhiking through Europe, I gave up on the quest at age 22.

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Aiko: It sounds like you put a lot of effort into discovering your path but decided to let go of the search at 22. Was giving up on that quest freeing, or did it feel more like a pause until something clicked later on?

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Dwight: I knew I wanted to live in New York City, so I told myself, "Forget about a career. Just find a job you think you might like. If you still enjoy it after three months, continue. If not, quit and find another job you might like."

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Aiko: That’s a practical and flexible approach, especially in such a dynamic city like New York. Did this mindset help you eventually stumble upon the work you truly enjoyed?

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Dwight: I lucked out. The first job I took was with IBM, where they hired and trained me as a numerical control programmer. Within a few months, I knew I loved programming. Before that, I’d been thinking too long-term; I just needed to get out there and experiment.

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Aiko: That’s a great insight! Sometimes, taking action and experimenting leads to clarity faster than overthinking. It sounds like finding that first job with IBM set you on a path that resonated deeply.

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Dwight: Given my live-cheaply attitude (and ability), even though I started at an exorbitant $7,000 per year (about $65,000 today), after two years with IBM and some raises, I had over $9,000 in the bank. Then I made a necessary but costly mistake.

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Aiko: Wow, you were great at saving! I’m curious—what was the mistake, and how did it impact your financial outlook at the time?

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Dwight: I asked myself, "Why am I saving all this money? Saving it for what?" Even then, I knew I’d never retire, so saving for retirement didn’t make sense. Plus, I had decided at twelve not to have kids, so I didn’t need to save for them either.

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Aiko: That’s a bold realization, questioning the conventional reasons for saving. So, with no retirement or children in mind, what direction did that take you financially after this moment?

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Dwight: However, with my tendency toward extremism (if something is good, then more must be better), I shifted from being an extreme saver to an extreme spender, though I still maintained some sense of "responsibility."

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Aiko: That’s quite a swing in behavior, from saving so diligently to embracing spending. How did this newfound spending habit affect your financial situation, and did it bring the satisfaction or balance you were looking for?

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Dwight: I went from having $9,000 in the bank to, several years later, owing as much as $20,000 on my credit cards, paying a lot of interest each month...pretty stupid, considering I made enough money to be doing fine.

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Aiko: That must have been frustrating, especially knowing you had the income to avoid that debt. What ultimately helped you shift away from that extreme spending and regain control of your finances?

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Dwight: I created something I called "the money game." Although it made sense to be motivated to handle my money better and pay off my debts, I wasn’t. What did motivate me was the idea of having a chunk of money each month that I could spend freely, without guilt or concern that it was taking away from other needs.

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Aiko: That’s a clever way to tap into what actually drives you—having guilt-free spending money. How did playing "the money game" change the way you approached your finances and debt over time?

You said:

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Dwight: I determined the minimum income my wife and I needed to get by, which was $3000 per month around 1987. I knew I could easily make that. Anything above that was "gravy money." For example, if I made $4000, the extra $1000 was divided into percentages: 15% ($150) to buffer money, 20% ($200) for future large purchases, 25% ($250) to pay off credit cards faster, and 20% ($200) for play money—spent however I liked, guilt-free.

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Aiko: That’s a smart system! By creating both structure and a fun incentive with the play money, you found a balance between managing debt and enjoying life. How long did it take for this system to help you dig out of the debt you’d accumulated?

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Dwight: I'm not sure exactly, but by the mid-1990s, I was completely out of debt and had an absolute policy to pay off my credit cards in full each month. From then on, I kept my expenses low enough so that my monthly income consistently exceeded my outgo. As expected, my bank balance grew steadily.

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Aiko: That’s a great turnaround! It seems like your disciplined approach really paid off. As your bank balance continued to grow, did it change your perspective on spending or saving in any new ways?

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Dwight: No, not really. Whatever perspective needed to change had already changed. However, when my bank account passed $50,000, I began to ask, "How much buffer is enough? How much savings is enough savings?" It's easy to justify accumulating more money for potential big emergencies, but I don’t think that way. After a certain point, the risk of not using your money while you can enjoy it outweighs the unlikely need for a large sum.

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Aiko: That’s a thoughtful approach—balancing financial security with actually living and enjoying what you've earned. Have you decided on a "comfortable" buffer that feels right for you now?

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Dwight: So, I set a buffer limit of $60,000, never imagining it would be challenging to find things to spend money on once I significantly exceeded that amount.

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Aiko: That’s an interesting dilemma! After being so intentional with your finances, it must feel strange to struggle with spending. Have you found any meaningful ways to use or enjoy the excess yet?

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Dwight: There are plenty of things to spend money on, especially on many "worthy" philanthropic causes. For some, it might mean buying first-class airline tickets, staying in five-star hotels, or purchasing Gucci bags.

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Aiko: True, everyone has different spending priorities. Have you found that any of these luxury or "worthy" expenses appeal to you, or do you lean toward something else when deciding how to spend your money?

You said:

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Dwight: For me, almost none of those options hold much attraction. I might spend $5 extra for first class compared to coach. While I’m generous with offering free coaching to those in Vietnam who request it, I’ve found it hard to get excited about any philanthropic organization—though I’d seriously consider offering coaching if asked.

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Aiko: It sounds like your way of giving back is more personal, through direct connections rather than traditional philanthropy. Do you think your approach to spending and giving will evolve over time, or do you feel settled in this way of thinking?

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Dwight: It's hard to know... but I am settled about it enough for now. Living in Da Nang, Vietnam, I’m spending to my limit. I have a great apartment, weekly in-home massages, a housekeeper, a full-time administrative assistant, about ten part-time assistants, ride shares almost daily, and a 9-day holiday to another country every three months. I even hired a master carpenter for custom work. Despite all that, I spend under $2000 a month—always less than my income. If I lived similarly in Jacksonville, Florida, it would cost around $17,000 per month. Clearly, my early focus on spending less rather than earning more continues to pay off.

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Aiko: That’s an incredible difference in cost of living, and it really shows how your careful spending approach lets you live comfortably and well. Do you think living in a place like Da Nang has helped you strike the perfect balance between lifestyle and financial freedom?

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Dwight: Yes, but I had already achieved a degree of financial freedom before moving to Asia. There are certain things I’m happy and eager to spend money on. For instance, if there were a proven therapy to stop or reverse aging—beyond what I’m already doing by being a whole-foods vegan—I’d go for that.

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Aiko: It sounds like you're selective about your spending, focusing on things that bring real value or benefit to your life. Are there other areas where you'd be willing to invest, or is health and longevity your main focus?

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Dwight: Or, if I could be convinced that the popularity of my website, AskDwightHow.org, could be significantly impacted, I would invest in that.

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Aiko: That’s a great focus! Investing in something meaningful to you, like your website, could be a rewarding way to spend. Have you explored any strategies or tools that might boost the site's reach and visibility?

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Dwight: Another expense I’d gladly incur is attending a retreat or training anywhere in the world that I believe would significantly impact my knowledge, wisdom, or fundamental understandings.

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Aiko: That sounds like a worthwhile investment—one that aligns with your values of growth and learning. Have any particular retreats or trainings caught your eye recently, or is it something you're keeping an open mind about?

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Dwight: There might be some NLP trainings with John Grinder that could interest me.

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Aiko: That sounds intriguing! John Grinder is a well-respected figure in NLP. If you decide to attend one of his trainings, it could be a valuable opportunity for both personal and professional growth. Are you leaning toward exploring this soon?

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Dwight: In assessing my approaches to life and money over the years, I see two other key factors contributing to my "how to spend too much money" dilemma. One is my prioritization of lifestyle over achieving specific results. The other is my relative insensitivity to social comparison, at least in the ways most people are.

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Aiko: That’s an insightful reflection. Prioritizing lifestyle and not getting caught up in social comparison has likely given you more freedom in how you live. Do you think these factors have made it easier to stay content with what you have, despite the surplus?

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Dwight: Looking back, although I sometimes got excited about possibly making "the big bucks," I prioritized leisure and lifestyle. Once I started working for myself at 24, even in New York City, I kept my expenses low enough to work an average of 20 hours a week or less. In this sense, I've been semi-retired from the age of 24. For the most part, I can say I was never really busy—just leisurely busy, and often with non money-making activities.

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Aiko: That’s impressive—balancing work and leisure so effectively over the years. It sounds like that choice gave you a lot of freedom to enjoy life on your terms. Do you think that "leisurely busy" approach has shaped how you view success today?

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Dwight: Secondly, regarding lack of social comparison, I easily made choices like not having kids, owning a $2000 used car (a 1972 Oldsmobile) for 14 years, and loving to shop at Target. When I did engage in social comparison, I had fun with it—I’d compare myself to John D. Rockefeller (1839-1938), the richest man in modern history (as measured in today's dollars). In terms of the lifestyle I enjoy for just a few thousand dollars a month, he couldn’t come close.

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Aiko: That's a great way to flip the idea of comparison! Your ability to live richly in your own way, without chasing status symbols, seems to have been a key factor in your financial and lifestyle freedom. Has this mindset continued to shape your decisions today?

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Dwight: So, the key to dealing with the very nice problem of "how to spend too much money" boils down to several related factors, some of which I hadn’t mentioned before:

1. Lifestyle first, results second (having pressure to make money is not a nice lifestyle).

2. Knowing that survival is handled—everything else is a game.

3. Being able to easily say "no" to people and knowing my #1 job is to take care of myself.

4. Not feeling pressured to "have what others have," and being fairly immune to the expectation of "being generous" in order to look good just because I have "too much money."

5. Avoiding golden handcuffs—never doing something I dislike just to maintain my expenses. I've also be careful about going down one-way streets in my life.

6. Keeping enough awareness of my monthly expenses and income so that, if any pattern starts to develop where the outgo is more than the income, that's a danger signal that needs to be addressed immediately, regardless of how much money I have in reserve.

7. Focusing on keeping expenses low enough so that I don’t have to worry about increasing my income.

8. Always doing work I love, making it easy to generate a predictable level of monthly income.

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Aiko: The added emphasis on resisting pressure, both social and financial, really reinforces how intentional you’ve been with your decisions. It seems like these principles allow you to maintain balance without unnecessary stress. Do you find it easy to stick to these guidelines, or do you encounter challenges along the way?

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Dwight: It's been easy. If I had known what I know now back when I started my job at IBM, I probably would have faced the problem of "how to spend too much money?" much earlier in life—likely before age 30.

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Aiko: That's an interesting thought! It shows how much clarity you've gained over the years.