“I never anticipated problems stemming from being female,” Greenlaw writes, “and never encountered any.”

  The reason: fishing isn’t a line of work defined by who or what.

  It’s a line of work defined by when.

  “There exist no nine-to-five swordfishermen,” she writes. “Twenty-hour days are the norm. . . . The game is never postponed due to darkness, and seldom delayed for weather.” There are no weekends, no holidays, no sick days. “When the lines are cast from the dock, all time cards are considered punched ‘in,’ not to be punched ‘out’ for over seven hundred hours—seven hundred hours of physical labor, in poor conditions, that you might not be paid for.” You might not be paid because when you leave shore, when you arrive at your destination, and when you cast your lines all determine how much you catch. No wonder, she writes, commercial fishing is widely considered “the most dangerous profession.”

  But as important as all those day-to-day whens are to that line of work—or to any line of work—each of us also faces a series of larger whens that shape our narratives about work—when we fall in love with a job, when we fall out of love, or when some perfect storm comes along and changes our lives forever.

  On October 28, 1991, Linda Greenlaw was captaining the Hannah Boden, the sister vessel of a seventy-foot swordfishing boat named the Andrea Gail. That night, off the coast of the Grand Banks, a nor’easter absorbed the remnants of Hurricane Grace, creating ninety-mile-per-hour winds and hundred-foot waves. The Andrea Gail and all six of its crewmembers were lost. A journeyman tree climber and floundering freelance journalist named Sebastian Junger had just “whacked the back of my leg” with a chainsaw and was limping around Gloucester, Massachusetts, when the storm hit. Three years later, he submitted a fifteen-thousand-word piece on the events of that night to Outside magazine, which ran a shortened version under the headline “The Storm.” That article became the 1997 bestseller The Perfect Storm, which in turn became the Hollywood blockbuster starring George Clooney and Mark Wahlberg.

  Greenlaw was in many ways the star of Junger’s book. She calls in Mayday for the Andrea Gail, and she reads the eulogy at the funeral; in the film she’s portrayed by Mary Elizabeth Mastrantonio. Junger calls Greenlaw “one of the best captains, period, on the entire East Coast.”

  The book changed Greenlaw’s life. First she was commissioned to write The Hungry Ocean; when it became a hit, she went on to write four more memoirs, four novels, and two cookbooks. In her forties she took in a troubled teen; in her fifties she got married for the first time; three separate times she retired from fishing, only to be called back. Today she runs lobster boats and leads moonlight tours.

  “To survive on the water is to course correct,” Greenlaw says. “You’re going from point A to point B, you have a destination in mind, but tides, currents, and winds can upset your course, and you have to adjust. You still get to your destination, but perhaps not in the same way you had originally intended.”

  And not in the same time frame, either.

  When is the forgotten element of most work stories.

  Herminia Ibarra, a professor of organizational behavior at INSEAD, says that even after a generation in which changing jobs became the norm, workers still overly rely on the linear plan-then-implement model of seeking work. This outdated approach, in which we keep replacing one job with the next, “presupposes an existing, fully formed self that gets exchanged for a new and improved model.” But our work selves are constantly changing, she says, in response to the world around us.

  I would go even further: Our work selves are constantly changing not just in response to our environments but also in response to a host of internal clocks. Our biological clocks. Our psychological clocks. Our guilt about being absent parents. Our sense that our bodies will soon give out. Altogether our work lives are being heckled every day by a chorus of inner voices that speak to us in messages we can barely make out, saying, Now is the right time; Now is the wrong time; How about next year?; Why not today?

  All of these clocks form the irregular ticktock of our work lives. They are the fickle timetables of When is your when? Sometimes they toll when you want. Sometimes they toll when you don’t want.

  Sometimes they toll all at once.

  Which is exactly what happened to Alexander Vindman one July afternoon in the Situation Room at the White House.

  Alex was born in Kyiv, Ukraine, when it was still part of the Soviet Union. He has a twin brother, Yevgeny, and an older brother. Their father, who is Jewish and a veteran of the Soviet Army, had a “plum job” with the city; their mother died of lymphoma when Alex and his twin brother were three. Alex’s father emigrated with the three boys to the United States, where he remarried and settled the blended family in Borough Park, Brooklyn.

  Alex was a science geek. He loved Star Trek and did well in school, but he didn’t work hard. “My brother and I were kind of the black sheep in that regard.” They followed in their father’s and brother’s footsteps and joined the military. “We heard all these stories about jumping out of planes and helicopters. It sounded like just the kind of activity we needed to get back on track. Also, we were immigrants and intuitively embraced the narrative of giving back.”

  Alex served in the ROTC, graduated from SUNY Binghamton, and was commissioned as a second lieutenant in the army. But at ranger school, he got injured and had to bow out of that elite corps. “It was a major setback. I really had to overcome the stigma.”

  Which he did. Alex served in an anti-armor platoon along the Korean DMZ and a Stryker brigade in Washington State; after passing ranger school on his second try, he led an infantry company in Iraq, where he was wounded by an improvised explosive device, earning a Purple Heart. At that point he became a foreign area officer and, with his wife, returned to Ukraine as an attaché. “There was something familiar about the country, but it wasn’t really home. I’m American.”

  Alex found his calling as a national security analyst, along with the intellectual rigor he never felt earlier in his life. He earned a master’s degree in Russian, Eastern European, and Central Asian studies at Harvard, served at the US embassy in Moscow, became a defense specialist for the chairman of the Joint Chiefs of Staff. Then he was assigned to the National Security Council in the White House. In that capacity, Alex coauthored the national military strategy toward Russia and was part of the US delegation at the inauguration of Ukraine’s president, Volodymyr Zelensky, like him a Jew from Kyiv.

  Did his work seem linear? I asked.

  “There’s a kind of templated career in the military, and I was always outside of that, so no, it never felt linear. It’s like any other job. Details matter, performance matters, but timing is what matters most of all. You can be a rock star, but if your timing isn’t right, then nothing happens. History makes heroes out of ordinary men.”

  And in the summer of 2019, history met Alexander Vindman.

  Alex had been working in the White House compound in the same office that Henry Kissinger once occupied. A few months after he arrived, a series of questionable events began unfolding in Ukraine involving the West Wing, the State Department, and the president’s closest advisers. The events culminated in a July 25 telephone call in which the American president asked his Ukrainian counterpart to investigate a domestic political rival.

  “I knew immediately that if this became public that the president would be impeached. As a matter of fact, I looked around while still taking my copious notes to see if anybody else in the Situation Room registered the import of what was going on.”

  Afterward, Alex hurried to his twin brother’s office, which was also in the White House. He closed the door and said, “Eugene, if what I am about to tell you ever becomes public, the president will be impeached.”

  Within days, the call did become public. The House of Representatives subpoenaed many of the personnel involved, including Alex. In his opening statement, he thanked his dad for bringing him to the United States. “I am grateful for my father’s brave act of hope forty years ago and for the privilege of being an American citizen and public servant, where I can live free of fear for my and my family’s safety. Dad, my sitting here today, in the US Capitol talking to our elected officials is proof that you made the right decision forty years ago to leave the Soviet Union and come here to the United States of America in search of a better life for our family.” Alex relayed a story in which his father begged him not to rock the boat and asked why he wasn’t afraid. Alex told him what he later told me was his motto.

  “Here, right matters.”

  The president was impeached by the House but acquitted by the Senate. Three months later, Alex was fired from the White House. Five months after that, following “a campaign of bullying, intimidation, and retaliation,” he was forced to retire from the army after twenty-one years of service. He joined a national security blog, enrolled in a PhD program at Johns Hopkins, and wrote a bestselling memoir. It was called Here, Right Matters.

  What did he learn from this experience?

  “The moment was much, much bigger than me. And in a way, I was willing to sacrifice everything that I had worked for for this moment. I was a student of history, and I looked at this moment through a historical lens. I’m still young, but I knew this would likely be my mark. I was in the right place at the right time to defend the national security of the United States. In this case, not against an external adversary, but against an internal adversary. I didn’t want to miss the moment.”

  We all have moments in our lives that are defined by this confluence of work, fate, and time.

  Of who, what, and when.

  To fully actualize those moments is to grapple with all three of those dimensions, including the one that most people appear to struggle with—timing. Is now the right time for me to make this move? Is now the wrong time to pursue my idea? Should I push? Should I pause? Should I stay? Should I jump?

  Here are three questions to ask when you find yourself in that moment of when.

  Past: When Does Your Work Story Start?

  On Monday, January 27, 1986, I boarded Korean Air Lines Flight 007 from New York City to Seoul. I remember the flight number because the same plane had been shot down by the Soviet Union three years earlier. I remember the date because just as I landed in my ultimate destination, Osaka, Japan, to begin a semester-abroad program, the space shuttle Challenger exploded.

  That evening a group of international students went out to dinner. I ordered soba noodles, which were served on top of a lacquer box. I carefully poured the au jus–style sauce over the noodles, which promptly leaked through the slats and dripped on everyone’s laps. I had no idea you were supposed to dip the noodles into the sauce, not the other way around. When we departed, I left my credit card at the table. The owner ran down the street after me. My visit was off to an inauspicious start.

  Four days later I moved in with my homestay family. The Nagatas lived in a modest home in a crowded Osaka suburb. Their family included a teenage daughter who spoke minimal English; a father who worked for a large industrial company; and a mother who is among the loveliest people I’ve ever met. Her name was Makiko, and she had a high-wattage smile, librarian glasses, and a giddy laugh. Like her husband, she didn’t speak a word of English.

  We sat down to a welcome feast that Makiko had prepared using a few inches of countertop, two gas burners, and a toaster oven. All that equipment, plus a small fridge and sink, fit behind a shower curtain. Even with those limitations, Makiko served ten dishes, including braised chicken, steamed vegetables, a sweet potato cake in the shape of Mount Fuji, and, her specialty, homemade, warm liver pie. In my family, I was known for eating anything—except liver.

  I ate the pie.

  Afterward, I went upstairs and lay down on my bed. It was short and the family had learned that I’m tall, so they had gone around to all the neighbors and collected microwave and TV boxes, which they covered with towels and appended to the end of the bed so my feet didn’t stick out. I barely slept.

  The next morning I learned my first lesson about life in Japan. Breakfast is leftovers from the night before. So on Sunday morning, I was served cold liver pie. That afternoon I took a pad of crinkly air mail paper and wrote my first letter home. You’re not going to believe what happened to me today. I haven’t stopped writing since.

  My work story had begun.

  When does your work story begin? When is the moment that the energy enters, the momentum builds, the meaning starts to assemble? Did it happen when you were a child? An adult? Are you still waiting for it to happen? Did it happen once a long time ago and you want it to happen again? Knowing when your story starts will help you tell a better story, because all good stories, on some level, involve a break in time. Just look at some of the most iconic first lines in history: They’re all about moments when time starts over.

  Orwell, Nineteen Eighty-Four: “It was a bright cold day in April, and the clocks were striking thirteen.”

  Plath, The Bell Jar: “It was a queer, sultry summer, the summer they electrocuted the Rosenbergs, and I didn’t know what I was doing in New York.”

  Márquez, One Hundred Years of Solitude: “Many years later, as he faced the firing squad, Colonel Aureliano Buendía was to remember that distant afternoon when his father took him to discover ice.”

  The book of Genesis: “In the beginning God created the heavens and the earth.”

  What all of these openings have in common is that they involve a rearranging, a reinvention, a recognition that something is beginning anew.

  A change in when.

  I asked everyone when their work story started. A minority said when they were young. Chely Wright knew when she was three that she wanted to be a country music star; Lauren Nichols knew at nine that she wanted to enter public safety; Courtland Savage knew at ten that he wanted to be an aviator. All three fulfilled their dreams.

  A majority said their story started in their adulting years, that long decade between late adolescence and early adulthood. Nishita Kothary decided to become a doctor during those years; Eric Vélez-Villar an FBI agent; Nate Venturelli a welder; Shellye Archambeau a corporate CEO.

  But as popular as young adulthood is for starting work stories, almost everybody restarts their work story these days at some later point, as Chris Donovan did with shoes, Michael Smalls did with baskets, Cherie Scott did with sauces, and Beverly Jenkins did with writing.

  Sara Sherr did the same with music. Sara grew up in Philadelphia in a nontraditional home. Her mother was an art teacher; her father quit advertising to play bass in a cover band. “My parents divorced when I was young, so in elementary school, I would hang out in bars until three in the morning with my dad.” Her father eventually went bankrupt and turned to deejaying. “He remade himself again, and I admired that. I just accepted that work involved lots of change.”

  Sara tried molding herself to traditional jobs. She sold clothes at the Gap; she took a job in accounting at Urban Outfitters. “I heard it was a cool place to work, but I couldn’t handle the morning hours.” So she quit and returned to her nontraditional roots. Her work story restarted at thirty-seven when she opened a karaoke company, which allowed her to hang out in bars until three in the morning five nights a week. Philadelphia magazine named her Best Karaoke DJ in Philly.

  Ashley Brundage also restarted her life in middle age. Ashley was raised in suburban comfort in Florida. “I knew I didn’t operate like normal boys in my neighborhood, because I chose to act like Jennifer Grey in Dirty Dancing, not Patrick Swayze.” Confused about her identity, Ashley focused single-mindedly on work. Ashley started behind the counter at Boston Market and got promoted three times in three years, rising from hourly worker to supervisor to managing her own store. In her fifth year Ashley was named general manager of the year for the entire company. “It was like tunnel vision to ignore what was happening.” Ashley also got married, had two children, and bought two homes.

  But after twelve years, the blinders no longer worked. “I reached a point where I couldn’t hide any longer. I started seeing transgender people in society and on TV—Candis Cayne was the first recurring transgender character on network television—and I was like, Whoa!” Ashley sank into depression, torpedoed her jobs, lost her homes, and went bankrupt. She also decided to transition to presenting as a woman. “I thought, If I’m going to start at the bottom again, I might as well be me.”

  Unlike Wynne Nowland, whose role as an insurance executive provided stability during her transition, Ashley had to rethink her work life from scratch. Despite having served as southeast regional director for Boston Market, Ashley was turned down for 101 entry-level jobs; two interviewers called the cops on her for being “a man in a dress.” “Finally I decided to take control. I was a bit abrasive, to be honest. I’d walk into an interview and say, Hi, my name is Ashley Brundage. You can call me Ms. Brundage or Ashley. And by the way, you see this big thing on my shoulder? It’s a chip. I’m going to be coming into your organization to prove myself. But if you give me a shot, I’ll be your entry into the $1.7 billion LGBTQ spending market.”

  Ashley was finally hired as a part-time teller at PNC Bank for nine dollars an hour. “In the restaurant business I started at four bucks an hour, so that was an improvement!” Within five years, she was a vice president of the entire $17 billion company and was inducted into the employee hall of fame. “The only way to succeed today is to expect the unexpected.”

  Which is exactly how Ashley restarted her work story when she was forty-one.

  When the unexpected happens to you, start by asking, Am I continuing a story that started long ago or starting a new story that begins right now?