I spent all of my millions. This is what I learned

I have written about how I became a multi-millionaire at 27, and what that taught me. I was at a meditation retreat recently, when it became clear to me that I had to write this story about how I spent nearly all of that money, and what I learned in the process. I felt somewhat scared of writing this story. It felt like a kind of confession: I’m not as rich as you think I am, and I’ve made a lot of mistakes.

At age 33, I was working from home in the U.K. I lived in Brighton, a beautiful town on the South Coast, by the English Channel. I had never visited the U.K. office of my employer. I could have travelled and worked anywhere in the world. I was being paid around $200,000 per year ($220,000 to $240,000 in today’s money). I owned a five bedroom house outright, a house in a sought-after area. I was continually getting lucrative stock-option grants that supplemented my annual income by tens or hundreds of thousands per year.

I tracked my work hours carefully, and I found that I was working around twenty hours per week. In spite of this, my performance continually and consistently led to me being ranked and rated by management in the top five percent of the employees at the company. However, I still felt guilty, and thought that I was not working enough.

I was highly regarded by my peers; I was told that my engineering prowess was legendary at the company HQ in California. Earlier in my career there, I had been walking along a corridor when I heard one of the co-founders of the company say to someone from HR, “Duncan is a god!” I stopped in my tracks and quickly turned to walk away, hoping that I could avoid him the presumed embarrassment of knowing that I had heard what he said.

I also had additional cash and investments that amounted to somewhere between 1.5 and 2 million dollars. I’m telling you all this not to brag, but to let you know how blessed my life appeared to be from an outside perspective.

By this point, I had just finalized a painful divorce, a divorce that was not by my choosing. I had settled my alimony and other obligations with my ex-wife by leaving her with over one million dollars in cash and other assets. I felt at the time that this was unfair, because I had generated most of our wealth single-handedly before our son had been conceived, our son who was four at the time.

I had become disheartened with my work. After having spent years becoming a world-class computer architect, I wasn’t finding my work challenging enough. I wasn’t learning enough new things. For years, I had supplemented my learning at work by getting a master’s degree in Electrical Engineering from Stanford University in my spare time. That was now completed. I also wanted to have a greater influence in the world. As a manager, I had already realized that the hardest problems at work were not technical, but emotional and relational. People struggled with their personal lives, with motivation, and with finding meaning. I wanted to motivate people.

I felt that my life course needed to change, but I didn’t know how. I wrote an email to the CEO of the S&P500 company that I worked for, the same company that I had worked for since it was as struggling start-up, “You seem to know what you’re doing, and I’m wondering if you can help me to get clarity.” His assistant scheduled a meeting with me.

I knew that it was a privilege to get a meeting with this man, who I consider a friend, so I started preparing. I created lots of lists with titles like, “what I’m good at,” “what I’m interested in,” “what I definitely don’t want to spend my time doing,” and “what is meaningful to me.”

A day or so before meeting with the CEO, I was taking a shower when I realized that I wanted to be a motivational speaker, lead workshops, and write books. I thought that I needed to get a PhD in psychology to do this.

When I met with the CEO, I told him that I had already figured out what I wanted to do. I wanted to quit my job and get a PhD in Clinical Psychology. He told me that I should follow my heart, and that the money would take care of itself. He said that I would never have a problem getting a job in Silicon Valley, and he said that I could come back and work there full time or part time anytime I wanted. I really appreciated him saying that, and I have carried those words with me over the past decade.

I enrolled in a PhD program at a small professional psychology school in Palo Alto, California, and I started my journey of getting a PhD. At the time the school was called The Institute of Transpersonal Psychology. That was in the fall of 2007, almost ten years ago. In those ten years, I have also spent or lost most of the financial wealth I had. I lost a large chunk in the 2008 market crash, and the rest was spent in living for ten years without any income. It’s been a long decade, and I have learned a lot. I have learned a lot partly because of the mistakes I have made since I quit my job, and I have also learned a lot by reflecting on my life before I quit my job.

Before I really get started, part of me wants you to know how busy I’ve been in those ten years. I want you to know that I haven’t been lazing around. Here are some of the things I’ve been up to:

• Three years of full time psychology classes
• Two years of clinical practicum (giving people therapy for free)
• Two years of pre-doctoral internship (giving more people therapy for free)
• Preparing and filing a US patent application
• Self-representing in a UK patent dispute
• Several legal battles related to maintaining and increasing contact with my son
• Building a mobile app business (2.5 years)
• Traveling and living around the world
• Executing a randomized, double-blind, placebo-controlled research study for my PhD
• Getting lots of therapy and coaching, and attending many self-development workshops and retreats.
• Training and practice in stand-up comedy.

I remember saying to my mother on the phone, “I’m going to finish this PhD, and I’ll do it even if I have to use up all the equity in my house.” Well, here I am. I built the research devices and the web app to collect data. I have done the statistical analysis and the thematic analysis. I have a dissertation ready to be reviewed by my committee. As I am writing this my money is running out, and here are some of the things I have learned.

We’re always taking the best choices on our menus

I have found myself looking back at choices I made that I now see as being non-optimal. I have a tendency to beat myself up for making what seemed like a bad decision. It is very hard to put ourselves into the shoes of another — or even into the shoes of our past self — and understand why we made the choices we did. What we can know is that everyone is continually making the best choices they have on their inner menus.

As you read the following, it’s sometimes going to look like I’m beating myself up. I’m mostly trying to be aware of what could have been, and attempting to learn from it. I hope that I can learn, and I hope you can learn as well.

Put yourself in the path of money

The amount of money you make is not related to how hard you work, or even how much value you add. Money is flowing all around us. You make money in proportion to how much you place yourself in the flow of value transfer.

Position yourself where there is a flow of money, and facilitate it. You might also find a place where there is a potential flow of money, and create or increase the flow.

Surf big waves

Making a lot of money is like surfing. You sit in the ocean and look out to sea, looking for waves to form. You watch as waves rise up and then break. You start to anticipate how and where waves will form, and you start to paddle in that direction. As a wave approaches, you align yourself with the direction that the wave is moving, and then you begin paddling really intensely. As you feel the mighty push from behind, you jump up onto the board, and ride it for as long as possible.

You’re going to wipe-out, fall off, and face plant. This is part of the process of surfing, and particularly learning to surf. When you come off, you paddle back out to catch another wave. You don’t try to catch the wave you just fell from; that one’s done. You are learning the skill of surfing. The swell continues to come in, and the contours of sand on the bottom of the ocean will continue to throw up big waves.

“Wiping out is an underappreciated skill.” — Laird Hamilton

I made a lot of money riding on the PC wave, even while my friends were making much more on the Internet wave. Which wave I rode was an arbitrary and unconscious choice. I could just as easily have been on the Internet wave. A while back, I read a book called Bold by Peter Diamandis, which lists the current exponential technologies. These are technologies that are growing exponentially. Their growth may be almost invisible now, but they will suddenly explode, as did the PC, the Internet, and social media. I decided that I would consciously get on one of the waves he listed. As a problem solver, I chose artificial intelligence because when we solve the problem of super-intelligence—intelligence that is far greater than that of humans—all the other problems will be solved by it.

It’s never too late to learn to surf. It’s never too late to get better at surfing. It’s never too late to catch a big wave.

Biarritz, France

Consider all your options

I quit my job to get a PhD in psychology because I thought that this would enable me to lead workshops, do talks, and write books. I now understand that I could have done all of those things without a PhD. In any case, I didn’t need to quit my job to get a PhD. I had enough spare time, and freedom, to have studied and continued to work.

I also could have taken a more gentle transition. Instead of making a 100% switch from engineering to psychology, I could have got a master’s degree in counseling psychology in the evenings. Then I could have learned more about the field, and about how I fitted into it. I could have taken small, experimental steps.

I also now see how much freedom I had. I could have travelled around the world and worked remotely from exotic locations.

Ask yourself what you would like

Often the thing that you need in each moment is very simple. Perhaps you need to hear that your partner loves you. Perhaps you need to spend an hour with an old friend. Perhaps you need a walk around the block. I have had a tendency to think that when something was wrong, something really massive was wrong. I have a tendency to catastrophize. Perhaps you don’t really need to quit your job and head for a totally new career.

I have many more resources than I did ten years ago, including a much greater capacity for discomfort and uncertainty. I recommend developing equanimity through daily vipassana meditation, and getting the facilitation of a skilled coach to get clarity about what you actually need right now.

Obtain and preserve assets

People from old money learn to “never spend the principal.” This is an approach to retaining wealth, even if it means living with temporary lack. I spent ten years without any real income, and I spent the principal.

Some people spend their entire lives paying off mortgages in order to own just one home. There was a time when I owned three houses on two different continents, at least two of them mortgage-free. Now I don’t own any real estate.

I look back and realize that if I had kept my capital and invested it in index funds, and continued to work, I would now have so much wealth that I would never have to work again. I could live by taking such a small piece of the gains in the assets that the principal would continue to grow at a faster pace than inflation. I also recently realized that if I had left all of my wealth in the original company that it came from, I would now have around $35 million.

Instead, I have to work again. I have to generate income using my time and energy. It has been hard for me to accept this, but I have to remember that I made the best choices I could at the time.

Buy things you love and will use

For most of my adult life, I have been able to buy whatever I wanted, whenever I wanted. I have bought a lot of stuff. I have tended to buy many things that I never use.

Recently, we have been purging our things by following the Konmari method, as described in the book called The Life Changing Magic of Tidying Up. I enjoy selling things on eBay, or via Craigslist. I enjoy providing really high quality customer service with fast shipping. We have converted much of our stored junk into thousands of dollars in cash. I also love to see things going to people who will use them, rather than putting more stuff into the landfill. This process has made me much more aware of my purchasing habits, and much less likely to make impulse purchases.

Over the past few years, because of a general sense of not wanting to waste resources, I have become much more discerning about buying things. When I think I need something, I spend a lot of time reading reviews on Amazon, and looking for the best quality item. I also see if I can get by without it. I have various wish-lists where I record things. Those items rarely turn into purchases.

The things I do buy now tend to get well used, and treasured. As I write this, I’m wearing a pair of Bose noise cancelling headphones, which I have used the crap out of. At home, I have a sit/stand desk with an oak top that I took from a dining table. I made that desk, and I’ve used it most days for the past 13 years. Objects that we buy are tools that we use to live our lives.

Buy things you can trash

If you cannot trash it, then you shouldn’t have it. Things you buy are just tools. I once bought a car that cost me $80,000. The base price was $50,000, and I added $30,000 of options. I ended up selling it two years later for $40,000. During those two years, I worried all the time about it getting dented or scratched. One day, I might have a car that costs me over $100,000, but I won’t do that until my net worth is at least 1,000 times that: $100 million.

A car is a tool

Cars depreciate. They are not investments. It doesn’t matter if you finance or lease. It’s going to work out roughly the same either way. A reasonably functional car costs about the same every year, when averaged out over a few years. Some people regularly buy new cars because then they don’t have to pay for expensive repairs, but a new car depreciates rapidly. Sometimes when I take my old car in for a service, it needs some expensive work. I remember that the cost of those repairs and services over the year average out to the cost of owning a car.

Get unstuck

I used to get stuck and not know what to do. I didn’t even realize that I was stuck. I’ve now had enough therapy and coaching, and breakthroughs from meditation, that I know that being stuck is good. Embrace being stuck. Enjoy being confused. Find a really good coach and let them support you in getting clarity. All the time you resist being stuck, or pretend to yourself that you’re not stuck, or think that you can “do it myself,” you will stay stuck.

Be okay with not knowing

There’s a lot of value in being confused and in not knowing the answers. When I went to meet with the CEO of my company, I automatically tried to figure out the answers in advance. I now realize that I missed a massive opportunity. I could have gone into that meeting and told him, “I’m really confused. I’ve just been through a massively painful divorce, and I feel like my life has lost its meaning. All I know is that I want to do something with my life that’s more meaningful, and I want to influence more people.” That conversation could have led anywhere, and I could have got the real benefit of working with my friend, and letting him help me. That conversation could have blossomed into a powerful collaboration. Instead, I made sure I had all the answers before I spoke with him.

You don’t need qualifications

I now have two master’s degrees, and I’m about to get a PhD. Many times during my PhD process, I wanted to start a business, and I held myself back until I finished my PhD. At one point, I wanted to get an MBA, and I talked with a friend about it. The answer I got was that I didn’t need an MBA to start a business. I still proceeded with my PhD. I did take a break from my PhD, while still paying tuition, to work on an app business, but that didn’t work out.

Very early on in my PhD process, I was tired of researching and writing long and complex papers that I would not be paid for, and which often would barely be read. Yet I persisted with my PhD. This was partly because I tend to persist with things I start. Once I commit to something, I tend to find it very hard to change direction.

I suspect that part of me places formal qualifications in the way of my success. I feel that I have to get some external validation that I am qualified or capable to do something. In fact, I can coach people effectively without a PhD in psychology. I can do all the things I originally set out to do without qualifications. I can deliver talks, write books, and lead workshops right now, and I could before I even started on my PhD program.

Lifelong learning is now free

Maybe I had to get three graduate degrees to realize this. Most days I study now, and I do it outside of the framework of any externally-defined study plan. I’m getting (another) world-class education, on my terms, for free.

One example is my process of becoming a world-class expert in AI. This is one of my goals, and the way I’m currently approaching it is to take all the Stanford graduate-level classes in AI. Having gotten a master’s degree in Electrical Engineering (and CS) from Stanford, I know exactly what it’s like to go through those classes, when enrolled.

Even now I’m not enrolled at Stanford, I can watch the videos of the class I’m taking right now on YouTube. I can read the syllabus and download the slides to follow along. I can read all the documents, including the assignments. One of the most effective ways that I learn is by doing. Working through these assignments on my own is just as effective as doing them while enrolled in a degree program.

Beyond the massive amounts of free classes from top universities, many sites like Udemy and Coursera offer free and almost free classes in every subject. With an investment of only your time, attention, and curiosity, you can become an expert in anything you choose.

Get good at pivoting

Within a year or two of starting my PhD in Clinical Psychology I knew that I didn’t want to become a licensed Clinical Psychologist. I had many business ideas, and I also found myself becoming interested in organizational psychology, law, and business. I thought about getting a JD or an MBA, or starting a business, but I kept persisting with my PhD. One of my weaknesses is sticking with things that aren’t right for me. Being aware of this tendency enables me to watch out for it, and to consciously and bravely pivot when necessary.

Bite off small projects

My PhD was a massive project that took ten years. I made it way more complex and challenging than it needed to be. Instead of doing the bare minimum to get a PhD, I create a gold-standard clinical trial, along with two adjunct engineering projects. My PhD project was at a scale that would cost hundreds of thousands or millions of dollars when properly funded.

I am now determined to commit to much smaller projects, and to break larger projects down into easily completable pieces. It feels great to complete something. Once a piece is complete, and I have run the experiment associated with it, I can re-evaluate if I want to proceed with the larger project.

This is very much in the vein of the lean startup approach. I believe that it makes sense to run your whole life on the lean startup model. Always be figuring out simple experiments that you can run and get data from. Always be ready to pivot.

Avoid litigation

Even if you win a lawsuit, the cost in time and stress is usually not worth it. I have spent years going through court to try to get “justice,” or trying to get what’s best for everyone. Now that I’ve done this a few times, I understand the true cost of it. I understand that winning often looks like walking away. When you’re in a lawsuit, it’s with you all day, every day. It wears you down. It takes a lot more to get me involved in a lawsuit than it used to.

Even then when technically and legally you should win, there can be forces acting behind the scenes that lead to you losing. In my patent litigation, since the judge’s decision did not match the evidence or arguments, I suspect that some lord at the head of the patent office spoke with some lord at the head of my undergraduate university, and strings were pulled to protect the university.

Also, a court of law is not a place to resolve family issues. In law, there is a winner and a loser. In a family, that paradigm does not apply. What most people want for their family is health, wealth, harmony, and happiness. If you can’t get this outside of a court, you will certainly not get it inside a court.

Mindfulness is primary

A couple of summers back, my wife and I were staying in Biarritz in the South of France. While there, I was working on my app business. I had estimated that the business would produce around $1.4 million per year for me, once we got our subscription model working. Having burned through a lot of my wealth, and having worked for free for around 2.5 years, I was looking forward to turning my cashflow around.

During this time, I realized that we were never going to make it, and that I needed to focus my energy on getting my PhD complete. I needed to stop investing in this business that was not going anywhere. I quit the business. Even though I was in a beautiful place, with great weather, and I had a surfboard, I went into a deep depression.

My wife, Cindy, signed me up for a 10-day Vipassana retreat for when we got back to the U.S. This was to be my second 10-day retreat. During that retreat, I came out of my depression, and I realized that I needed to keep practicing every day. I became free of depression and anxiety, and I have meditated between 30 and 120 minutes per day for years now. I have been on a third 10-day retreat since then, and will go on a fourth later this year.

Vipassana meditation, which is an industrial-strength form of mindfulness meditation, is foundational for me. It’s one of the most important things I do every day. It changes my relationship with reality. It enables me to see the world, and my place in it, clearly. I recommend signing up for a free 10-day retreat near you.

Yosemite National Park

Money isn’t everything

Sometimes I look at my contemporaries who stayed on the same path, and I feel envy. Some are CEOs, venture capital partners, and distinguished engineers. Most of them are wealthy, with multiple homes. If I had stayed working, I would be wealthy and distinguished. Instead, financially, I am almost back at square-one.

Then I remember how I felt when I quit my job, and I realize that it would not have been a happy path. I can’t know for certain how my contemporaries feel, but I understand how warped I would have grown. Instead, I spent these ten years investing in myself, deepening my relationship with myself, and learning to live a balanced life.

My wife believes that I have intentionally used up the money from the first phase of my life, and flushed out that energy, in order to make space for a fresh start. This resonates with me. I have immense goals for my life, and I feel that I have created a solid foundation for them inside myself, in my intimate relationship with my wife, and with my solid tribe.

Going forward, I will thrive in life at a level that would not have been possible if I had not gone through this process of purging and recalibration.

Summary

I hope that all of this experience will fuel and support the next phase of my life. I believe that my experience with this relatively small amount of money has positioned me to handle the much larger amounts of money coming my way. I hope that you too have been able to learn something from, and benefit from, my experience.

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Updates

• This story has been republished at NY Observer.