CHAPTER 9

All the Ways Your Diamond Sparkles

You never realize how much of your background is sewn into the lining of your clothes.

—Tom Wolfe

What do you do once you’ve been let in? Once you’ve shown how you can enrich, through first delighting others? The answer seems clear: you just enrich. You do the work. And yes, it’s true—to a point. But not only do you need to do the work, you also need to guide how others perceive your work and your worth.

guide /gīd/

to direct, to steer; to influence the course of action

We need to guide because the levers that enable success are often outside our control. And those who pull the levers are making judgments and decisions based on their perceptions of our competence and character.

We can’t demand that others pull the levers, but it’s within our power to direct how they pull the levers. We have the ability to guide the course rather than settle for the course of action that others decide for us.

That’s what this next part of the book is about: how you guide others’ perceptions of you and how you can enrich. You must guide that process; otherwise those preconceived notions that others will have about you—and they will exist, whether they are benign or malicious—will guide in your place. And in doing so, you can use the biases that others have against you in your favor.

Guiding, Following, and Knowing Yourself

Be yourself. This is a piece of advice that we’ve all heard, and most likely given to others. I’ve said it many times. A friend is about to interview for a job and they are nervous. What do I say to them? Be yourself. Someone is giving a big presentation? Just be yourself. About to ask someone out on a date? What do people say? Again, just be yourself.

This advice is great in principle, given the benefits we derive from delighting others authentically. But it doesn’t give very much explanation. Without understanding the nuance of “being yourself,” it can be very dangerous. It doesn’t work for everyone. It’s complicated.

When people say, “Be yourself,” we tend to think first about what we are good at. Sometimes it’s something that people can put a clear label on and communicate easily to others—“I’m good at tennis; I was invited to the junior Olympics, and am ranked sixteenth in women’s singles,” or “I play piano, and I played at Carnegie Hall at the age of ten.”

Other people, like me, have a harder time describing what we are good at. When I was younger, the best I could do was to say that I was good at school. I loved school, especially math; when I grew up, I wanted to be a math teacher. I took pride in memorizing my multiplication tables, I loved the elegant way that solutions to long-division problems fit into neat columns, and I loved the symmetry required to solve algebra problems. Math came naturally to me.

A large majority of you are probably shaking your heads vehemently, either silently horrified or silently mocking me and secretly hating me. But I didn’t have an advantage in many other things. I was small and timid; I was last in line for just about everything else. This was one of the only areas I had identified where I had a natural advantage. And even then, it was something that I recognized as an advantage only after I encountered it as a bias that people might hold against me.

My sophomore year in high school, I had Mr. Heine for algebra II and trigonometry. And then I had him again for precalculus my junior year. (I’m a product of public schools. Not a huge budget for teachers, you know? So I tended to have the same teachers for multiple years.)

In the beginning, I adored Mr. Heine—truly worshipped the man. Mr. Heine also loved math. He loved it so much that he would squeal in delight when he drew a perfect parabola on the board. I learned a ton from him—about math, as well as about having an edge. Or the lack thereof.

Mr. Heine had a “perfect test” bulletin board. It was prominently displayed at the front of the classroom, hugging the blackboard. If you got 100 percent on a test—it had to be a test, not a quiz or a homework assignment—Mr. Heine would write your name on a gold star and display it on the board for the entire year. Now, this wasn’t just any gold star—this was the mother of all gold stars. This was a ten-inch star that Mr. Heine would meticulously cover in thick, shiny, gold-colored paper, with perfect edges. And then he would carefully apply vinyl lettering, with your name and the date of your perfect test, precisely centered and aligned on the gold star. It was truly beautiful to behold. And what made these gold stars so desirable is that they were scarce. It would be a surprise if Mr. Heine handed out more than five or six in any given year.

Over the multiple years that I had Mr. Heine for math, guess how many gold stars I got. Zero.

Now, that probably would have stung regardless, but what made it particularly upsetting to the fourteen-year-old version of myself was that there was another girl in my class, Elizabeth, who got nine gold stars over the course of those two years. Not to take anything away from Elizabeth, because she was probably damn smart. But I do remember looking at her test papers on each of the occasions that she got a perfect 100 (the test papers were proudly displayed next to the gold stars)—and observing that our tests always looked nearly identical. On each of those occasions, when I may have gotten a 99, I’d notice that she’d have written something like 7x = 49; x = 49/7 = 7/1 = 7. I, on the other hand, might have written something like 7x = 49; x = 49/7 = 7. I’d get a point taken off for not showing my work and including 7/1.

When I tried to ask him questions about why I got points taken off, he would tell me that each time I questioned his grading, he would take another point off. I stopped asking. I also stopped asking questions in class. I noticed that when Elizabeth was struggling with a concept, we would spend days on that topic, and I would become agonizingly bored. When I would ask for clarification, he would tell me that he couldn’t stop the entire class to explain, and that I should ask a friend to help explain it to me outside class.

At the end of that year, to be allowed into honors calculus for our senior year (rather than basic calculus), we needed to have a teacher sign a form. I remember sleepless nights, worried that Mr. Heine wouldn’t sign my form, even though I had gotten close to 100 on nearly all my tests. When I finally asked him to sign my form, he looked at me and said, “I don’t think you’re ready for honors calculus.” He signed the form for many others in the class, students who I knew struggled with math.

After that, I decided I no longer wanted to be a math teacher. I decided I was no longer good at math.

Self-Awareness Encumbers Our Ability to Guide

Self-awareness is a sense of who we are, what we value, and what our inherent strengths are. When we say “self-awareness,” we mean knowledge of who we are internally. But gaining an edge requires knowledge of your inner self and how it interacts with the outer world. It’s both within you and contextual. That’s what I didn’t yet understand.

We need to own who we are and the context—what is within us and what is around us need to complement each other in order for us to be successful. I didn’t understand that self-knowledge and self-awareness only go so far if you ignore the truth of others’ perceptions and don’t take control to guide them.

As far back as 1890, the philosopher and psychologist William James spoke about self-awareness as a source of continuity that provided an individual with a sense of “connectedness” and “unbrokenness.” As researchers gained more clarity and confidence into the construct, self-awareness came to be defined as the capacity for introspection and recognition of our own values, passions, aspirations, and interactions with our environment.

These early definitions, however, emphasized the self, rather than the social self. And modern-day examinations of self-awareness seem to do the same. Self-awareness has become the latest buzzword, with everyone trying to become more self-aware—as the popularity of BuzzFeed quizzes can attest. (Which episode of Friends best matches your personality? Which Disney princess are you? What city are you? What color best describes your personality? I’ll admit to doing at least a couple of these.)

Science has its own version of these quizzes—for example, the widely used Myers-Briggs Type Indicator (MBTI). The MBTI attempts to inventory your traits and place you into one of sixteen personality “types,” capturing all your attitudes and preferences (Are you more introverted or extroverted? Do you function more through thinking or feeling? Sensing or intuiting?) into one parsimonious label.

I’m the first to admit that I find tests like the MBTI to be a fun way for me to categorize and be more aware of my own values, feelings, and motives, and provide a context to talk to others about theirs.* But tests like this are problematic* for all sorts of reasons. Many do not meet the basic criteria of psychometric scales. In fact, tests like the MBTI lack general external validity, are based on outdated psychoanalytic ideas, and dangerously oversimplify to the point where they are no longer scientifically and methodologically accurate. In addition to methodological concerns, we should be wary of all these tests because they create the illusion that our “selves” can stand independent from externalities.

We use tests like the MBTI and often take them as gospel. But this popular conception of self-awareness doesn’t really account for contextual and interpersonal differences. This is detrimental to truly gaining a sense of self-awareness because personality is a continuum rather than a series of binaries. While I might tend to be introverted, in actuality, I’m somewhere between introversion and extroversion depending on the context. We’re all somewhere in between depending on the context.

Assessments like the MBTI assume static personality traits, when in fact the most successful people perceive their personalities and skills as fluid and are able to represent themselves differently and adaptively.* And therefore it’s damaging for us to think of our “selves” as static and monolithic because we may be missing out on opportunities and occasions in which we might have an advantage. When we neglect to pay attention to how context affects our personality, we also limit our ability to find and cultivate our edge based on the situation at hand.

What we want is to balance who we are with the external environment in a way that is additive, rather than limiting, so that we can, as Judy Garland once said, “be a first-rate version of ourselves, instead of a second-rate version of somebody else.”

We’ve been focusing on other people’s perceptions of us and how that informs our view of ourselves. What happens when we experience an internal conflict? How do we accommodate what others tell us we should be, while simultaneously gaining clarity and precision in defining this sense of self and guiding external perceptions of that self?

Most of us begin with a strong sense of internal self-awareness—a sense of who we are, what we value, what our inherent strengths are—before it is shaped by what others tell us about who we are, what we value, and what our strengths should be. As a student, I was intuitively aware that I was good at math. I would just absorb mathematical concepts, and it was something that was fun for me. It made me feel light, relaxed, and carefree.

But our natural awareness is chipped away as we become attuned to the opinions of others. We live in a loud world, one where we are interconnected to others, whether we choose to be or not. What we are able to achieve and how far we are able to go is often in the hands of others—managers who determine promotions, investors who determine the financial resources we’ll have at our disposal, partner organizations who determine our place in the market, and yes, math teachers who determine our future career trajectories. It is inevitable that we will be affected by how other people view us, and how they perceive us when we are merely trying to “be ourselves.”

We might think one way to cope is to ignore the perceptions of others—to silence the things around us so that we can hear our own voice. I’m certainly an advocate of mindfulness and meditation and understand how this provides abundant benefits—but it cannot be the entire solution. The reality is that we do operate in a world of interdependency. It’s impossible to isolate yourself from others’ opinions and ideas. Those who seek to rely only on their own voice and their own silence quickly find that it is not sustainable.

But it is also not about allowing the interactions and perceptions of others to define who we are without our input, without individual agency, lest we allow others to dictate our own values, feelings, motives, and desires. We allow others to damage us, just like I allowed Mr. Heine to impact how I perceived myself.

Instead, we have the power to guide how we position ourselves to others and hence how others perceive us—but first we need to understand our “self”: the perceptions we have of ourselves, and how we internalize others’ perceptions. Only then can we take an active role in guiding and reconciling the voices, opinions, and perceptions of others vis-à-vis who we know ourselves to be.

The path forward—the path to creating an edge for oneself—is therefore about acknowledging and receiving the perceptions of others, while simultaneously empowering yourself not to embrace and adopt those views. You can accept the perceptions of others so that you can consciously address them and confront them—but without embracing and internalizing them. For as we’ll discuss later, the views of others are overwhelmingly not about you at all—they’re about their own insecurities, their own goals, and their attempts to reconcile their own sense of self-awareness.

Were my fourteen-year-old self privy to this, I would have recognized how Mr. Heine’s perception of my skills affected my own self-perception. And that might have shielded me.*

You’re Not Selling Out When You Reclaim an Awareness of Your Self

In Newark, New Jersey, Ashley Edwards knows how to talk the right talk. Her father grew up in the inner city of Newark, and a large proportion of her family still calls it home. To her, it’s also a hometown, the city where she spends most of her time. She cofounded a tech nonprofit called MindRight to empower Newark youth of color to heal from the type of trauma—such as emotionally abusive relationships, neglect, and physical violence—that she observed and encountered in her own childhood.

Ashley is in her element at MindRight, talking twists and goddess braids with students while also helping them deal with the aftermath of seeing classmates being shot dead or dealing with parents being incarcerated. It’s often tough, but as a black woman, Ashley feels like she belongs. It is her home.

And yet her home at one time was Palo Alto, California, one of the highest-earning towns in the United States, where she attended Stanford University for her MBA. Before that, New Haven, Connecticut, where she attended Yale University and majored in economics. But the amazing memories she holds of Stanford and Yale are also interspersed with poignant memories of the struggles she faced and the feeling that the advantages those prestigious universities promised to bestow were for others, not for her. She remembers classmates who were offered financial funding from professors to start ventures for “ideas that were based on nothing.” Those offers were never even an option she considered available to her as she sought funding for MindRight.

Getting people to take her and her nonprofit seriously was a struggle from the beginning. She launched MindRight while at Stanford and approached investors at philanthropic foundations who financed ventures just like hers. She thought it would be a perfect fit, and maybe it was—but she wasn’t.

At first, investors told her to “come back to us after you’ve won more fellowship awards” so that “you can show us that you’re a serious contender.” She told herself that investors just wanted to know she had the credibility to do it (and tried to stifle any other thoughts, even as all around her, nonblack peers and friends from Stanford and Yale were being lauded as credible, talented individuals coming from prestigious institutions). Despite her degrees, she felt like she needed to prove herself over and over again because of the color of her skin. It made her resent the privilege of her top-tier education, and it made her frustrated and angry.

When she began to win prestigious fellowships—the very fellowships that had been cited by those investors a few months prior—she was told that she needed to “do a pilot first, so that you can get more data and can demonstrate more credibility.” After three successful pilots in Camden, New Jersey; Washington, DC; and Newark, where she was able to demonstrate not only a viable business model but also that they were already earning revenue, the message shifted yet again. This time, it was simply that they were sorry that they could not invest.

She eventually bumped into these same investors at panel discussions at various conferences and events, where she would listen to them talk about their commitment to equality and funding people of color. She heard how they were lauded for their commitment to diversity and inclusion, and how they were considered game changers in a new, inclusive social entrepreneurship ecosystem.

Ashley remembers the day she reclaimed an awareness of her “self.” She was in a meeting with another potential funder when, completely unrelated to her organization, he began to talk about Burning Man, the annual event at Black Rock City, a temporary city erected in the deserts of northwest Nevada where people come together to celebrate the arts, self-expression, civic responsibility, and decommodification, among other things. She played along. When he started comparing Burning Man to other festivals such as Coachella and Cannes, she continued to play along. At one point, the conversation felt surreal to her; the contrast between this conversation and those she’d been having with her students just an hour prior was stark.

She realized that her students in inner-city Newark would have no idea what Burning Man was—and yet she could carry on a scintillating conversation with opinions about this festival, and about Coachella and Cannes. These were places, cultural references, and topics that were also a part of her makeup—things that she had a perspective on and an understanding of, because of her time in top-tier institutions. She could talk this talk as well.

Rather than fighting to prove and reclaim her status as a highly educated minority woman from an “atypical” home city, Ashley decided to start owning her background and perspective. Funders, she realized, were partially driven by a lack of understanding of what trauma in Newark looked like. They had preconceived beliefs about who she, as a black woman advocating for mental health in inner cities, was and should be. And she realized that it was “crazy that I had allowed people to make me feel like it was about me—and not about them.”

She started doing all her initial interactions with investors over the phone—where investors could not tell by the sound of her voice that she was a black woman, and where she could connect with them based on her education and apparent privilege.

She gave herself permission to embrace both identities, carrying her Yale backpack to meetings with investors and not letting herself entertain any feelings of selling out her Newark family—she had earned her Yale identity just like anyone else there had.

She found that this was the most difficult part for her—feeling like she was selling out. But it wasn’t selling out. It was giving herself permission to embrace all the varied and complicated pieces that made her, well, her. Once she allowed herself to reveal all the facets of her experiences, even vulnerably discussing her trials with depression and mental health with investors, it allowed her to guide investors to a different level of understanding of MindRight. She showed that she was the rare person who intimately understood both the community MindRight served and the objectives and motivations of the investors who funded it.

Ashley realized that by embracing who she was—all her identities, her multiple selves—she was able to cultivate an edge for herself, which allowed her to associate more effectively with others in both worlds and show how she could enrich. As Ashley describes, “It helped me flow in these worlds. In both worlds. I felt like I was flowing, rather than being halted.”

“Being yourself” requires embracing all the varied and complicated pieces of yourself. For Ashley, embracing all her identities collectively gave her an edge. But for others, that may not be feasible, and external demands may force you in directions otherwise. People have expectations for how you “should” be.

Self-awareness, in fact, is made up of two components: internal self-awareness and external self-awareness. And these are inextricably linked. As William James wrote, “A man has as many social selves as there are individuals who recognize him and carry an image of him in their mind.” We come to know ourselves by observing how we fit into the fabric of social relationships and what others expect of us.

There are many versions of ourselves. And there are many versions of who others expect us to be. But with true self-awareness, you can guide others and the perceptions of others nonetheless.

One for Me and One for Them: Guiding the Expectations of Others

In the early 2010s, Ashton Kutcher starred in a number of movies. One was the dramatic biopic Jobs, in which Kutcher played the visionary Apple founder Steve Jobs. Another was the outlandish romantic comedy Killers, in which he played a goofy assassin turned good guy.

Kutcher was strongly advised not to take the role of Steve Jobs, for fear that it would negatively impact his career—a successful career that he had built playing the down-to-earth romantic protagonist.

A few months after Jobs was released, I met Kutcher at a conference. An audience member asked a question about the impact that actors could have in the world, and his response surprised me.

I’ll admit that I never expected to quote Ashton Kutcher in my entire life, but what he said that day has continued to resonate with me, and it is something that I have repeated many times when people struggle with trying to “be yourself” in the midst of societal and external pressures, demands, and realities. What he said was this: “I do one for them, and one for me.”

What he meant by this is that it is important to balance and consider external demands of who others want you to be while also giving yourself the freedom to embrace the realities of your personal choices. He has to decide what movies to do. His agent puts pressure on him to do certain movies. For a long time, he was seen as someone best suited to romantic comedies, movies in which it was assumed that his charm would sell tickets and bring in large audiences.

But what he wanted to do was artistic movies, things that spoke to him personally—theater productions, artistic and indie films. Films like Jobs. But he also knew that in order to survive and be successful in Hollywood he needed to maintain his audience and his relevance, by doing those chick flicks.

So how did he describe what he does? “I do one for them, and one for me.” One film that gets him the audience and maintains his celebrity. And then one that really speaks to him personally.

Some might see this as selling out. But I see it as an artist smartly guiding expectations and finding a way to thrive within others’ expectations. We are complicated creatures, with multiple identities. There may be some identities that are more salient in some situations than in others, but they are still very uniquely ours. Kutcher is both a rom-com lead and a critically acclaimed actor in ambitious films. He gave himself permission to own all his strengths, including the ones that weren’t as personally fulfilling but still served a purpose. When we have that kind of self-awareness, that’s when we can guide others without compromising our own ambitions and desires.

And so how do we get a strong sense of our self (while not excluding the external factors that we must depend on)?

As we’ve seen from many of the experiences of others described in this chapter, when we tell people to “be yourself,” it is confusing. There are so many versions of others. There are so many versions of ourselves. So first, compare yourself with yourself, not with others.

Second, remember that life rhymes. Look out for what rhymes in your life—the situations that seem to repeat themselves, the similarities in both your successes and your obstacles.

Third, as you begin to pick up on these patterns, don’t go for absolutes; go for directionality. We tend to want to package, in a neat little parcel, the sum of who we are. But it’s enough to just identify what areas are your “right directions” and which are your “wrong directions.” It’s actually better that way.

Going for directionality, rather than absolutes, helps you manage the impressions of others and guide their perceptions. You can be more fluid and adaptive, and you don’t have to try to guess at what exactly they want you to be (because as we saw, they don’t really know). You can embrace and bundle multiple identities, like Ashley Edwards was able to, or disaggregate and separate multiple identities while still owning them all, as Ashton Kutcher described doing. It gives you permission to be all the glorious versions of yourself.

If you go for general directionality, you’ll be more likely to avoid striving for goals that don’t leverage your strengths and that make it harder for you to create unfair advantages. Too often, we pigeonhole ourselves into what we think our strengths are, rather than building on those strengths. Rather than saying, “I’m an athletic person, so I’m going to try lots of sports,” we force ourselves into one particular sport that we are going to excel at no matter what. What we sometimes fail to remember is that we are not one-dimensional beings. Self-awareness, in and of itself, is an elusive goal. We never really know ourselves; the best we can do is find general directionality.

And finally, going for directionality allows you to simply move toward something that feels right, while already finding ways to cultivate an edge. Just start going toward something—don’t worry about if you haven’t yet found the direction. When you go in that direction, do you feel light, free, and happy? Or do you feel fearful, constricted, and dark? Is it a situation or an interaction that makes you feel this way? Rule out some of those, and your choices become clearer. Sometimes the easiest way to figure out your right direction is to know which ones are the wrong directions. And keep yourself moving in the right direction without limiting yourself.

Often, having a vague direction in mind leads to multiple opportunities for success rather than one chance to avoid failure. Your success is rarely dictated by one single outcome that constitutes the W on the win column. There are lots of different ways to win. That’s what we forget. We see one path that worked for someone else, and then try to replicate that, forgetting that there are infinite ways to get from point A to point B. And there are lots of point B’s.

For Kutcher, it was giving himself permission to embrace what would delight and enrich others, as well as what would delight and enrich himself.

For Ashley, it was about her ability to feel like she belonged when she was with students and community partners in inner-city Newark, but also simultaneously giving herself permission to embrace how she belonged and could be a part of the Yale and Stanford elite.

As for me, eventually I did find my way back to math. Even though I decided that I no longer wanted to be a high school math teacher, I never stopped loving math.

The next year, I had an amazing chemistry teacher named Mr. Kost, who encouraged me to go to college, and to major in engineering. I did, and I did.

But even as I studied to be an engineer, I recognized that I was a different type of engineer than other people, and was taught to recognize how I would have to guide.

Part of the difference was my gender. I remember electrical engineering professors talking about current by stating that many of us must have tried to stick our fingers into electrical outlets as kids, and remarking to myself that it was probably something boys usually did because girls were dissuaded from doing so, like I had been.

Part of it was my lack of experience and my lack of familiarity with and access to computers. I also remember a professor talking about processors and assuming that everyone had tried to take apart a computer at some point—and thinking about how I had never had a computer of my own, let alone taken one apart. In those days, computers were only something rich kids had at home—the only ones I had seen were the ones I got to use once a week in computer lab.

Given all this, it probably shouldn’t have been surprising that I found engineering to be extremely hard. Damn hard. So hard that I failed my first test in my very first engineering class, a computer science class, with a score of 37. Out of 100.

I quickly realized that I was probably going to lose my scholarship, but then two things happened.

First, I called my dad and told him that I wasn’t smart enough, and that I needed to switch majors. But he gave me a piece of advice that I still give my own students. He gave me permission to switch—as soon as I could tell him what major I would switch to and why I would like it better.

I couldn’t conjure up another major. He helped me realize that too often we derail ourselves from a path before we’ve even had time to refine it. When things are going badly, lots of different options look better. But if we think about it and try to visualize what even one of those other options might look like in reality, we realize they might be very much the same, or even inferior.

Second, my computer science professor, a wonderful woman named Dr. Laura Bottomley, called me into her office the next day after class. I thought she was going to tell me that I was going to fail the class and that I should drop engineering. But when I got there, she had a copy of my exam in her hands and asked me to explain my solution—in words, not in code—and to explain my thinking. And I did. She did the same for the next question and then the next. And then she paused and said, “You know exactly what you’re doing—you just don’t know the right syntax.” She gave me a C.

She asked me if I had ever done any programming before, if I had ever seen any programs. I told her that I’d taken a typing class in high school. She asked if I had a computer. I said no. She asked me about open lab hours at the computer cluster. By then I was choking back tears as I explained that open lab hours were at the same time as my work-study job.

She nodded, and then told me something that I’ve never forgotten: that she too had nearly failed her first engineering class, but that there is no right way or wrong way to do this; there is no one-size-fits-all. That I was headed in the right direction, and I should give myself the chance to go in that direction while embracing who I am and how I think about the world.

She told me that I may not have had the opportunities that others have had, and may never have those opportunities—but that I did have something. And that we are all diamonds; we are all diamonds that sparkle in different ways.

Self-awareness is like a diamond, sparkling differently from every angle. There are many facets of a diamond, and sometimes the light will hit at one particular angle, and other times it will hit at another angle—and sometimes it will hit multiple facets at once and appear spectacularly brilliant.

Cultivating your edge is about knowing each of your own facets and knowing how they will shine to those who are looking. There is no right or wrong way. Too often, even when people have a strong sense of self, they don’t use it. The advice to “be yourself” actually limits us from doing exactly that. There isn’t one singular version of oneself. There may be flaws and you may have disadvantages, but you have a diamond. And you can guide how your diamond is perceived, you can delight and differentiate, and you have the power to enrich.