The strong message in all these answers is that we don’t write our work stories on a clean slate. Our upbringings shape our choices much more than we often admit. The purpose of asking yourself both the upsides and downsides you learned from your parents is to summon your skeletons out of the closet and bring them into the light. Those skeletons are already weighing on you; you’ll make better decisions if you sit them at the table along with the rest of your whos and have an open and frank discussion.

  Present: Who Is Your Waymaker?

  The next part of identifying Who is your who? is to identify Who is your dominant who right now? It could be a parent, a lover, a spouse, a mentor, a newborn, a boss.

  Or it could be a figure who comes into your life at just the right moment and opens a door for you to pass through.

  A waymaker.

  Shardé Davis grew up in a single-parent household in San Diego after her parents divorced when she was four. Shardé’s mother, a kindergarten teacher, was her primary caretaker. “As a child, I was a young Black girl in a predominantly white, affluent community. I never had words to articulate who I was.”

  Shardé’s childhood hero was Rachel Green, the character on Friends played by Jennifer Aniston. Because Rachel was a buyer at Bloomingdale’s, Shardé set her sights on doing that, too. At the University of California, Santa Barbara, Shardé joined various organizations, took her academics seriously, and started to get noticed.

  “I had a meeting with my mentor, Dr. Michael Young, the vice-chancellor, in my second quarter. He asked me, ‘What do you want to be?’ I said, ‘I want to be a buyer at Bloomingdale’s.’ He laughed. ‘No, Shardé, that’s not what you’re going to do. You’re going to be an academic.’ Then I laughed. ‘No, Dr. Young, that’s not going to happen. I don’t even like to read or write.’ He said, ‘I see you being president of a university someday.’ ”

  The next year, the dean of social sciences recommended that Shardé apply for the McNair Scholars Program, a federal initiative to help college students from underrepresented backgrounds prepare for graduate studies. “During the interview, the committee asked me what I wanted to do. I told them, ‘I want to be a buyer at Bloomingdale’s.’ They laughed. ‘No, you’re going to be an academic.’ I was like, Where are you people coming up with this stuff?! I was going to turn them down.”

  Instead, Shardé went on to win the Steven H. Chaffee Award for Excellence in Research for her thesis exploring divorce in Black families. “That’s when I realized, My gosh, this work is amazing!” She stayed on at Santa Barbara to earn her master’s degree, focusing on what she calls “the strong Black women collective,” how female friendships form the backbone of Black communities. The teenager who had been inspired by Friends now made friends the inspiration of her academic specialty.

  For all her success, though, Shardé was one of only four minorities in a graduate program of forty people, which left her feeling isolated and insecure. “There were a whole bunch of white people studying whiteness, but nobody was studying Black womanhood, Black families, and Black cultures.”

  Then another who stepped in. Shardé’s adviser transferred to Iowa and suggested that Shardé follow her. Suddenly Shardé found herself in a community that encouraged her academic interests. She went on to earn her PhD, investigating speech patterns in Black female friend circles, and, at the unheard-of age of twenty-five, published an academic theory of how Black women, often negatively pressured to be strong, channel those frustrations to strengthen one another. When Shardé entered the job market, she was snatched up by the University of Connecticut and nominated for tenure.

  When I asked Shardé how she could have been so wrong about her destiny and all those strangers so right, she used an expression from the church. “When I tell my story, I say that Dr. Young spoke over me. He laid hands on me. He used what we call prophetic words. The same happened with the dean. In the church, we talk about God using people as instruments. All these experiences were divine timing; they were spirits pushing me so that my steps could align with God’s purpose.”

  And they weren’t the last.

  Not long after the Black Lives Matter protests erupted, Shardé was watching television and feeling frustrated. “I kept thinking, Racism exists in law enforcement, but it also exists in academia.” She was sitting on her couch one day when she had an idea. “Maybe if I use narrative, I can bring about change.” So she shared a personal story on social media and attached the hashtag #BlackInTheIvory.

  “That was a Saturday night. The next morning a friend called me at 6:00 a.m. ‘Shardé, get up! People are using your hashtag.’ The rest of the day, #BlackInTheIvory just blew up. It was on the top twenty hashtags in the United States by Sunday night. By Monday morning, I can honestly say that my life had changed forever.”

  Shardé, who once dreamed of being a buyer at Bloomingdale’s, found herself as the face of a movement to change the conversation about diversity in the ivory tower. While it’s too soon to tell whether she will eventually become the president of a university, it’s certainly not too soon to say that the vice-chancellor who made that prediction was prescient. The door that he opened in her mind became the barrier that she broke down.

  “I needed people,” Shardé explained. “I needed someone to show me what I couldn’t see. When he spoke over me, it was the first time someone saw the golden thread in me in a way that allowed me to see it for myself.”

  In his influential 1978 book, The Seasons of a Man’s Life, the Yale psychologist Daniel Levinson talks about transitional figures, people who come into our lives and help move us from one realm to another. The crucial function these figures play, he says, is “to support and facilitate the realization of the Dream.” Begun in the 1960s, Levinson’s study included forty men, all between thirty-five and forty-five, all living in the Northeast, all American born. Eighty-eight percent of his subjects were white.

  These demographics might help explain why Levinson said transitional figures are “almost exclusively male,” “often situated in a work setting,” and “usually older by half a generation.” The ideal transitional figure, he concluded, is like a “responsible, admirable older sibling.”

  My conversations robustly confirm that we all have transitional figures in our work lives.

  They equally robustly contradict every other aspect of Levinson’s conclusions.

  Our transitional figures are not exclusively male, they’re not only found in the workplace, and they’re not always older. Instead, in a mark of how much gender diversity there is in the workplace, how much our nonwork lives now influence our work decisions, and how much we’ve all come to accept that the young can teach the old, our influences come from all parts of our lives—from the Call of Duty chat room to the addiction support group—and from all ages, from babies who demand our attention to spouses who need us to bring in more money while they start a new company.

  At any moment, anyone you know can be the who that redirects your life.

  The key is what message they have to deliver and whether you’ll be open to hearing it.

  I began calling these figures waymakers after one of my subjects used that term. Cherie Scott emigrated from India to Canada when she was sixteen. Having been in a girl band in Mumbai, Cherie split for New York City as soon as she could to study theater. Carrying only one piece of luggage and $750 stuffed in her bra, Cherie entered her dorm room. “My roommate was this absolutely gorgeous, fake-tan girl named Trish whose father was a professional golfer from Palm Springs. She and her mother were unpacking an entire array of Bath & Body Works green apple lotions and candles.”

  Cherie heaved her suitcase onto the bed and opened it up. “And, oh my God, I smell all the spices from my mother’s kitchen. After I had gone to bed the night before, my mother had toasted all her masalas, put them in satchels, and slid them into the top of my suitcase. Trish and her mother said, ‘What’s that smell?’ I was so humiliated I wanted to die.”

  She threw everything in the trash.

  Twenty years later, after Broadway never came calling, after an endless slog singing on cruise ships and at amusement parks, after marrying her record producer, nursing him through cancer, moving to Maine, and working in event planning, and after becoming a mother herself, Cherie was devastated by the death of her mom. “I instantly thought back on that moment in my dorm room—and I cried. That was my mom’s way of saying, I don’t care what you do with your life, how big of a star you become, whose wife or mother you end up being, you will always be my daughter and I hope you never forget it.”

  Cherie went into the kitchen that night and began cooking her mother’s recipes. She had to buy new equipment, new ingredients, and, of course, new spices. It took her a year to perfect the taste. When she did, she decided to open a gourmet sauce company called From Mumbai to Maine. “I realized I needed to teach my children about their heritage. I needed to give myself new purpose. I needed to continue my mother’s story. She was my waymaker.”

  Like Cherie’s mother, some waymakers are inspirers. Chris Donovan, the telephone operator, was inspired to pursue shoe design by meeting his future husband, Steve, the tie-dye artist. Mary Scullion, a first-generation Irish immigrant, was a postulant in the Sisters of Mercy in Philadelphia when she heard the legendary social activist Dorothy Day give her final address. “She taught me that work can be transformational.” Mary went on to cofound Project HOME, a support group for people experiencing homelessness that earned her a place on Time magazine’s 100 Most Influential People in the World.

  Some waymakers are enablers. Caty Borum Chattoo was a comedy groupie and underling at a Los Angeles think tank when she talked her way into a meeting with All in the Family producer Norman Lear, who created a job for her as senior director at his foundation. “Norman is one of the great enablers of talent. He has a long history of spotting talent, putting people in positions of responsibility, then getting out of the way. I’m not even a famous person and he did that for me. We’d go to meetings at a big talent agency, a $15 million donor would ask a question, and Norman would say, ‘I think Caty should answer.’ I was silly and irreverent and kind of bold headed, but Norman helped me discover a whole new brightly colored version of myself.” Caty is now the executive director of the Center for Media & Social Impact at American University; she created the Yes, and . . . Laughter Lab, an incubator for comedy and social action; and when the University of California Press published her first book, A Comedian and an Activist Walk into a Bar, the foreword was written by Norman Lear.

  Shellye Archambeau was a junior in high school in her working-class suburb of Los Angeles when she had “that obligatory conversation with a guidance counselor about college.” The counselor asked what she liked to do. “That’s easy, I like being in clubs,” Shellye said. “I like leading them.” The counselor asked what she wanted to do after college. “I don’t care. I just want a job where I can keep the thermostat at seventy-two degrees, I can eat out at restaurants, and I can travel, because those are all things I can’t do right now.”

  “Well, in that case,” the counselor said, “I think you should go into business.”

  Shellye asked what you call someone who leads a business.

  “When the counselor said CEO, I decided right then and there that I wanted to be a CEO.” Shellye earned her undergraduate degree from the Wharton School at the University of Pennsylvania. When she learned that most CEOs start in sales, she took a sales job at IBM, followed that with executive positions at Blockbuster and Northpoint, and at forty-one, became the CEO of MetricStream, a governance and risk compliance firm based in San Jose with $350 million in annual revenue.

  Some waymakers are confronters. Colin Bedell was born on Long Island to parents who divorced when he was young. His mother, a nursing home aide, moved the children to North Carolina, where Colin struggled. “I was a closeted boy growing up in the South, asking questions no eleven-year-old should be asking: Why are some people happy and other people aren’t? Why do certain people get along and others don’t? Why don’t my parents get along?”

  Colin had passions—beauty, fashion, spirituality—but with no idea how to support himself, he enrolled at SUNY Stony Brook to study law. The first day of junior year, his older brother was driving him to campus. “He pulls the car over and says, ‘Listen, no one in the family is going to tell you this, so let me be the first: Cut this shit out. You definitely don’t need to go to law school; you need to go to the city. Do things that light you up. Put on your angel wings like the Victoria Secret fashion show you love so much.’ ”

  Colin dropped out, went to work at Sephora for a while, and enrolled at Parsons, where he became valedictorian. “I gave the speech in front of the queen, Diane von Furstenberg.” But after losing his job at a clothing warehouse, he started posting horoscopes on the internet under the brand name Queer Cosmos. On the day his unemployment ran out, Colin signed a book contract. Five years later, Colin was writing weekly horoscopes for Cosmopolitan, doing readings for clients around the world, and advising sleep brands and dating apps.

  We all have ghosts; we have demons. But we have angels, too, and we have waymakers. Figures who show up at critical junctures in our lives and speak to us, speak at us, and speak over us.

  Who is your waymaker right now? What are they trying to tell you?

  And are you willing to listen?

  Future: I Want to Be the Kind of Person Who ______________

  The final step in appraising Who is your who? is to pull together what you learned from the whos of your past, along with what you’re hearing from the whos in your present, and begin to formulate a direction for who you want to be in the future. A bedrock of narrative career construction is that only you can do this work. Only you can decide what messages you need to heed and what direction you’d like to move.

  In the case of Who is your who? I asked everyone to complete this sentence about what they learned about themselves during their biggest work transition.

  I want to be the kind of person who _____________.

  Some people learned to embrace risk. Julian Vasquez Heilig was on a linear trajectory from earning his PhD in education policy at Stanford to working at the US Department of Education in Washington, DC, to becoming an associate professor at the University of Texas, when he decided to veer off course and start a blog about hot-button school issues. “I grew up lower middle class; my mother always said, ‘Work hard but work smart.’ Beginning when I was eight, I always thought, What am I doing now that is going to make me successful in the future? The blog was the first thing I did that went against that spirit. I could have offended someone or said the wrong thing. But if you want to have impact, you can’t be fearful. I realized I was in a moment when I wanted to leave bravely.” In five years, Julian’s blog was read by a million people in two hundred countries, and after becoming a full professor at California State University, Sacramento, he was named dean of the College of Education at the University of Kentucky.

  Some learned to venture out on their own. Tye Caldwell was born in Lexa, Arkansas, near the Mississippi River. His father was a truck driver; his mother raised farm animals. “We couldn’t afford the barbershop, so one day I saw a pair of shears lying around and offered to cut my brother’s hair. I’m a good artist. I’ll do it!” Soon he was cutting his family’s hair, his teammates’ hair, his teachers’ hair.

  After high school, Tye moved to Dallas, earned a cosmetology degree, and began working in a salon. “I paid $125 a week to rent a chair. My first week I grossed $175.” Within a few years, he was grossing $1,800 and opening his own shop. When a visiting stylist offered to rent a chair from him, Tye developed a side job matching traveling stylists with empty salon chairs.

  “After a while, I thought, There must be a service out there that does this, like Uber or Airbnb.” When he found nothing, he decided to build it himself. A friend introduced him to a venture capitalist in Silicon Valley. “When I told her my idea, there was a click on the phone. I thought she hung up. ‘Sorry, I dropped the receiver. This is a billion-dollar idea.’ ” Seven years later, ShearShare was in 646 cities and 11 countries. Tye and his wife were featured in an ad for Google. They were profiled in The Wall Street Journal. The press nicknamed their company Hairbnb.

  “I realized I was in a time in my life when I should stand on the shoulders of my ancestors and build something that I could be proud of.”

  But some learned things about themselves they never knew. New York City native Wynne Nowland grew up in Queens, attended college in New Rochelle, and then moved to Long Island to sell insurance. Wynne stayed with the same firm, Bradley & Parker, for the next thirty-four years, the last five as CEO, building it to $120 million a year in premiums.

  But as stable as that work life was, Wynne had an unstable personal life, burning through three marriages. Until, at age fifty-six, Wynne went through a nonwork workquake. “I would say it began when I was eleven, feeling like I didn’t fit. I was in a boy’s body, but I wanted to be playing with the girls.” Wynne compartmentalized those feelings for decades, but as society became more accepting of such feelings—and Wynne grew more confident at work—taking action became more realistic.

  “I left the office on a Wednesday. I had a couple of surgeries on Thursday. I was back in the office two weeks later.” Having presented for decades as a man, Wynne now presented as a woman. “My privilege made my transition much easier. I could afford to go to the best surgeon. I retained a stylist in Manhattan. And of course I had great insurance!”

  Wynne also had the support of all eighty employees—all except a few, that is.