“When you come to a fork in the road, take it.” – Yogi Berra
I’ve written several times about the key decisions we make as adults: what we choose to do, where we choose to do it, and with whom.
But there are other decisions we make earlier in life that are just as important. In fact, they shape our intellectual and emotional development and determine to some extent the choices we are given as adults.
My three big adult decisions were to have a family with K; to live in Ndjamena, Washington, DC, and Florida; and to make a career in publishing.
But those are the broad strokes. My life – as all lives – is more complicated than that. It is crisscrossed with dozens of amazing places I’ve come to know, scores of deep and rewarding relationships, and hundreds of business and personal ventures that have enriched my time on this planet immeasurably.
I’m going to think about those early decisions that charted my life. Today, I’m going to talk about 10 decisions I made along the way that led me to the career I’ve been so fortunate to have had.
10 Decisions That Made My Career
- Forming 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. This first club idea was a puerile version of the Guardian Angels. I met with the local police chief and he gave me advice. I thought up rules and made uniforms. The Junior Police Club had only about a half-dozen members, but it was a start. It led to my becoming president of Alpha Omega Theta, a high school fraternity, and then to creating The Oxford Club, the Highlander Club, and The Wealth Club – three multimillion-dollar businesses, two of which continue today.
- Deciding to become a serious student:I was an underachiever. Mrs. Grow, my 10th grade homeroom teacher, said I was the biggest underachiever she’d ever known. I’m not sure why I preferred being the class clown to a serious student in high school, but midway through my senior year I tired of it and began to do my homework. My grades shot up almost immediately. In college, I became every teacher’s go-to student in class. I graduated magna cum laude and continued as a top student in a master’s program at University of Michigan and as a Ph.D. student at Catholic University. I became a working-class pseudo-intellectual, an identity I’m proud to own.
- Deciding to start the pool business:I had an entrepreneurial bug long before I knew what an entrepreneur was. I cleaned toilets when I was 7, cut lawns when I was 10, delivered newspapers when I was 12, had a house painting business at 16, and started an above-ground pool installation business when I was 17. The last one became a real business with actual employees, equipment, and an office in the basement of my partner’s house. This gave me a taste of being a boss, an appetite no salaried job, however glamorous, could ever match.
- Deciding to join the Peace Corps:I had a Master’s Degree from the University of Michigan and was working as a bartender near my hometown on Long Island when I got the call. I’d been accepted as a Peace Corps volunteer for a stint teaching English Literature at the University of Chad in Africa. I knew nothing about Africa, but I said yes. Two years later, I could play rugby, speak French, and knew my future would include spending a lot of time abroad.
- Deciding to get rich:About five years after I got back from the Peace Corps, I decided that I wanted to get rich. That changed my perspective on working overnight. I mutated from a disgruntled, left-wing journalist to a fledgling businessman and copywriter. Eighteen months later, I became a millionaire.
- Deciding to retire for the first time:When I was 39, I decided to retire. By that time, I had an eight-figure net worth and figured it was a good time to enjoy a life of leisure. I bought a warehouse, converted it into a library/art gallery/auto garage, and spent 18 months painting and writing poetry. I had a hell of a good time, but I was spending money faster than my investment accounts were earning it… and so I “decided” to go back to work. This taught me a great deal about the relative value of money.
- Deciding to go global: I teamed up with a publisher in Baltimore. My job was to grow his business. One of the first things we did was open an office in England. After that, we started businesses in Germany, France, Ireland, Australia, South Africa, India, Brazil, and China. Some did well. Some did poorly. But I wasan international businessman, and that felt good.
- Deciding to not care about money: By the time I was 49, my net worth had quintupled. I vowed I would never again work for money. I stepped down from running all the businesses I owned and spent the next 10 years writing and teaching. I wrote a dozen books and published an advisory blog that had 900,000 readers. But I couldn’t stop caring about business.
- Deciding to get back into business:I continued writing and teaching but began to refocus most of my working hours on business. My main business, which had grown to about $300 million by then, more than quintupled in the next 10 years. I decided to retire for the third time.
- Deciding to forget about retirement:I went to see a shrink for two years, hoping she would help me retire. She gave up on me. She said I was hopeless. I took her word for it. Since then, I’ve been happy knowing that I won’t ever stop working.