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The Life of a Plan

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

(originally published by Booz & Company)

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Sad to say, I found no real hidden treasures, just dozens of outdated cards from people who have long since left their positions.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.

Rules for Retirees
Now it’s Donald’s turn. He knows it’s put up or shut up for his plan. His “someday” is today. He’s excited and a little bit nervous. I’ve been coaching him through his transition, and I’ve told him to relax; he’s a talented guy and there’s every reason to believe he will be successful. But counseling Donald has forced me to think about the lessons I’ve learned in putting my own plan into action. Basically, I can offer him three rules to go by.

First, expect it to be harder than you expect it to be. Jim, another friend, teaches at Northwestern University’s Kellogg School of Management. But he had to market himself for a year to get an appointment. Those same deans who were so warm when he was an executive with summer internships to dole out were less encouraging when he became just another job applicant. After he got his professorship, it did not get any easier. He had to learn how to design a course curriculum, work his way up to more interesting and regular courses, and establish a reputation among students. Three years on, he’s still working at earning a student ranking in the top 10 percent of all teachers at the school, and he spends hours poring over course evaluations. His fellow faculty members are not especially helpful, either. The phrase retire to academia offends those who have invested years in getting Ph.D.s and spent decades writing papers and teaching classes. From their perspective, Jim cut to the front of the line.

Second, expect every second career to require new knowledge and skills. Jim found his 30-year career provided fodder sufficient for one lecture. Three hours of life lessons and war stories were plenty for his students. For the other 10 classes, he had to master the literature and assemble course material just like any freshly minted Ph.D. Even when the step from the current career to the next is a relatively small one, there are still things to learn. My executive friends who have joined boards stay up until midnight cramming on Sarbanes-Oxley and compensation committee bylaws. We’re knowledgeable and successful people, so of course we know something about the new careers we plan to go into, but that doesn’t mean we know enough. Knowing about good wines and how they are made is not the same as being able to make them.

Finally, expect to invest up front in building these skills and this knowledge. Any gig worth having will be hard to get. Don’t count on learning on the job. If you haven’t already learned, you might not get the chance. Donald’s colleague Mac is terrific at shaking down donors for his museum because he studied the fundraising process as a volunteer at the local PBS station for 20 years. I wrote two pretty bad books before I wrote five pretty good ones. Jim guest-lectured in night classes while still working at his day job. When he made his pitch to be an adjunct professor, he went armed with reference letters from tenured professors that praised his preparation and his rapport with students. The second careers many of us hope for are even more competitive than our first ones. For example, there are many more CEOs who make a million dollars a year than there are writers who make half that. The competition will only increase as more and more baby boomers hit that “tween” time.

A prominent CEO once told me he thought the perfect life would be divided into three equal parts: one-third making money, one-third teaching, and one-third giving the money away. It’s a lovely, compelling vision: life neatly sequenced into locked and numbered compartments like boxcars on a train. But I think it’s wrong. Speaking for myself, unless I live to be 165, the sequencing thing is never going to work. And I have children — my life isn’t a freight train clicking along a neat set of rails; it’s a freight train hit by a mudslide.

In the real world, I think you have to start on the next career before you finish the current one. No matter how connected you are or how much aptitude you have for your passion, building a career takes years, not months. To be ready at 57 means starting at 52. Or even at 47, just in case the corporate music stops early and you’re the one without the corner chair.

My agent assures me the movie people will call someday. But it’s not going to happen quite as smoothly and as quickly as I’d first thought. If you want to talk about it, drop by. I’m the guy sitting alone at the signing table at your local Borders. And don’t forget to buy a book.

Reprint No. 05303

Author profile:

Sam Hill, formerly a vice president at Booz Allen Hamilton, is cofounder of the Helios Consulting Group. He has written two novels, Buzz Riff (2004) and Buzz Monkey (2003), both published by Carroll & Graf (U.S.) and Orion (U.K.), and has authored or coauthored three business books: Sixty Trends in Sixty Minutes (Wiley, 2002), The Infinite Asset (Harvard Business School Press, 2001), and Radical Marketing (HarperBusiness, 2000). He can be reached at
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