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(originally published by Booz & Company)


The Life of a Plan

In fulfilling that long-deferred dream, it’s good to start your second career before you exit your first.

Illustration by Lars Leetaru
The other day I came across a drawer full of old business cards. I started to toss them into the recycling bin, but then stopped myself. What if I found a 1983 Bill Gates or a Jeff Bezos rookie card somewhere in the stack? So I spent a recent Saturday afternoon sprawled in front of the TV, flipping cards into a wastebasket.

Sad to say, I found no real hidden treasures, just dozens of outdated cards from people who have long since left their positions. I can no longer put faces to most of those cards, but I still keep up with a few. Donald, for example, unexpectedly retired last year at age 53, four years before his youngest son was to graduate from high school. Donald has had a good run, one that gives him some financial latitude, and he’s spent the last 10 months compiling a list of options for what might come next, something to keep him busy and plugged into the network now that his 24/7 career is over.

Donald’s looking for a plan: a way to finally do the kind of thing he’s always hoped he would do once he had the time. He wants to be like our friend John, who turns prize-winning walnut bowls in his workshop on Hilton Head, S.C., or Gordy, who works with disadvantaged youth in rural Minnesota. Of course, Donald would prefer to combine personal interest with something that also pays well — like his former colleague Mac, now CEO of a major museum. Joining a venture capital firm could work; ditto with sitting on a corporate board or owning a winery. He’s also thought about doing some writing.

The Slippery Ladder
Writing was my plan. When people ask me why I write, I laugh and say, “It plays to my skills — I can type and I like to drink.” That’s defensive humor. The truth is, I have always wanted to write and be read, from the days when I self-published my work in crayon on construction paper. My day job is terrific and I’m in no hurry to leave it behind, but my plan is to write great, enduring books that people will pull off a bookshelf at a lake cottage 50 years from now and get so absorbed in that they won’t go to bed until seven the next morning. For 10 years I’ve worked toward both aspirations — building a profitable and growing boutique consultancy while writing and publishing both nonfiction and fiction.

Last year I was invited to speak at a writers’ conference in McCall, Idaho, where would-be writers asked me what it feels like to be a published author. I told them the truth: “Way cool.” I glossed over how much time and work it has taken. Consider the math. I have written about two dozen articles and published five books. It takes me at least 1,000 hours to write a book. That’s two hours a night and five hours every Saturday and Sunday for an entire year. Over the last 10 years, I could have read 500 books, seen 500 movies, and played 500 rounds of golf; instead I’ve spent so much time at my ThinkPad that I’ve worn through the left “Shift” key. And despite a manila folder full of glowing reviews, Wednesday nights are still spent signing for nonexistent crowds at suburban bookstores, where the manager buys a novel because she feels sorry for me.

I had always assumed that once I actually started on my plan, it would come easy. I thought I would just step from the top rung of my old career to the top of my next one, that my success would be as portable as an IRA. It turns out there are all sorts of slippery rungs on the ladder, including some I never imagined. My first attempt at a novel, Stonefish, was a thick tome about a vicious serial killer pitted against a ruggedly handsome ex–Navy SEAL. As soon as the last page rolled out of the printer, I confidently stuffed it in an envelope and rushed to the FedEx box. Three impatient months later, I called my agent. Me: “Did you get the book?” Him: “Yes.” Me: “Did you like it?” Him: “Why don’t you try something else?” It had occurred to me that I might get rejected by a publisher or two. Even Stephen King got rejected. But I never dreamed I might get rejected by my own agent. I didn’t appreciate it at the time, but as a new and unproven writer I was pretty darn lucky even to have an agent to reject me.

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