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The Life of a Plan

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.

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