On Thanksgiving: How I got lucky

I like to believe I am really good at what I do. Perhaps, but I am also very lucky. Thanksgiving seems like the right moment to look back at all the ways fate dealt me a favorable hand.

I was lucky to have been born to loving and intelligent parents. My father, raised in a working-class family, turned a competitive swimming scholarship into a degree, eventually a Ph.D. and professorship, and a solid and successful marriage. My siblings and I were raised in an affluent, suburban Philadelphia suburb and supported in all of our academic endeavors. I learned that accomplishment and success would be their own rewards, and they were. I never thought about whether that would have been true if I’d been born to different parents in a different part of the world, a different part of the country, or even a different part of Philadelphia.

My high-school experience was filled with support and learning from the best public-school science, math, and writing teachers imaginable. They nurtured and encouraged my math and writing talents. That was a big help in getting to the next stage.

Due to my father’s job as a Penn State professor, my tuition was nearly free. That set me on a track to graduate school at MIT with a National Science Foundation fellowship. While I worked hard for that, I was extremely lucky to have been blessed with the talent to take advantage of it.

Just at the moment I began to lose faith in graduate school, my fiancé’s stepfather suggested my name for a writing job in one of the first rapidly growing PC software companies in Boston. I was lucky to have that connection, and luckier still that the hiring manager took a chance on me — a writer who had never used a word processor. That break turned my life in a different direction.

I was lucky to be qualified for a succession of software-industry jobs of increasing responsibility, up to the rank of vice-president. When I eventually got laid off, I rapidly landed a job as an analyst at Forrester. I was fortunate that they identified me as someone who would make a good analyst, even though I’d never done industry analysis of any kind. I was very lucky to have the best possible teachers there to learn from — including Bill Bluestein, Mary Modahl, and Emily Nagle Green, who stuck with me after a rocky start. I was fortunate to have a coverage area, television and media, that gave me wide visibility, and to be associated with their launch of consumer research that tapped into my mathematical background.

I was really lucky that Forrester had its IPO within two years after I joined, generating a seven-figure payoff for me from a company I hadn’t launched.

Halfway through that experience, I attempted to quit and write books. I was extremely fortunate that the CEO of Forrester, George Colony, was instead willing to retain me to write books for Forrester. And I owe a debt to the coauthor of my first book, Charlene Li, whose incredible intellect fueled that book project’s success. I’m also grateful that George and Forrester continued to support me through four other book projects, establishing me as an author and business book expert.

I was also fortunate that Forrester and I were able to negotiate an exit for me after 20 years with a severance package that became the runway for building my own writing and book business. I also would never have been able to launch my writing and editing business without the visibility that had come from 20 years as an analyst.

I was incredibly lucky with my timing in the rising real estate market. My first two houses in Boston suburbs turned into well over $1 million in gains.

And I’m also grateful that a woman of incredible character, intelligence, and love — my wife, Kimberley — stood by me throughout. She was always there, not just as a partner but as a parent and homeschooling teacher to two fantastic children. Those kids are now formidable adults, and she deserves most of the credit.

I didn’t do this alone

The place where I am now — happy, healthy, loved, and doing work I enjoy every day — could never have been possible without these lucky breaks and the wonderful people who were part of them.

Sure, stuff went wrong. Nobody is lucky all the time. After my first marriage ended, I was left with no assets and had to build up again from zero. I sold my stock in one of the software startups and missed out on a $750,000 payday. After I got married again, my wife and I suffered devastating pregnancy losses before we were able to have healthy children. I was depressed for a while until I was accurately diagnosed with an easily remedied hormone deficiency. I got cancer, I got treated, and with lots of luck involved, I got cured.

The next time you see someone bragging about a success story, it’s worth asking what role luck played in their success.

Because, while I worked pretty hard and seized the opportunities that I found, I was very lucky that those opportunities were there when I needed them. I’m very thankful for everyone who was part of all of that luck that helped generate the wonderful life I have now.