1. Is it Achievable?

Do I believe I can attain it?

The early twentieth-century author Neville Goddard said, “The drama of life is a psychological one and the whole of it is written and produced by your assumptions. Your assumption guides all of your conscious and subconscious movements so inevitably that it actually dictates events.”⁷ Wistfully thinking “That would be nice …” often signals we don’t think a goal is possible and, therefore, won’t be. If, instead, we are optimistic, saying, “I am so happy I’ve achieved this” as if we already have, there is a kernel of belief that it is within reach. In the Explorer stage, you are asking, “Can I see myself doing or being this?”

Often though, there is a gap to bridge. Knowing that our assumptions guide our movement, how do we change our assumptions so “that would be nice” becomes “this is nice”? While it’s true that there are unattainable objectives, it is also true that there is a nearly limitless range of things that are possible. They require only that we believe, and act on our belief.

To quote Shakespeare again, “Assume a virtue if you have it not.” Four centuries later, we paraphrase, “Fake it ’til you make it.”

In 2000, Marcus Whitney moved to Nashville, Tennessee.⁸ He was a twenty-four-year-old dropout from the University of Virginia. “I had a one-year-old and another child on the way and was waiting tables six-and-a-half days a week,” he told me. His family was living in an efficiency hotel. “I didn’t have a lot of leeway or slack in my life.”

Whitney did, however, have a starting point, “When I was nine years old, my late Uncle Otis, who was a programmer at IBM, gave me a PC Jr.… I learned a programming language (BASIC) and the basic principles of how computers work.” As a child, he had envisioned himself as a programmer, so in his mind, a better life was possible.

But it had been fifteen years, and his computer skills were old and rusty. Still, Whitney started studying programming books between serving customers at restaurants. After working twelve-hour shifts, he’d put in another four hours on the computer at home. He applied for hundreds of jobs with little success. It wasn’t easy visualizing his goal, but “Having my back against the wall was helpful for removing a lot of extraneous narratives that weren’t helping me go where I wanted to go.” In his book, Create and Orchestrate, he describes how he got through the slowness of the Explorer phase:

There was more to it than just hard work. My mindset was critical.… There wasn’t a lot of evidence around me that I could be successful in making this transition. I had to create a mindstate supportive of my endeavor. I didn’t achieve that mindstate by believing I was becoming a programmer; I achieved that mindstate by believing I already was a programmer. This distinction is very important. By believing I already was a programmer, even though it wasn’t obvious to others, I bypassed many of the limiting thoughts and doubts about my ability to become a programmer. I never said I was a great or even a good programmer. I just believed I was a programmer. This small tweak of believing we already are what we want to be, rather than becoming it has significant downstream effects.⁹

Marcus Whitney’s first paid gig as a programmer was a barter deal. His wife needed a midwife, and the midwife needed a website, so services were exchanged. A year later, in 2001, Whitney got his first paid job as a programmer. In 2003, he was hired as the fifth employee at an email marketing company, later sold to a bigger firm. The founder, his former boss Clint Smith, remembers him well: “Marcus had the ability to play up a level or two—and ended up running all of engineering.”

Several startups, two exits, loads of desire, persistence, and twenty years later, Marcus Whitney is the founder of Jumpstart Nova, the first Black health-care venture fund in America. He’s the CEO of Health:Further, a health-care strategic advisory firm, and is cofounder and part owner of the Nashville Soccer Club, the major league soccer team in Tennessee.

If we are willing to do the hard work of changing our assumptions, we will begin to believe our goal is attainable.¹⁰ Belief is where an Explorer starts.

2. Is It Easy to Test?

Is there an easy way to test whether I want to be on this particular S Curve of Learning? If I decide to stay on this S Curve, will my initial pace be sustainable?

In 2019, I decided I wanted to be physically stronger. There were many options—I could join an Everest expedition, become a mixed martial arts/UFC fighter, or run. Setting aside the desirability and believability for a moment (you probably can’t picture me as a UFC fighter, either), how easily could I test if I wanted to jump to one of these physical fitness curves? Of the three, running is by far the easiest. I tested it by committing to run five minutes a day for a week, thirty seconds running and thirty seconds walking.

After a week’s exploration, I had enough information to know I wanted to be on a running S Curve, and I wanted to run at least one 5K. Now I had to decide on an initial pace for how quickly I would increase the time and distance I ran each day. Five minutes in week one, ten minutes in week two, up to fifteen minutes in week three? For me that was too ambitious. I was looking for sustainable, long-term behavior that would evolve from conscious and challenging to natural and automatic. I settled on small increments—a ten-second increase each time I ran. This was a manageable level of effort, to which my brain would say, I can do that! I did that yesterday! even on days when I wanted to just curl up in a chair with one of our cats.

It took about eighteen months to get to the top of my 5K S Curve, but because I made it easy enough to start and sustain, I persisted. I now run three times a week. The behavior has become automatic. I no longer think of running as something I do. It’s part of who I am. I am a runner.¹¹

Find simple and easy ways to test new S Curves of Learning. I know this sounds obvious, but I’ve found, both with myself and in coaching others, that once we feel inspired to do something new, we feel compelled to start really big. But when we need to make space on our cluttered mental and emotional shelves for something big, we find there’s little room. It’s discouraging. Where do we even start?

Start small. Set your initial expectations and incremental increases so small, so laughably small, that you deactivate your inner procrastinator. Each tiny benchmark is its own easy test. Is this S Curve feasible? Can I sustain this long term? Take baby, baby, baby steps.

Top management consultant Darrell Rigby knows early testing is essential to the success of any major innovation. Rigby’s fascination with innovation stems from his days at Harvard Business School. Rigby told me he was something of an oddity there—a “castoff,” in his words.¹² He went straight to business school after university without first paying his dues on the bottom rung of a company ladder, as many management students do before they matriculate. Landing a crucial summer internship would be a high hurdle for Rigby, and things weren’t looking good. He was dismissed as too young and inexperienced. Then he caught a break. “Bain decided to give me a chance,” Rigby said, referring to the now prestigious management consultancy, Bain & Company. At the end of the summer, Rigby came away with a full-time offer from Bain. He’s now a partner and head of Bain’s global innovation and agile practice.

Rigby has spent much of his tenure being an expert Explorer. His process is to constantly ask himself, “How can I make my job at Bain the perfect job?” Step 1: Explore an idea for disrupting the job. Step 2: Test the idea. Step 3: Sell senior executives on the change he has in mind. Bain welcomes innovation, but you need to make your case.

It helps to have leadership that lets you explore and test. For example, fifteen years ago, Rigby saw an opportunity to start an innovation consulting practice. He pitched the idea to Bain’s operating committee: “I said, ‘Let me try it for six months, and if it doesn’t work, I’m happy to find something else. But if it does work, then we’ve created a new platform that could be good for our clients and good for us.’ ” They gave him six months to test.

As the leader of Bain’s retail practice at the time, Rigby had the idea of helping retailers innovate in order to adapt to the meteoric rise of online sales. Working with some remarkable partners, Rob Markey and Jimmy Allen, who were willing to share their budget allocation and give visible support, Rigby was able to bootstrap the experiment, build credibility and ultimately establish the innovation practice at Bain. As Rigby explored better ways to innovate, he came across agile practices in the technology departments of many retailers.¹³ He says, “At first, agile scared me. I didn’t like all the jargon. And it was a language I wasn’t convinced I wanted to learn, but eventually decided I had to do it.” More exploration.

Smart growth leaders willingly try new things and jump to new S Curves of Learning, even when the leap is challenging. Rigby’s new S Curve was testing agile methodology. It has since become a core component of nearly every practice area in the Bain system.¹⁴ Forty years and counting, Rigby is still in his dream job.

Influential management thinker and professor at Columbia University Rita McGrath has found that the root cause of failure in new business ventures is viewing untested assumptions as facts. She explained to me that business leaders are susceptible to being caught up in a project emotionally, without taking a hard look at the probable costs and outcomes.¹⁵ “With their eyes on an attractive prize, leaders often underestimate the difficulty of getting there, substituting optimism for data.” They explore without testing. Especially with a high-stakes opportunity, it pays to devise a low-commitment test: minimal cost, a short time frame, and a relevant metric before fully committing to the course.

3. Is It Familiar Yet Novel?

Is the S Curve of Learning I’m exploring familiar enough to be navigable, yet novel enough to promote growth?

Explorers should look at S Curve opportunities in terms of both their familiarity and their novelty. You need some of both.

Familiarity helps you relax and feel safer; too much familiarity may mean stasis. The unfamiliar in small doses surprises and delights and can lead us in new directions. Darrell Rigby wasn’t familiar with agile methods, but he knew enough to see their relationship to other areas and take on the challenge. In large doses, novelty and uncertainty create anxiety and fear. For me, training for an Everest expedition or becoming a UFC fighter are currently too unfamiliar.

It’s important for Explorers to realize there will be some discomfort at the start of any worthy S Curve. Psychologists use the term “premature cognitive commitment” to identify the human and animal tendency to cling to familiar assumptions, even when new facts are brought to light. One recent study posits that of the 6,200 or so individual thoughts that we have per day, only a small percentage are new.¹⁶ Cognitively speaking, we rarely explore new routes.

To illustrate the dangers of this, consider that in India, an elephant calf is easily kept in place by being chained to a small stake in the ground. How do you keep a six-thousand-pound adult elephant from taking off? With the same small stake and chain. The elephant is held captive by its premature cognitive commitment: I didn’t escape this before. I can’t now. Similarly, we may think learning something new is an impossible hurdle, when in fact it’s just a token barrier that’s easily overcome.

In early 2020, I interviewed Tara Swart, a neuroscientist and former psychiatric doctor, now a senior lecturer at MIT Sloan School of Management, who told me:

The brain becomes less malleable. The child’s easy gift for picking up a language, a subject, or an instrument gives way to the adult’s old-dog-new-tricks mindset. From twenty-five to sixty-five, you really need to do things to push yourself through that S Curve.… It has to be something that’s sufficiently difficult that it makes you sweat mentally, as it were, to actually change your brain.¹⁷

Academic research suggests there’s an optimal ratio of tried-and-true to the new.¹⁸ Brian Uzzi and Benjamin F. Jones, professors at the Kellogg School of Management, analyzed 17.9 million research articles over ten years. They found that academic papers that combined about 85 to 95 percent familiar sources with 5 to 15 percent novel sources were twice as likely to be high-impact papers, as measured by citations. Their conclusion seems to concur with our general human tendency to want some new knowledge to build on the firm foundation of what we already know.

It’s the same in music: when Hit Makers author Derek Thompson studied why songs become popular, he found that “ninety percent of the time people listen to music, they are listening to a song they have already heard.”¹⁹ Storytelling follows the same pattern. The hero’s journey narrative is so cemented in our cultural consciousness that, from the Odyssey to The Lord of the Rings, we take it for granted and are shocked when a story deviates from it. That means that only 10 percent of the time we are listening to songs we haven’t heard before and watching movies that are truly original. Surprisingly little of what we consume is actually new.

Extrapolating from the research, do you have approximately 85 percent of the know-how you need to succeed on an S Curve you are exploring? Is at least 5 to 15 percent of what you are considering novel enough to stimulate your brain to change and grow?

Entrepreneur Jamie O’Banion was exploring her option to start a business in the cosmetics industry.²⁰ Much of her exploration told her this was familiar ground. Her father, Dr. Terry James, is a well-known dermatologist who owned a cosmetics lab while O’Banion was still in elementary school.

The science of skin care was dinnertime conversation in her childhood home. As a teenager, she accompanied her father on visits to European and Asian laboratories and manufacturing plants. Later, she was a part-time model and spent time working in marketing and product development at her father’s company, where she was exposed to cutting-edge science and scientists, makeup artists, creative directors, and brand professionals.

The industry was familiar. But O’Banion also wanted to start her own business. That was novel, a new frontier of unfamiliar leadership and management skills. She founded BeautyBio, and the mix of familiar and new paid off.

In her 2011 original product launch on Home Shopping Network, her inventory sold out in minutes. A 2016 rollout of a proprietary micro-needling tool netted $4 million in sales in twenty-four hours. Today, BeautyBio is a $100-million-plus business. This may sound like overnight success, but O’Banion’s exploration of this S Curve started in elementary school. Her launch point of slow growth lasted two decades. She has successfully coupled beauty product science and continuous innovation while learning essential business skills like putting together a profit-and-loss statement. She’s leveraged the familiar and embraced the unfamiliar to achieve impressive, smart personal growth; her business, not coincidentally, has grown smartly too.

Is the ground you will cover sufficiently novel?

4. Does It Fit My Identity?

Is this S Curve of Learning compatible with my identity? Is it compatible with how I see myself and how others see me?

An S Curve worth pursuing will dovetail with who we aspire to be. Exploring areas of ourselves and possibilities that have no apparent connection to who we are right now is exciting. It may even be admirable, but it may also mean we get voted off our current island. People around us, including those we care deeply about, may be heavily invested in who we are now: our family, friends, colleagues, and community. Religious devotion is a prime example. If a particular faith is central to your family’s culture or history, even glancing at a map of different belief routes could trigger social backlash.

It’s less difficult to take on a new learning curve if it aligns with our current identity. Here, again, balance is necessary. If the new S Curve we’re exploring is too aligned with who we already are, the potential for growth may be too low. But if it’s too far out of alignment, then the price of reaching for a new identity may be too high. I’m not suggesting we automatically pass over opportunities that are significantly divergent from our current identity. But we do need to explore the cost to our meaningful relationships and our sense of self before we make the leap.

Victor Wooten is a music man. This is his identity. He is a bassist, an original member of Béla Fleck and the Flecktones, and the winner of five Grammy awards. Long before he took the stage at Carnegie Hall, Wooten’s first gig was with an eclectic quintet, the aptly named Wooten Brothers Band (his bandmates were his four older brothers). Victor was six years old. “I was born into a band,” he says. An older brother started Victor on bass guitar when he was two. “Music is a language,” Wooten says. “It’s a lifestyle.”

Today, Wooten’s range of instruments includes bass, cello, upright bass, guitar, keyboard, drums, and percussion instruments. He became a music educator, then a producer, and then the owner of Vix Records, his own indie label. We could imagine Victor Wooten taking on virtually any learning curve in the world of music.

But is it part of Wooten’s identity to write a novel? It might be surprising to learn he has—until we meet Wooten’s protagonists, three musicians doing battle against an enemy who is trying to destroy all musical sound. Writing a novel was, well, novel, but the creative act and the subject he chose were in harmony with his identity.

However, we’d probably be surprised if we learned that Wooten was exploring computer programming. This doesn’t align with how he shows up in the world, to himself or to others. It doesn’t mean he couldn’t be a computer programmer if he wanted to give that a try. But he would need to be prepared for the emotional, psychological, and social cost that can be attached to such a significant identity shift. Concluding his popular 2019 TEDx talk, Wooten signs off with “My name is Victor Wooten. I’m a musician.” A declaration of a positive personal identity.

5. Is the Reward Worth the Cost?

Is what I will gain sufficient to offset the tangible and emotional costs of scaling this new S Curve?

Exploration includes a lot of calculating of cost and benefit. Karen S. Carter started out as an intern at the Dow Chemical Company when just a freshman at Howard University. Carter desperately wanted to finish college, but she knew that her widowed mother could not afford to pay for all four years. Even if it came with the stress of working and studying at the same time, graduation was a dream for which she was willing to pay the price.

She gradually ascended the corporate ladder, but not in a straight line. Early in her career, she was offered a position in human resources. It was neither what she was doing nor what she wanted to do. She declined. The vice president of HR quickly made it clear to her that they weren’t asking if she wanted the role—they were telling her it was her next role: either grow or go.

Carter wasn’t enthusiastic about exploring this opportunity, but Dow was too good to lose. And it was a caring push, not a shove. Carter was in an ecosystem where her potential was recognized. Dow had made a point of periodically offering her plum new roles and growing experiences. Plus, Dow was invested in her growth in the strict financial sense: it had paid for her MBA.

Her reluctant yes to the HR job was yes to a career she couldn’t have imagined: Carter is now Dow’s chief human resources officer and chief inclusion officer. She describes it as the ultimate stretch assignment. It’s challenging, and fulfilling, to oversee people operations at a firm with more than fifty thousand employees. Her creed is that of a smart growth leader: true growth and comfort cannot coexist. She says it’s not a question of if but rather when we get upended. Disruption is a pay-it-forward principle, so share the tough love: 1) get disrupted; 2) seize the growth opportunity; 3) share it with others. Carter grows herself, grows her people, grows Dow.

Sometimes S Curves aren’t totally voluntary. Circumstances, or other people who see potential in us, give us an unexpected push. Preplanned or unforeseen, thrilled or terrified, you’ll need to determine whether the reward of being on a specific curve is worth the cost. Even if the reward doesn’t initially seem greater than the cost, if you are like Carter, you will find a way to make the numbers add up.

6. Does It Align with My Values?

Is this S Curve of Learning aligned with my core values?

Explorers, ignore this question at your peril.

In 2007, I attended the last day of class for the course, “Building and Sustaining a Successful Enterprise,” taught by my mentor, the late Clayton Christensen. In his final minutes with eighty of the world’s best and brightest young business students, he could have used his bully pulpit to say many things. He focused on building and sustaining a happy life. He said, “In just a few months you will graduate from Harvard Business School, and embark on what to many, including yourselves, will be prestigious, lucrative, high-profile careers. But if you want to also have happy lives, you need to know the purpose of your life.”

That last day of class lecture eventually became a TEDx talk, and a book titled How Will You Measure Your Life? in which he shared,

While many of us might default to measuring our lives by summary statistics, such as number of people presided over, number of awards, or dollars accumulated in a bank, and so on, the only metrics that will truly matter to my life are the individuals whom I have been able to help, one by one, to become better people. When I have my interview with God, our conversation will focus on the individuals whose self-esteem I was able to strengthen, whose faith I was able to reinforce, and whose discomfort I was able to assuage—a doer of good, regardless of what assignment I had. These are the metrics that matter in measuring my life.²¹

The measurement of our life, in the final analysis, will fall short of what we hoped if the work we are doing, the time we are investing, and the things we are accomplishing don’t lead us in the direction of our deepest aspirations and our most deeply held values.

Nearly two centuries ago and just a few short miles from where Christensen lived and worked, Henry David Thoreau said of his time spent at Walden Pond, “I went to the woods because I wished to live deliberately … and not, when I came to die, discover that I had not lived … I did not wish to live what was not life, [for] living is so dear.”

S Curves that become an emotional, spiritual, or physical detriment to us may let us grow, but it won’t be smart growth. Not all growth is advantageous. Not all S Curves lead to where we want to go. The S Curves of Learning we explore and ultimately choose to pursue should be true to who we want to be.

That has been the case with Angela Blanchard. For over two decades, Blanchard served as president and CEO of Neighborhood Centers, Inc. (now BakerRipley), the biggest community development nonprofit in Houston, Texas, ranked in the top 1 percent of charitable organizations in the United States.

Much of Blanchard’s career has focused on lifting the “lowest-income people, which overwhelmingly included newly arrived immigrants and people of color.” She helped them find homes and jobs and obtain US citizenship. Blanchard believes the United States is lucky to receive these high-achieving new taxpayers and wanted to help smooth their transition.

“My focus over the last decade,” she told me, “has been on the experience of people displaced by ‘war or weather.’ ”²² Blanchard is a seasoned executive who has directed budgets approaching $300 million, but she prefers to describe her work with a single word, service. Her top value and her true identity are to be a helper in the world to those who have lost everything. Now a senior fellow of international and public affairs at Brown University, Blanchard told me she’s “obsessed” with bringing immigrants’ stories into the public consciousness. “It’s to remind us of our humanity,” she said, “because … all of us are essentially shipwrecked, trying to figure it out together.” Blanchard is living a smart growth life, in part because her expertise and her core values are totally aligned.

Blanchard’s case seems easy. She has such a clear sense of her identity and values that the exploration hardly seems difficult. But assessing if an opportunity is aligned with our values is usually easier said than done. We are complex creatures, and our hierarchy of values isn’t always straightforward. We have our stated, public-facing values. Mine, for example, are to grow in wisdom (apply knowledge judiciously) and stature (while increasing my height isn’t an option, I can accumulate resources to do good), and in favor with God (live according to the standards of a higher power) and humans (treat those around me with dignity).²³

But we also have hidden or “shadow” values that don’t meet the public eye. We live by both. Our stated values can express what we truly want, but often merely express what we think we ought to want. For example, we might publicly—even sincerely—express how much we value teamwork, but then conflict arises when our desire for personal credit, a promotion, or leadership status undermines our outward team spirit. Explorers must face the fact that wanting to want something is not the same as genuinely wanting it or giving it priority over other, unacknowledged values.

Exploration involves excavating our shadow values. Wanting personal credit, for example, because as a child if you weren’t the best, approval was withheld. This dynamic was the seedbed for a shadow value. Get along with your schoolmates, but make sure you win. Obscured values are often the default setting that govern our choices, but because they are less socially acceptable and productive than our stated values, we try to keep them hidden. Shadow values may live in the shadow of our consciousness, but they are in relief in our behavior.

Unearthing our shadow values and rooting out the cognitive dissonance caused by holding two conflicting values are essential in exploration. Shadow values emerge to protect us, but left unchecked they will choke our growth, and the growth of those around us. They are like cancer cells and weeds; both grow, but at the expense of healthy ecosystems. It’s understandable that we want our less socially acceptable values to stay in the shadows, and yet what we avoid or even run away from is almost always the richest raw material for meaningful growth.

Know what your shadow values are. Understand what aspects of your personality feed them, or perhaps what may have happened early in your life that made these shadow values powerful to you. Then bring them out of the shadows. This both honors the experiences that brought them into existence and loosens their grip.²⁴ New York Times columnist David Brooks expresses the paradoxes of value-oriented growth,

You have to give to receive. You have to surrender to something outside yourself to gain strength within yourself. You have to conquer your desire to get what you crave. Success leads to the greatest failure, which is pride. Failure leads to the greatest success, which is humility and learning. In order to fulfill yourself, you have to forget yourself. In order to find yourself, you have to lose yourself.²⁵

7. Is This My Why?

Do I understand my why in life and do I understand why I would undertake this new S Curve of Learning? Do these two whys intertwine?

In 1980, John Mackey cofounded Whole Foods Market. The future organic food giant began life as a small health food store, SaferWay, in Mackey’s hometown of Austin, Texas. By 2000, Whole Foods had grown into the undisputed leader in the healthier foods market, at the same time retail had begun its unstoppable march to the internet. Whole Foods had to keep step. The organization purchased a mail order vitamin business based in Boulder, Colorado, with the intent of making it “the foundation for our own e-commerce outreach,” Mackey says. He and his wife moved to Colorado to lay the groundwork for that initiative.

Returning to Austin a year later, Mackey was shocked to discover the senior executive left in charge during Mackey’s hiatus wanted him ousted, as did some of his board members. He was the only CEO the company had ever had. Now the board was meeting to decide whether his tenure was over. He recalls, “I was anxious about the meeting because I didn’t know what the outcome was going to be. But I got into the stores, and I don’t know how else to put it, except I had a spiritual experience. I realized that my higher purpose was to be doing Whole Foods. It wasn’t time for me to leave.”

That epiphany was a why moment, when Mackey realized that Whole Foods was more than a job: it was a purpose. Mackey survived the board meeting. He is still the company’s one and only CEO, now forty years on. But the near miss with getting fired changed his perspective. From that moment, Mackey’s goal became to be a more loving and conscious leader. A few years after surviving that scare, he announced in a companywide letter that he was cutting his annual salary to $1 and giving his stock portfolio to charity: “I have reached a place in my life at which I no longer want to work for money, but simply for the joy of the work itself and to better answer the call to service that I feel so clearly in my own heart.” Mackey later capped Whole Foods executive salaries, set up an emergency fund for employees in need, and started funding nonprofit organizations working to promote animal welfare, sustainable agriculture, and healthier food choices.

Being true to your why results in growth. You are conscious of your life’s purpose; you’re focusing your time and effort in areas that further your purpose. And when you grow yourself, you can grow your people. When Mackey focused on growing himself, his people grew, and so did his company. In 2000 the company’s stock traded at $5. In 2017 it was $42, and the retail juggernaut Amazon was preparing to buy Whole Foods for more than $13 billion. John Mackey is the textbook example of a why in action, even if he was forced to explore that why in a critical, stressful, and compressed moment.

When contemplating a new opportunity for growth, consider what motivates you—the why behind what you are doing. As twentieth-century American novelist, poet, essayist, and environmental activist Wendell Berry put it, “The world is full of places. Why is it that I am here?”

Exploring my why helped me recognize that I wouldn’t stay in the investing business forever. It was a challenging revelation. I was good at picking stocks. I could build a decent financial model. I liked being able to say I was an investor. It made me feel important. This was my identity.

But I didn’t find myself thinking about the market when I didn’t have to. I was far more excited by investing in people. For example, in 2002, while still an equity analyst, I read Tom Peters’s article, “The Brand Called You,” published five years earlier. American Idol was also beginning to peak in popularity. I decided to start one of our team training meetings by talking about how American Idol contestants each had a brand—the diva, the comeback kid, the oddball. I then asked every analyst to think about their own personal brand. Were they a stock picker, an industry expert, a connector? I loved preparing that presentation. I spent every spare minute thinking about these ideas and their implications for my colleagues. And I wasn’t being paid to do it—not really.

Five years later, I was investing alongside Clayton Christensen, subconsciously transitioning to what I do now. During a conversation with UN Foundation communications director Chrysula Winegar, she said, “You don’t just invest in stocks, you invest in people and their dreams.” Bingo. My why. This sounds punchy. But it goes to my deeper purpose; when I interact with you, I want to be invested in you—for you to have a greater sense of who you are and who you can be, not just professionally, but personally, as a human being.

If you don’t yet know your why, Simon Sinek provides a brilliant exercise.²⁶ Ask the people who know you well why they enjoy being around you, and what their relationship with you does for them. If you can get candid, straightforward answers from them, their answers will reveal to you your why.