Some years ago, during the George W. Bush administration, I was introduced to a man named Richard at a leadership conference. Richard was a business manager for artists, writers, and musicians. Several mutual acquaintances had told me Richard and I had much in common. He lived in New York City, where I had just bought an apartment, and we agreed to get together for dinner the next time I was in town. At the last minute, he bailed out for no apparent reason. Oh well.

A few years later—during the Obama administration—we finally got together for dinner and, as friends had predicted, immediately hit it off. Lots of spirited discussion and laughs. At some point Richard expressed contrition about canceling on me way back when, imagining all the good times and jovial meals we’d missed out on during, as he put it, those “wasted years” before we met. He was joking about the “wasted years,” of course, but he couldn’t conceal a shade of melancholy, as if he had bungled a life decision that required an apology.

He’d periodically repeat that note of contrition the two or three times a year we’d get together in New York. Each time, I’d say, “Let it go. I accept your apology.” Then, during one of our dinners, he told me a story.

He had just graduated from high school in a Maryland suburb. An indifferent student and not yet interested in college, he enlisted in the U.S. Army. After three years of service, at a military base in Germany rather than in combat deployment to Vietnam, he returned to Maryland, determined to get a college degree. He was twenty-one and finally clear-eyed about his future. He spent the summer before his freshman year driving a cab around the Washington, D.C., area. One day his fare from the airport to Bethesda was a young woman, a student at Brown returning from a year of study abroad in Germany.

“We had an hour in traffic to compare notes about Germany,” Richard explained. “It was one of the most charming hours of my life up to that point. There was definitely chemistry in that cab. When we pulled up to her parents’ very large house I carried her bags to the porch, stalling so I could figure out my next move. I wanted to see her again, but a driver asking a passenger out on a date was frowned upon, so I did the next best thing. I wrote my name on a taxi company card and smoothly said, ‘If you need a ride to the airport, call the dispatcher and ask for me.’

“She said, ‘I’d like that,’ making it sound like we were already agreeing on a date. I floated back to the cab, high on the possibilities. She knew how to reach me and I knew where she lived; we were connected in some small way.”

As Richard spoke, I was sure I knew where his story was going. It was the raw material for nearly every romantic comedy I’d ever seen. Girl and boy meet, one of them loses a name or number or address, the other waits in vain to hear from them again, by happenstance they run into each other years later and reconnect. Or some variation thereof.

“She called a few days later and we set up a date the next weekend,” Richard continued. “I drove to her house and stopped three blocks away to collect myself. This evening was important to me. I could see spending my life with her, despite the fact that she came from a much more well-to-do background than mine. And then I did something inexplicable. I froze. Maybe it was the big house or the swanky neighborhood or the fact that I drove a cab, but I couldn’t work up the courage to walk up to her door. I never saw her again—and my cowardice has haunted me for forty years. It has to be a big reason why I’ve spent my entire adult life alone.”

Richard’s voice choked up with this abrupt and baffling ending to his story. His face was so anguished, I had to look away. I had expected either a heartwarming reminiscence about a successful first date and many more to follow, or a bittersweet admission that after a few dates he and the young woman realized they weren’t the soulmates they had hoped they were. Instead, I had heard a narrative of colossal regret, that empty and most desolate of human emotions. It was a conversation stopper that landed between us with a tragic thud. I had nothing healing or redemptive to add. Regret is a feeling I wouldn’t wish on any human being.

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Any decent advice book aims to help readers overcome a perennial challenge. Losing weight, getting rich, and finding love are three universal challenges that come to mind. The focus in my recent books has been on our behavior at the nexus where our professional aspirations intersect with our personal well-being. In What Got You Here Won’t Get You There, I tackled how to eradicate self-defeating behavior in the workplace; in Mojo, how to deal with career setbacks that stop our momentum; and in Triggers, how to recognize the everyday situations that trigger our least appealing responses and choices.

The challenge we’re tackling here is regret.

My premise is that our lives toggle back and forth between two emotional polarities. At one pole is the emotion we know as “fulfillment.” We judge our internal sense of fulfillment against six factors that I call the Fulfillers:

• Purpose

• Meaning

• Achievement

• Relationships

• Engagement

• Happiness

These are the guideposts that dictate all our striving in life.[*1] We invest enormous resources of time and energy to find purpose and meaning in our lives, to be recognized for our achievement, to maintain our relationships, to be engaged in whatever we do, and to be happy. Our vigilance and striving here are unceasing, because our connection to these six factors is fragile, fickle, and fleeting.

Happiness, for example, is the universal temperature reading of our emotional well-being, which is why we frequently ask ourselves whether we’re happy, or endure the question from others. Yet happiness can be our least permanent emotional state, as brief as a dream. Our nose itches, we scratch it, we’re relieved and happy, then we notice an annoying fly buzzing around the room and a chilly breeze gusting through the window, and somewhere a leaky faucet is dripping. This goes on from moment to moment all day long. Our happiness vanishes instantly and constantly. Meaning, purpose, engagement, relationships, and achievement are equally vulnerable. We reach for them and grasp them, but with alarming rapidity they slip through our fingers.

We think that if we can create an equivalence between (a) the choices, risks, and effort we made in pursuing the six Fulfillers and (b) the reward we received for doing so, we will achieve a lasting sense of fulfillment—as if we’ve discovered that our world is fair and just. We remind ourselves, I wanted it, I worked for it, and my reward was equal to my effort. In other words, I earned it. It is a simple dynamic that describes much of our striving in life. But as we shall see, it offers us an incomplete picture of an earned life.

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Regret is the polar opposite of fulfillment.

Regret, in the words of Kathryn Schulz in her wonderful 2011 TED talk on the subject, is “the emotion we experience when we think that our present situation could be better or happier if we had done something different in the past.” Regret is a devilish cocktail of agency (our regrets are ours to create, they’re not foisted upon us by others) and imagination (we have to visualize making a different choice in our past that delivers a more appealing outcome now). Regret is totally within our control, at least in terms of how often we invite it into our lives and how long we let it stick around. Do we choose to be tortured or bewildered by it forever (as in the case of my friend Richard), or can we move on, knowing that regret is not finished with us, that we will surely live to regret again someday?

Our regrets are not one-size-fits-all. Like men’s shirts, they come in S, M, L, XL, XXL, and even bigger. To be clear, in this book I’m not going to be concerning myself with microregrets, incidental missteps such as the slip of the tongue that offends a colleague. These are regrettable faux pas usually resolved with a sincere apology. Nor am I thinking about our medium-sized regrets such as the tattoo that inspired Kathryn Schulz’s TED talk, tormenting her the moment she left the tattoo parlor, obsessively wondering, “What was I thinking?” Eventually she got over it, even gleaned a lesson about how “exposed” and “totally uninsured” she was from her regrettable choices—and promised herself to do better in the future.

What we’re addressing here is supersized existential regret, the kind that reroutes destinies and persecutes our memory for decades. Existential regret is deciding not to have children, then changing our mind too late. It’s allowing our soulmate to become “the one who got away.” It’s turning down the perfect job because we doubt ourselves far more than do the folks who want to hire us. It’s not taking our studies seriously in school. It’s looking back in retirement and wishing we’d allowed ourselves more leisure time to develop interests outside work.

It can be hard but it’s not impossible to avoid existential regret—as long we’re open to focusing on our fulfillment. Being open to opportunities that come our way can help us avoid regret, even when we believe we’re already happy and fulfilled where we are. The simplest tool I know to finding fulfillment is being open to fulfillment.

Readers of my previous books know that I am incapable of concealing my admiration for my friend Alan Mulally. I consider Alan a role model for creating a life blessed with fulfillment and zero regret.

In 2006, when Alan was CEO of Boeing Commercial Airplanes and was offered the CEO job at Ford Motor Company, he sought my advice about the pros and cons of leaving Boeing, the only company he’d ever worked for. As his former coach, I felt I was in a uniquely objective position to advise him. I knew that he was an exceptional leader and believed he could succeed in any executive role. I also had known for some time that he would be given multiple opportunities to lead at other companies, although very few of them would be sufficiently appealing or challenging to lure him away from Boeing. Any offer would have to be an extraordinary opportunity to serve. Helping revive Ford was such an opportunity, and I reminded Alan of previous career advice I’d given to him: Be open.

Alan initially declined the Ford offer. But he kept an open mind and continued to gather information about what would be required to reinvigorate the auto giant, reconsidering the job from all sides (it’s one of his talents). A few days later, he accepted the offer to serve at Ford. In doing so, he continued to focus on being open to achieving even greater fulfillment, not avoiding regret.[*2]

Regret, however, is our secondary theme here. I flirted with titling this book “The Regret Cure” but concluded that that would be misleading. Regret is the stranger knocking on the door, appearing when we make poor choices and everything has gone awry. It is the thing to avoid, keeping in mind that we cannot banish it entirely (nor should we, considering how instructive our regrets can be: “Note to self: Don’t do that again!”). Our official policy on regret in these pages is to accept its inevitability but reduce its frequency. Regret is the depressing counterweight to finding fulfillment in a complex world. Our primary theme is achieving a life of fulfillment—what I call an earned life.

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One of our guiding concepts here is that our lives reside on a continuum that roams between Regret and Fulfillment, as illustrated below.

Given the choice, each of us I’m sure would prefer spending more time approaching the right extreme here than the left. In researching this book, I asked a wide variety of people in my professional circle to locate themselves on this continuum. It’s hardly a rigorous scientific study, but I was curious about what propelled people to place themselves closer to fulfillment than regret, and if so, how close. My respondents were all successful by the obvious metrics we rely on. They were healthy. They had accumulated a credible list of professional achievements, as well as the status, money, and respect that tend to accompany achievement. I figured most of them would come very close to the extreme right of the line; all the signs said they should be experiencing near-total fulfillment.

Silly me. The truth is, none of us knows the scale of another man or woman’s aspirations and therefore none of us knows the depth of his or her disappointments and regrets. We can neither presume nor predict other people’s relationship to fulfillment or regret, even those we think we know well. Here is the response of a European CEO named Gunther who’s at the top of his field and yet overwhelmed by regret for neglecting his family in favor of his career:

Pressed to measure his sense of fulfillment, Gunther saw that all the conventional metrics of success at which he excelled could not counteract his sense of failure as a parent and husband. The failure overwhelmed his success, as if he’d wasted his life earning the wrong rewards.

It was the same story with my coaching client Aarin. I regarded her as a roaring overachiever—and therefore an amply satisfied woman with few regrets. Aarin had emigrated from Nigeria to the United States at age eleven, earned an advanced degree in civil engineering, and developed a specific expertise that made her an in-demand consultant in the construction of skyscrapers, bridges, tunnels, and other big structures. She was in her early fifties, happily married, with two college-age children. As an African immigrant, she was a rarity in her line of work, possibly the only one, which meant that she had basically invented a career for herself. I admired that. I’d been coaching her for six years under the impression that I knew both her dreams and resentments. So her relatively downbeat response surprised me.

How could she, of all people, be more regretful than fulfilled? She had a “baseline satisfaction” with her life, she said. “I have no reason to complain.” And yet she was swamped by regret. Her regrets centered not on how far she’d come but rather on how little she’d done compared with what she believed she could be doing. No matter what she did, she couldn’t shake the thought that she was falling short of her potential. She regretted that when she took on a project that paid well enough to cover overhead and salaries, she tended to coast and ease up on chasing new business. Why, she wondered, didn’t she hire people to handle multiple projects at the same time and give herself more time for rainmaking? “Everyone thinks I’m this hard-charger,” she said. “But I’m actually a sheep in Type A clothing. Most days I feel like an impostor, unworthy of the fees I’m charging and the praise I receive, always dreading the moment when I’ll be found out.”

Clearly, we had more coaching to do.

I was surprised when any of the responses in my admittedly arbitrary and unscientific survey resembled Gunther’s and Aarin’s answers. People who could be seen as paragons of fulfillment turned out to be tormented by persistent regret.

I expected all of them to be like Leonard, a Wall Street trader who’d been forced into retirement at age forty-six when his type of highly leveraged trading became a casualty of the Dodd-Frank financial reforms of 2009. Here’s Leonard’s response:

I would have wagered that Leonard would be bitter about the premature end to his career—and that his bitterness would translate into profound regret. Apparently not. I asked him how he could feel this way, given how young he was and how much more he could have accomplished.

He said, “I’m a lucky man. A statistics professor told me that I had a small gift. I could see rates of change in yields and interest rates in my head. So I went into bond trading, the one field where I could get paid for my small talent. I ended up at a firm with a compensation scheme that was pure pay-for-play. If I made a profit, my share was contractually spelled out to the penny. If I didn’t, I was out. I made money every year and I never felt underpaid or cheated. I got exactly what I deserved, and thus it felt fully earned. That’s not only satisfying when I look back on it; it’s gratifying because I still have the money.” He was laughing when he said this, clearly astonished by his good fortune and also delighted.

His rationale disarmed me. For years I had maintained a prejudice about Wall Street types, believing they were smart people who went into the financial sector grudgingly, not because they were fascinated by markets but because it was an easy way to make a pile of money, get out early, and spend the rest of their lives doing what they really wanted to do. They were willing to sacrifice their best years doing something lucrative that they didn’t necessarily love so they could achieve independence and comfort at the end. He showed me I was wrong. He loved trading securities. It came easily to him, which increased his chances of being demonstrably excellent at it. The fact that he was in a field that paid very well for excellent performance wasn’t a reward as such; it was a means to an end. Fulfillment to him came from the validation of being a star at his job and, as a result, being a good provider for his family. I asked him to grade himself on the six Fulfillers as if I were a doctor conducting an annual physical. Each category was under his control. He had always been aiming for financial security so he could provide for his immediate as well as extended family, which checked off purpose, achievement, and meaning. His engagement had been total, “perhaps excessive,” he allowed. He loved trading. His relationships with his wife and grown children were solid. “I’m perpetually amazed my kids still want to spend time with me,” he said. Ten years after leaving the trading desk, he was giving away a healthy portion of his fortune and repurposing his professional expertise by providing pro bono financial advice. I didn’t bother asking him if he was happy. The answer was written on his face.

Red Hayes, the man who wrote the 1950s country music classic “Satisfied Mind,” explained that the idea for the song came from his father-in-law, who one day asked him who he thought the richest man in the world was. Red ventured a few names. His father-in-law said, “You’re wrong; it is the man with a satisfied mind.”

In Leonard, I realized, I had found a rich man with a satisfied mind—someone who had maximized fulfillment, minimized regret. How does this happen?

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This is our operative definition of an earned life:

We are living an earned life when the choices, risks, and effort we make in each moment align with an overarching purpose in our lives, regardless of the eventual outcome.

The pesky phrase in that definition is the last one, “regardless of the eventual outcome.” It goes against much of what we’re taught about goal achievement—setting a target, working hard, earning our reward—in modern society.

Each of us knows deep in our heart when any success, major or minor, is merited and when it’s a product of a merciful universe taking pity on us for a moment. And we also know the different emotions each result elicits.

Merited success feels inevitable and just, with a tinge of relief that we weren’t cheated out of our win by a last-second calamity.

Unmerited success is all relief and wonder at first, the squidgy guilt of being the beneficiary of dumb luck. It’s a cloudy, not wholly gratifying feeling—a sheepish sigh rather than a triumphant fist pump. Which explains why, with the passage of time, we so often revise history in our minds, turning our dumb luck into something we actually earned through the application of skill and hard work. We find ourselves standing on third base and insist we hit a triple, when in fact it was a fielder’s error that got us from first to third. We play this revisionist mind game to mask the illegitimacy of our “success,” proving again E. B. White’s trenchant observation that “luck is not something you can mention in the presence of self-made men.”

By contrast, something truly earned makes three simple requirements of us:

• We make our best choice supported by the facts and the clarity of our goals. In other words, we know what we want and how far we need to go.

• We accept the risk involved.

• We put out maximum effort.

The deliverable from this magical brew of choice, risk, and maximal effort is the glorious notion of “an earned reward.” It’s a perfectly valid term—as far as it goes. An earned reward is the ideal solution to every goal we pursue and every desirable behavior we try to perfect in ourselves. We are said to “earn” an income, and a college degree, and other people’s trust. We must earn our physical fitness. We must earn respect; it is not given to us freely. And so on with the long menu of human striving: from a corner office to the affection of our children to a good night’s sleep to our reputation and character, all must be earned via choice, risk, and maximal effort. This is why we valorize the merited success; there’s something heroic about applying maximum energy, wit, and will to get what we think we want.

But an earned reward, no matter how heroic, does not go far enough for my purposes. It certainly didn’t help Gunther, the European CEO, feel fulfilled. His entire career was an unbroken succession of earned rewards—of ever greater goals pursued and achieved. But all those earned rewards occurred at work, not at home. They had no power to prevent him from being overwhelmed with regret about his failed family life. They certainly didn’t add up to an earned life. Aarin, as well, did not find satisfaction in her impressive string of achievements. Each big win seems to have left her questioning her motivation and commitment: She could have, and should have, tried harder.

In many cases, the outcomes of our choices, risks, and maximal efforts are not “fair and just.” Unless you’ve led an absurdly charmed life, you know that life is not always fair. It starts at birth: who your parents are, where you grow up, your educational opportunities, and so many other factors, most of them beyond your control. Some of us draw the silver spoon, some the lump of coal. In some cases, the disadvantages we inherit can be overcome through shrewd decisions and maximum effort. Even then, life’s inequities can bite, e.g. you’re the perfect job candidate but somebody’s nephew gets hired instead. You can do everything right, but there’s no guarantee the outcome will be just and fair to you. You can be bitter and angry, whining “It isn’t fair.” Or you can accept life’s disappointments with grace. Just don’t expect every attempt to “earn” a goal to deliver the appropriate reward. The payoff is not as reliable as you wish or deserve.

There’s another, more damning reason I hesitate to put too much faith in the concept of an earned reward—namely, that it’s too impermanent and fragile a vessel to contain our wishes and desires for an earned life. The emotional lift we get from an earned reward is fleeting. Happiness leaks out of us from the first second we’re aware of it. We get a long-sought promotion, and with alarming haste we raise our sights to the next rung on the ladder, as if we’re already dissatisfied with what we worked so hard to earn. We campaign for months to win an election, then, after a quick celebration, immediately have to get to work for the voters. The striving is over; a new striving begins. Whatever prize we have earned—a big raise, a partnership, an ecstatic review—our victory dance is brief. Our sense of fulfillment and happiness simply doesn’t last.

I’m not denigrating the value of an earned reward—and all the energy that went into creating it. Setting goals and earning the desired outcomes are essential first steps for success at anything. I’m questioning their utility in achieving an earned life when they are estranged from a greater purpose in our lives.

This is why Leonard the Wall Street trader felt a sense of fulfillment in his life where others, perhaps more fortunate and accomplished than he, fell short. He wasn’t in the money game merely to make money. His striving was grounded in the higher purpose of protecting and providing for his family. An earned reward not connected to a higher purpose is a hollow achievement—like a basketball player who’s interested only in maintaining his high scoring average rather than making the myriad sacrifices (e.g. taking a charge, diving for loose balls, guarding the opponent’s best player) that win close games and championships.

In these pages, we will see that an earned life makes only a few demands of us:

• Live your own life, not someone else’s version of it.

• Commit yourself to “earning” every day. Make it a habit.

• Attach your earning moments to something greater than mere personal ambition.

In the end, an earned life doesn’t include a trophy ceremony. The reward of living an earned life is being engaged in the process of constantly earning such a life.

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This book was written during the COVID pandemic, while I was isolated with my wife, Lyda, in a one-bedroom rental along the Pacific Ocean in southern California. We had just sold our home of thirty years in Rancho Santa Fe, north of San Diego, and were waiting in the apartment to make a permanent move to Nashville, where our twin grandchildren, Avery and Austin, live. We waited fifteen months to move out.

Unlike my other writing, this book is inspired not only by the lives of my coaching clients, using their examples as source material, but also by my own. It’s written at a moment in my life when I still haven’t done all I want to do, but I’m running out of time. So I have to make choices. I have to let go of dreams I entertained in my younger days, not solely because the clock is ticking but also because those dreams don’t make sense to me anymore.

This book is a reflection on my future. I’ve learned it’s never too late to reflect, because as long as you’re breathing, you have more time. But it’s never too early either—and early is better. That’s what I hope, you the reader, whatever your age, take away from these pages as you reflect on the life you’re shaping for yourself and make choices based on that reflection. There is a lot of soul-searching here about people who helped me and what they taught me. There’s a lot of soul-searching because of the pandemic, which turned out to be an extraordinary eighteen months of nonmonetary “earning” for me. There’s also a lot of soul-searching because I’m at a stage of life when the opportunities to confront existential regret increase predictably—for the simple reason that the ten- or twenty-year intervals into the future that may have dictated my choices in earlier days, when time seemed limitless, are no longer a rational option for me. I may live thirty more years and reach one hundred. But I can’t count on that, nor do I know whether my good health will continue or which friends and colleagues will be around to notice. As my time on earth gets shorter, I have to conduct triage with all the unchecked boxes on my life list. Which items are not doable? Which items no longer seem so important? Which two or three items are absolute musts that I’ll seriously regret not achieving? I want to use my remaining time to maximize fulfillment and minimize my regrets.

This book is one of my absolute musts. I hope it serves you well, teaching you to use your time providentially and to finish with no regrets.