How I got (moderately) rich by investing in myself and my family

Fair warning: this post is all about decisions I made and why I made them. If you don’t want to hear about that, skip it.

I just agreed to purchase the home of my wife’s and my dreams in Portland, Maine. And pretty soon we will move there and own it, free and clear. This looks like a pretty good final chapter in my career and my life. I started to wonder, how did I get here? And are there lessons in that?

Don’t trust people who strike it rich

Consider 100 people who take a lot of risks in their careers. For 95 of them, those risks don’t pay off. For the remaining five, they do. Who do you think is blabbing about their brilliant decisions?

The five people who got lucky. They write the books and give the speeches. You never hear from the other 95.

This is, of course, survivor bias. It’s why you shouldn’t trust people who tell you to “take risks” and “follow your passion.” Of course, that works out sometimes. And it doesn’t work out a lot of the time. If your livelihood is at stake — especially if you have a family — then making high-risk career decisions may not be the best choice.

You also have to wonder about how much suffering comes along with those high-risk decisions.

I chose a different way to pursue success. At each juncture in my career, I did this:

  • Strived to do something new and interesting that would stretch my abilities and teach me new skills.
  • Attain a better situation that I was in — including an increase in compensation.
  • Do work that was fulfilling.
  • Plan carefully so that when I did take risks, I had the resources to recover if I failed.

That’s not a way to get filthy rich. But if you do it continuously and consistently, you’ll keep getting better off. And it can pay off financially in the long run.

What investing in yourself and your family looks like

Here are some decisions I made along the way, according to the principles above.

  • I leave graduate school (MIT math Ph.D. program) to take a technical writing job at Software Arts, the company that created the first spreadsheet. That generates a steady income, but it is also far more rewarding emotionally than doing graduate work in an obscure mathematical subfield.
  • I take a management/leadership role at that company, one that doesn’t come with a raise in pay. I thought it was worth it to learn about managing projects and people. (It was.)
  • I am offered a job doing options valuation at a 40% pay increase. I turn it down. It seems sterile and boring.
  • I join a startup called Javelin Software. That is my first management job. I find it challenging and rewarding. I receive stock, but it never pays off.
  • I join a startup called Mathsoft. I become a VP and run the parts of the product organization that do not involve coding or marketing. It is a rewarding way to combine my math background and new responsibilities. While Mathsoft goes public, I bail before that happens and miss out on a $750,000 payday but get enough money to buy a house. My wife and I pick a house that nobody else wants which is more affordable.
  • I join a startup called Course Technology. I get a chance to learn book creation and production, which is fascinating. The company eventually gets acquired; my stock is worth about $12K.
  • I get bored with book production. I hire my own replacement and help start the company’s push into interactive learning materials (at the time, CD-ROM). I felt like this was a rewarding way to push forward rather than doing something that had become tedious.
  • I get laid off. I join an edutainment CD-ROM company, pre-funding, for no salary. I tell my wife if it doesn’t pay off in six months, I’ll get another job. (It is enjoyable to work on, and never goes anywhere, but I learn a lot about interactive software.)
  • I take a job as a technology analyst at Forrester Research. It seems like it would be fun to learn about new technologies and write and speak about them. It is.
  • I start a family. My wife doesn’t have to work because my analyst job pays pretty well. We buy a bigger house.
  • I keep trying new things at Forrester. I develop Technographics, which becomes the company’s survey business. I became an expert on the television industry. I am endlessly curious, and learning about these new industry trends is endlessly diverting.
  • Forrester goes public. This is the first time I receive serious money for equity, and it isn’t one of the startups that were “supposed” to make me rich. Rather than invest in expensive things like fancy cars, I pay off my house. Now I don’t have to worry about making the mortgage.
  • We decide to homeschool our kids. With my wife not working and the big house, that works out pretty well. (As I write this, one child has now graduated from college and has a job; the other is still in college.)
  • I decide to write a book. I squirrel away a year’s salary so I can quit and take the risk without putting my family in jeopardy. The CEO of Forrester rejects my resignation and asks me to write a book for the company. I agree to do that, since even at a reduced salary it is less risky than going off on my own. The book, Groundswell, written with Charlene Li, becomes a bestseller. I get to give hundreds of speeches and write more books.
  • I invent a new role helping analysts develop ideas at Forrester. I manage the development of the company’s intranet. I start a daily email for Forrester clients highlighting the best research of the day. These are all challenging and interesting tasks.
  • After 20 years, I leave Forrester when an opportunity for severance arises. I get a year’s pay. My financial advisor says I can live on what I have saved, if I need to. I use the time to write a book on writing and start an editing and coaching business. That business is successful and generates a good living.
  • I buy the house in Maine. Soon after, I’ll sell the house near Boston.

All along the way, I could have made different decisions that would have paid more. But instead, I chose decisions that would allow me to enjoy my work and keep learning. I hedged every risky decision. This is not the way to maximize wealth. But is the way to generate enough wealth to retire securely, to enjoy the trip, and to not put your future or your family at risk.

If you are making career decisions, are you trying to maximize your future opportunity? Are you leaping headlong or hedging your risks?

I’d be curious to know about your choices. What did you do, and how did it work out?

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  1. I grew up in a family where work was top of the value list. I had my first summer job at 12 and never looked back. I have worked steadily since then. My parents encouraged me to take whatever work was offered–even if I didn’t like it. This was not a good idea, in my opinion. After taking a couple of jobs that were truly awful, I landed a job at Digital Equipment in 1984, and loved the work and the people I worked with. I ended up getting laid off and taking a package in 2001. Now 20 years later, I still contract for HPE, DXC, and other spin-off HP companies where I made connections with people. I absolutely love the work–training in the D&I space now. I can’t say I ever took a risk, but with some luck and my own work ethic, I remain employed and happy. My husband and I were savers so we have enough money for retirement. He was also risk adverse in terms of employment as he was at Digital/Compaq/HP without even moving his desk. He retired 9 years ago.

    We need to figure out retirement options. Portland is a great city that I would consider, too. I have no interest in moving to the South as the climate is too hot and the politics are too Southern for me.

  2. I got lucky, although I had positioned myself to be luck-friendly.

    By my late 20s, I was going nowhere. It was the late 90s. I was working in a bookstore. I had a knack for computers, but was too broke to buy a replacement for my 12-year old Amiga. Luckily, my roommate had a low-end Mac.

    I borrowed a book on programming in C, while also learning to be a Mac superuser. I found a job selling computers and network services, tripling my income. I paid off my student loans, and continued to study in my spare time. After two years, I went back to school for computer science.

    It took a few more years to find a full time developer gig—early 2000s were a slow time for Mac devs. But I persisted, and eventually got one. After a couple years, the iPhone came out. I moved to a new job, now making triple my initial starting salary as a dev.

    Then we moved to a different city. I tried to start my own indie game studio. It didn’t work out. I took a remote job I was offered, cold, by a tiny startup back in our home city. A year later, they got acquired by an e-commerce company. I got options. Four years later, options vested. I sold some (too many) at a 35x premium, to buy and renovate a condo. But I kept many. They went up 50x in value.

    Now I’m free and clear, trying to get back into writing.

    Investing in skills and experience is the best way to be in a position to get lucky. Waiting for a long-lost relative to die, or a lottery winning, is not how to get lucky. You have to increase your chances. You have to lower the denominator by becoming a person with uncommon skills, talents, and knowledge. Then luck will have a much better chance of finding you. Or you can even just walk up and introduce yourself.

    I could have worked at any major tech company, anywhere in the world, with my deep platform knowledge. Most of them would have paid off well. Was it lucky that the iPhone came out? Maybe, but OS X was a revolutionary operating system, and I could see that, because I invested the time in learning about such things, keeping an open mind, recognizing the untapped power of the Mac and Apple, and understanding what it meant when Steve Jobs went back to Apple. It was not that risky a bet. But I could also have gone into web development, such as Ruby on Rails, or something else.

    If you can’t specialize in technology, there are other areas of complexity that are important to the systems on which the world runs. There are social operating systems. There are legal operating systems. There are cultural operating systems. If you can wrap your head around systems thinking, you can be a wizard in any context.

  3. All good, Josh! Congrats. As for me, after graduating from tiny Bethany College in WV I was a trainee in the PR department of JWT in NYC. Then moved to another agency in NY and promoted to VP by 28. Switched to in-house PR at top Wall Street investment firms EF Hutton and Drexel Burnham Lambert before landing at Sony for nearly 20 years, rising to SVP of Corp. Comm. for the US electronics biz. This is where you and I met. Was pushed out during the Great Recession in 2009 and joined a startup on San Diego called Covario. It was acquired. I received some stock option payouts. Then a whole new turn at age 60 to a professor at UNC Chapel Hill, where you guest lectured one of my PR classes. Finally, I came full circle as a visiting prof at my alma mater Bethany College. Just retired and now figuring out the next chapter. Doing a lot of jogging, walking, traveling, and reading. Oh, and every other month, “babysitting” for my 98-year-old mother in law.

  4. My dugout seat to many of your decisions has been faith affirming, Josh. I don’t believe we’re here to maximize wealth. Happiness is more closely linked to the choices we create for ourselves and relationship building proves more valuable than money in the long run.

    Excited about Portland, bravo!

  5. Josh,

    First, congrats. Sit on that screen porch and have an adult beverage and enjoy your journey.

    Second, there are many lessons to learn in your story, but I identified with this one: When making important (career and life) decisions, take the long view. Even if you don’t have a long range plan in stone, or aren’t even sure where you are going, make the decision that best positions you for your future–whatever that may turn out to be..