"'Starting at the end' means investing time up front to develop an aspirational picture of your future as a guide for the decisions you make throughout your career and your life," Howard said. "And sometimes the easiest way to define your legacy is simply to think about what you want people to say about you at your funeral." He stopped and looked at me, making sure I got it.
"I have to admit," I said after a moment of reflection, "of all the things I thought we'd talk about tonight, eulogies were not on the list. But that's what I love about you, Howard--you keep a guy on his toes."
"I could live with that on my tombstone," he joked, then grabbed his briefcase from beside the couch and turned his attention to preparing for the next day's meeting.
Remember the last time you faced an inflection point? A chance you had to confirm a path you were on, or to head off on a new one? Did you stick to your original course by default, in preference for the tried and true? Or did you pursue the option that everyone thought you "had to do"--the "once-in-a-lifetime opportunity" that you felt you couldn't pass up, even if your gut was telling you to let it go?
And how did you make your decision? If you're like most of us, you may have struggled with the pros and cons of specific options. You may have thought endlessly about the possibilities in front of you. Perhaps you focused so closely on every small element of each option that you found yourself in decision paralysis, unable to figure out what you "should" do.
Or, as Howard would suggest, did you take some time to stop, to bring all of your life's potential end points--all your myriad goals and hopes--together into a single picture? Did you then make a decision within the context of that whole-life picture?
It's easy to set a single goal and pursue it fervently. What I learned from Howard was the importance (and, yes, the challenge) of envisioning and pursuing not just that narrowly focused goal, but a broader personal legacy--a vision that holistically comprises the life you want to live.
Why is doing that so important? Because identifying your legacy is the essential precursor to creating the road map of how you want to live your life. It is the foundation for the decisions you make in your career.
How much easier is it to make all the step-by-step decisions you face--accept this job or that, live in the city or the suburbs, go to graduate school or take piano lessons--if you have a clear long-term destination in mind? The answer is obvious: enormously easier. But easier decisions are not the biggest--or even the most important--benefit. Legacy-driven decisions are also much more effective, much more likely to lead to a sense of satisfaction. In this respect, people can take a useful lesson from successful businesses.
Businesses succeed when they base tactical decisions on an overall corporate strategy, not on one small element of their operations. Those without a comprehensive strategy fail. They are often flashes in the pan--they start off strong, leveraging a brilliant product or a groundbreaking marketing approach; then they taper off, because they have no idea what to do after the "brilliant" and "groundbreaking" tactics run their course. On the other hand, the businesses that sustain their success over the long term have been able to develop a multifaceted picture of what they want to be. And they use that three-dimensional picture as a guide to move from where they are today to where they want to be in the future.
As individuals, many of us follow a career path built on tactical decisions made in isolation, without a broader context. We find ourselves lurching from one priority to the next. All of the facets of the life we want to have--salary, job title, house, social activities, intellectual pursuits, role in the community--are tactical. Figuring out how all those facets fit together is a strategy. Or, as Howard would say, it's business planning for your life's work.
"To undertake business planning for your own life," Howard explained to me, "you need to start at the strategic level. Develop an overall image of where you want to end up. And I don't mean the title you want at the height of your career or the position you hope to have eventually. Develop the strategic vision and then make decisions--respond to inflection points--in ways that make sense and that help you realize that image."
The first step in defining your legacy is to realize that it is a conscious choice: you have the ability to shape who it is that you become over your lifetime, to shape the nature and path of your career in the context of your life. Once you accept the power to choose, there are myriad ways to engage in that all-important "deep think."
I particularly like the approach that Howard once suggested: think about what you want people to say at your funeral. Consider how you'd want those you care about to describe you--on the most personal levels, separate from the structures and roles that define you to the rest of the world. Envision what you'd want your children to say when they describe you to their children. Or think about it this way: if a camera could take a "legacy" snapshot of you in the moment before you departed the earth, what do you want that picture to show?
The most fulfilled people I've met--both those with enormous wealth and those without--answer this question in personal terms that go beyond traditional career success. "I want my tombstone to read 'He was a friend to the world,'" the former chairman of the world's largest hotel company once told me. "I hope my legacy will be the individual girls whose lives I've changed by helping them learn to read," explained an extremely successful Turkish entrepreneur. And Bill Gates, speaking to Harvard graduates a few years ago, noted that he wants to be remembered not primarily for revolutionizing the personal computer industry, but for having played a small role in alleviating disease for the people of Africa. Each of them--and many others who have taken the time to draw a picture of their future lives and paths--have a broad, three-dimensional vision of themselves, of which professional and financial success is but a single element.
For them, legacy is not just a theoretical construct; it is a practical, highly effective tool that guides the major choices they make in their careers and their lives.
Excerpted from Howard's Gift: Uncommon Wisdom to Inspire Your Life's Work  by Eric Sinoway with Merrill Meadow. Copyright (c) 2012 by Eric Sinoway. All rights reserved. Reprinted with permission.
[Image: Flickr user Kate Hannon ]