Starting at the End

Eric Sinoway

I suggested to him that, in at least a couple of respects, his was a normal reaction. It’s hard to find the same energy working for someone else after you’ve been the top dog. There’s also an understandable letdown— a sense of lost momentum— when you’ve brought a major career goal to fruition, and done so much earlier than you’d dreamed possible. Yes, George said, he understood that those things had dampened his enthusiasm, but he felt that he’d come to terms with them. He’d even accepted that it was time to walk away from the company he had built, which was a doubly difficult decision because the challenge of ensuring the livelihood of his “work family”— his longtime employees— had been a powerful and positive motivator for him.

All the questions I was raising were about the past, George explained, and the past wasn’t the problem: the future was. He’d considered a series of new entrepreneurial ventures, but none felt right. He’d been in discussions about joining a consulting firm, only to back away at the last minute. Now he was even considering going to law school; he didn’t particularly want to practice law, but at least it would give him a clear path and goal for a few years.

“Here’s a guy who’s fulfilled his career goals years ahead of what he’d originally anticipated,” I explained to Howard, “and now he’s dragging around in circles, unable to chart a new direction.

He’s a really driven person, full of energy— but he can’t figure out where to direct that energy, going forward. Watching him today was like seeing an overheating boiler getting ready to explode.” Howard sat silently. I swallowed a couple bites of the sandwich, then continued. “He can’t even enjoy the nonwork activities in his life. He’s bored playing golf; he stopped going to the theater; and he’s probably going to quit the community organization boards he’s on.”

“Really?” said Howard, the first word he’d spoken since I started telling the story.

“Yeah. It was a very depressing conversation,” I said. Howard thought for a bit, then threw out a series of questions that surprised me because— at that moment— they seemed so beside the point. Question: Did I know if George played a lot of golf in college or early in his career? (Answer: It was something George picked up later. When I knew him in the early years, he loved bowling. The game bored me silly, but he got such a kick out of it that I let him drag me out to the lanes a couple times.) Question: What were the community organizations George was involved with? (Answer: One was a local arts center, and the other was the American Lung Association.) Question: Is George an artist himself ? Does someone in his family have lung disease? (Answer to both: No, I don’t think so.)

After answering Howard’s questions, I threw one back at him: “What the heck’s all that got to do with his next career move?” “Everything,” he said, then stood up and disappeared into his den. He returned carrying a large plastic shopping bag filled with games and toys destined for his grandkids. He rummaged through it until he found what he wanted: a big jigsaw- puzzle box.

“My granddaughter loves these things,” Howard said. “She’s got this intuitive understanding of how to work them. Starts by forming the outside edges of the picture, then moves inward. She’s creating a basic frame— a context— to use in making decisions about how to fit the rest of the pieces together.”

“A strategic thinker at age ten,” I said. “I guess she takes after her grandmother, huh?”

He smirked but otherwise ignored my jibe. “Clearly, this young success— George—has hit a major inflection point in his career and his life. And just as you can leverage a negative inflection point into a beneficial opportunity, a positive inflection point can become a real pain in the ass if you don’t handle it well.” He let that sink in for a moment before continuing.

“Remember when we talked about those astronauts who used the moon’s gravity as an inflection point to get back home?”

“Sure,” I mumbled as I worked on the second roast beef sandwich. “Well, inflection points aren’t very useful without a context, without a sense of how you want to use them. If Apollo 13’s astronauts hadn’t known exactly where they were relative to where they wanted to end up, their risky maneuver around the moon would have been a joyride to oblivion. Without knowing their desired end point, they wouldn’t have been able to decide how fast they needed to go, how long to burn the engine, when to shut it down— any of that.

“Those astronauts actually had it easy, in a certain way,” Howard continued. “They had one single objective on which everything depended. There was no ambiguity, no weighing of alternative places to go. They needed to get to one place—Earth—and quickly, before they got cooked. But here on terrafirma, things are more complicated because we don’t have that same kind of precise, singular goal for our life’s work.”

He shook the jigsaw box, and the puzzle pieces rattled around inside. “There are a whole lot of jigsaw pieces in anyone’s life and career. But how do you know which piece to grab next if you don’t know what the overall picture’s supposed to look like— if you don’t at least have a framework to consider?”

“So George has been handed a big new stack of jigsaw pieces, with no idea how to put them together,” I said. Howard nodded, and I continued, thinking out loud, “He’s a driven guy. Except without a direction, without even a compass to say which direction is which, he’s driving himself crazy.”

“Bingo!” he said, grabbing my now empty plate and bringing it over to the counter.

Well fed, and assuming our conversation about George was done, I began to pull my notebook and a few files from my briefcase. Yet when Howard came back to the table— with an enormous slice of peach pie and a glass of milk, and a look on his face that said, “Don’t argue; just eat this”— it became clear that his mind was still on George’s situation.

“What was that old saying? ‘If you don’t know where you’re going, any road will take you there,’ he said. “It may be false nostalgia, but I think people used to give a lot more thought to the broader context of the big decisions they make about their lives. Not so much anymore, it seems.”

I had to smile, because talking with Howard like this made me feel like a student again, a student privileged to get one-on one tutoring from one of Harvard’s great minds.

“Maybe it’s an unanticipated side effect of our hyperconnected, twenty- four/seven culture,” I offered. “Life seems to be happening so quickly and so continuously that people are unaccustomed to taking time to think. And they’re reluctant to ‘waste time’ thinking, instead of acting. This reminds me of something one of my business partners, Mike Wargotz, says, ‘Hurry up and fail.’ ”

“You’re probably on target,” Howard said, “but it’s a really counterproductive situation. Nine times out of ten, a person will lose time and waste energy if she just heads out to accomplish something without first considering why she’s pursuing it and what success would look like.” As I ate my pie, Howard continued.

“You know, Eric, I think there’s another factor at work, too,” he suggested. “In this hyperconnected society of ours, there’s a huge emphasis on what I call ‘celebrity success’ culture: we increasingly equate being well known with success, and we turn successful people into celebrities. All this ‘success’ pervading our cultural atmosphere leaves people with two internalized assumptions. “First, we believe we’re all equally worthy of and prepared for success. You know, the alternative— having to admit that maybe we’re not good enough to succeed at a particular thing we want to succeed at— is too painful for many people to even consider. Second, we just assume that everything must work out.”

“You mean, we assume that it’s life’s responsibility to point the way for us?” I asked.

Howard nodded and paused as his mind reached out for just the right analogy. “It’s as if many people think their lives come equipped with a personal GPS that shows the best career on-ramps and off-ramps—at the push of a button. Unfortunately, even the best GPS doesn’t tell you where to go, only how to get to the specific place you’ve set as your destination.

“Ironically, it’s often the folks who consider themselves smart or talented or hardworking who fall into that logical fallacy—because they figure their brains, talent, or diligence will automatically make clear how fast to go and what turns to take, even without their having first determined their goal.”

We both considered that for a moment, then he motioned for us to head into the den. I didn’t even bring my files with me: class was definitely still in session. Howard sat back on the couch, put his feet up on the coffee table, and continued on an intellectual path clearly laid out in his head. “Eric, I can’t tell you how many of my students try to construct the puzzle of their careers by identifying a few desirable pieces and building on those. Or, worse, they just go with the pieces they find in their hands,” he said. “But a meaningful, satisfying life consists of the entire puzzle. It takes real thought to design and time to build. So when a person pursues one piece of their career and life puzzle predominately and without forethought— without regard for how it fits into a broader picture— trouble follows.” I knew that over the years, Howard had met many “successful” people who were miserably unhappy despite their very active lives, fancy titles, expensive cars, and vacation places in the mountains. I’d had innumerable similar experiences. These people excelled on the dimension of success measured by wealth, status, organizational authority, or some other narrow criteria. Yet they hadn’t taken the time to understand how that dimension should fit into the more complex, long- term picture of their lives. They’d never considered how the primary goal they were pursuing should fit with other objectives— ones that might have been smaller- scale but were nevertheless important. Indeed, they hadn’t recognized that ignoring the rest of the picture often comes at a significant emotional cost.

“To use a different analogy,” Howard explained, “focusing almost exclusively on one goal is like exercising a single muscle: your overall health doesn’t improve; in fact, it’s pretty unhealthy. And it sounds like that’s exactly what your friend George has done; all his planning and most of the energy he expends have been focused on one piece of his life’s puzzle.” Now, here was a point I didn’t get. While George hadn’t necessarily charted out a lifelong career vision, he had built what seemed to me to be a pretty well- rounded life so far. Sure, he worked hard. But he also spent lots of time with his family, regularly engaged in a sport he enjoyed, participated in cultural activities, and was involved in his community. I had to assume that these things all brought him pleasure and enriched his life; that they were all integral to how he defined himself. In fact, that was one reason I was so unsettled by George’s experience: he wasn’t just dissatisfied with his career situation, he was unhappy with most aspects of his life—displeased with everything, it seemed, except his family.

So I pushed back on Howard’s point. “It seems to me that he did have a multidimensional life,” I said. “Career, family, social activities, community work— and that this one positive change has somehow unbalanced it.”

Howard smiled impishly, as if he’d lured me into a trap on the chessboard—a trap he now sprung. “Ah yes, all his social activities, his community engagement, his golf. . . . On the surface, sure, his life looks well- rounded—three-dimensional, if you will. But I’d be willing to bet a platterful of roast beef sandwiches that his life was, in fact, ‘pseudo three- D.’ ”

I burst out laughing at yet another Howard- ism. “A ‘pseudo three- D’ life? What the heck’s that mean?”

“It means that all of it was— whether he knew it or not— part of his strategy for pursuing financial success, not distinct elements of a well- rounded life. An extension of one dimension that appears to be multifaceted—three- dimensional—but really isn’t. Pseudo three- D.”

I began to follow. Howard was suggesting that George hadn’t taken up golf because he really liked it; nor gone to the symphony because he loved classical music; nor accepted leadership roles at the art center or with the Lung Association because he was passionate about the organizations’ missions. He engaged in those activities because they were perfect ways to connect with people— like corporate executives, bankers, investors, and others— who could help his business grow.

Maybe it was a conscious strategy. More likely, given his present degree of confusion and frustration, it was just an intuitive process of leveraging connections. Without intending to do so— and without making explicit choices about the trade-offs—he had built an interconnected web of business relationships, community engagement, and social activities that defined his life beyond the family. But with one hugely positive turn of events, the whole structure became almost pointless. Professionally and— to a certain extent—psychologically, George had found himself at a new beginning. And he was clueless about how to start over, because he didn’t fully understand how he’d gotten there in the first place.

“Don’t misunderstand, Eric; I actually admire George for what he’s done, for the sacrifices he’s made for his real ‘life goal.’” I looked at him with a quizzical expression, and he explained, “I’m suggesting that financial security wasn’t George’s ultimate goal, but only a means to an end. I honestly think his real life goal has been more fundamental: protecting and nurturing his family—both his at-home family and the family he created in his company. Getting rich and all the steps involved in it were just elements of his all- consuming strategy for accomplishing that goal.”

I absorbed this analysis for a moment, then suggested, “So now he needs to refocus. He should acknowledge ‘protecting and nurturing my family’ as his primary goal, then take a fresh look at what that means, given his new financial reality. Because financial support is only one facet of ‘protecting and nurturing,’ and it’s important that he consciously acknowledge the other facets—emotional, intellectual, spiritual, social . . .” Howard nodded vigorously, and I continued. “More than that, he should explicitly give himself permission to consider what other things are important to him— what will give him joy, give him a sense of personal engagement in things that are meaningful, give him a sense of satisfaction.”

“Exactly,” Howard said. “Now that he’s got some time to spare, he should just stop for a bit. Tell him to stop driving hard and fast to find the next thing. Tell him to take time to think, broadly and deeply; to consider all the individual elements of who he is and what he wants in his life—large and small—and how they might relate to one another.”
“Going back to your puzzle analogy,” I offered, “he should create a solid frame around his life, a clear picture that will be the basis for responding effectively to this huge inflection point in his life.”

“Yes, he should create a clear context for his decisions,” he replied. “But I’m not talking about a rigid, permanent framework. It needs to be an evolving, flexible structure that enables him to have a holistic view of his future life and how day- today work and personal activities should fit into it."

“Why evolving and flexible?” I asked.

“Because our lives are flexible and evolving. The framework that you develop today will certainly inform your framework a year from now. But the very act of responding to an inflection point today will change the way you view your life tomorrow.” He pointed at a beautiful chess set sitting on a shelf behind him. “It’s much like a game of chess: once you’ve gotten a few moves into it, every subsequent move can change the entire complexion of the game. The most innocuous move can have huge long- term impact, and you want to be able to look at the way things are now, not just how they were before the last move. Good chess players understand that— and so should each of us when we’re thinking about our careers.

“The problem is that many people make the mistake of assuming their perspectives never shift as their careers and lives evolve— as they move closer to or slide further away from what they had previously determined were their long- term goals and hopes. They fall into the trap of not asking simple questions, like: ‘Do I really want the same things today that I wanted last year?’ ‘Are the reasons I took this job five years ago still valid now?’ ‘Are the decision points I used to make my last choice the right ones to use in my next one?’ ”

“In other words,” I said, “don’t respond to the last inflection point. Focus on leveraging this particular inflection point in front of you at this particular point in time, based on today’s perspective of what you want in your life, not yesterday’s. Or, to quote a great sage: live life forward.”

He chuckled at my use of his favorite phrase and said, “You got it.”

“Okay, then George is in the perfect situation, because whatever framework he had before has been blown up— that much I’m sure he gets. But what does he do to construct this renewed picture? We assume that ‘protect and nurture the family’ is going to be a big piece of it, but where does he go from there? How should he start to frame the picture of what his future should be?” At my question, Howard smiled brightly. “He should start at the end.”

“Come again?”

“You heard me: start at the end. George should start by thinking about what he wants his life to have looked like when it’s over. He’s made a bunch of money. Great. But what’s his legacy going to be? Looking long term, legacy is what we should all be thinking about. The earlier you think about it, the easier it will be to identify the path to get there—and the happier you’ll be throughout your life.

“ ‘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,” he continued. “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.

About the Author

From Howard’s Gift by Eric Sinoway. Copyright © 2012 by the author and reprinted by permission of St. Martin’s Press, LLC.