They say the three most important decisions in life are what you do, where you do it, and with whom.

That sounds right. But most of us don’t make these decisions formally. It’s not as if, when you turn 18 or 21, you get a communiqué from on high asking you to make your choices.

When I look back, I can see that each of these decisions was actually the result of a series of small decisions that seemed to lead me in some direction.

I never, for example, decided to live in Florida. I ended up here 40 years ago as a result of a misunderstanding about the tax deductibility of vacations and the advice of a stoner.

I certainly didn’t simply “choose” my life partner. I had a crush. We dated. We separated. I wrote to her. She wrote to me. Etc. Etc. There must have been a thousand small decisions involved in this big one.

As for what I do – my career – I didn’t exactly choose that either.

This is the path that (I think) got me to where I am today:

10 Decisions That Changed My Life 

  1. Deciding to start the Junior Police Club– I got the club idea from the Little Rascals’ “He-Man Woman Haters Club.” I formed it when I was maybe 12. The concept was a preteen version of the Guardian Angels. I met with the local police chief to ask his advice. (“Behave yourselves.”) I created a set of rules. We had makeshift uniforms.

Membership peaked at six, but the club thing stuck with me. It led to – in my 30s, 40s, and 50s – the creation of the Oxford Club, the Highlander Club, and The Wealth Club, all of them very successful businesses.

  1. Deciding to become a serious student – I was an underachiever. Mrs. Grow said I was the biggest underachiever she’d ever known. I’m not sure why I liked playing the clown in high school. It had something to do with a predilection for not conforming. But midway through my senior year, I decided to change and began to do my homework. My grades shot up almost immediately. In college, I forced myself to sit in the front row. I read the assignments, did the homework, and asked and answered questions. It didn’t take me long to be one of the “go-to” students in class. I graduated college with a 3.83 (out of 4.0) cumulative average, magna cum laude. And I went on to graduate school at the University of Michigan and Catholic University, where I won all sorts of academic honors.

I could have spent my life as the goof-off in the back of the classroom. I moved to the front and learned to enjoy it. 

  1. Deciding to start an actual business– I had been working part-time and on weekends since I was 12, and had every sort of job you could imagine – from waiting tables to painting houses to plating silver to selling pots and pans to writing term papers for money. Then, when I was about 20, two friends and I started Reliable Pools, a “real business” with real customers, real employees, real business cards, and real profits.

For the first time in my life, I was making more money than I could spend. In a single year, I paid off my college loans and had enough left over to fix up my parents’ dilapidated old house. It felt good. 

  1. Deciding to live in Africa – To get away from the dull destiny of my hometown, I applied and was accepted into the Peace Corps as a volunteer. I spent two years in Africa, teaching English Literature and Philosophy at the University of Chad.

I came away from that experience with a new perspective.  I became a citizen of the world. And I learned that I could be happy living a simple life in a simple house. 

  1. Deciding to get rich – About five years after I got back from the Peace Corps, I decided that I wanted to get rich. There were lots of other things I wanted to do with my life, but I decided to make getting rich my top goal and work on the others later. That decision almost instantly changed the way I worked and, more importantly, thought about work. I realized that if I wanted to get rich as an employee, I had to make my boss very rich. I did that in spades.

Within 18 months, I went from broke to millionaire.

  1. Deciding to retire (for the first time) – When I was 39, I decided to retire. I was still young and had an 8-figure net worth. I thought it would be a good time to try out my dream. I bought a warehouse, converted it into a library/art gallery/auto garage, and spent 18 months painting and writing poetry. I had a personal secretary to help me with… I don’t even know. And, yes, I was spending a lot of money. In fact, I was spending so much money that I had to either cut back or go back to work.

I tried cutting back. That lasted 24 hours. Then I went back to work.

  1. Deciding to stop caring about money – When I was 49, I realized that I had all the money I’d ever need. I decided to remove “getting richer” from my to-do list. I stepped down from actively running a large publishing company and went to work for it as a consultant. I also kept writing.

In the next 10 years, I wrote a dozen business books and published an advisory blog that had 900,000 readers. 

  1. Deciding to take my own medicine – One of the subjects I wrote about frequently on my blog was personal productivity. And when I read Stephen Covey’s book The 7 Habits of Highly Effective People, I incorporated his four quadrants of time management into my own system. Covey argued that focusing on your important-but-not-urgent goals – those that you never seem to get to because you are so busy – will change your life. He was right.

In the next 10 years, I accomplished all sorts of things that I’m quite sure never would have happened. Things such as writing fiction and poetry, producing movies, developing a family foundation, and so on.

  1. Deciding to keep working – I hired a therapist. Her job was to help me retire. I had tried to retire three times. Now that I was approaching 69, I intended to make one final and serious effort. We worked hard. We had fun. After 18 months, she told me that I was hopeless. “You should accept yourself,” she said. “Accept the fact that you like your work.”

I did, knowing that meant I was never going to retire. And since then, I have never wanted to. 

  1. Deciding to get rid of my wealth – I read too many books. I heard too many stories. Dying rich is a huge mistake. It almost always causes problems. Not money problems. Those you can take care of with proper planning. Family problems. Leaving money to others is like leaving emotional land mines. (Read Beyond the Graveby Jeffrey L. Condon.) Leaving money to charities is just as bad or worse. Acquiring wealth takes discipline and hard work. Getting rid of it does too. (That’s why Warren Buffett gave half of his wealth to Bill Gates – to let Bill figure out how to do it.)

For all of these reasons, I have decided to get rid of at least 80% of my wealth in the next few years. Instead of leaving it in my will, I’m getting rid of it now while I can see and be responsible for its effects. (Don’t ask. You can’t have any.)