And Now for My Second Act

Finding a new career is hard. So I asked Stanford to do it for me.

March 2024

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Illustration of many Joel Steins trying new things.

Illustration: David Plunkert. Stanford Photos: Linda A. Cicero/Stanford News Service (7); mtreasure/Getty Images; Andrew Brodhead (2). Joel Stein Photos: Jackson Augustus Adair

I am 52 years old, have more than I ever wanted, and there’s an emptiness inside of me. The emptiness is not sports car–shaped. The emptiness does not feel like a “crisis.” The emptiness feels like the space between gears revving in neutral. It is a background frustration that bursts out in episodes of cranky old bastardom. It’s a dull form of the pain I endured for two years after I graduated from Stanford, when I couldn’t find a foothold in a writing career. Now, 30 years later, I am close to the summit of Maslow’s hierarchy and I want to jump off. 

When I heard about the Stanford Distinguished Careers Institute, it sounded like the solution to my simmering stew of ennui and anomie. DCI is a yearlong, nondegree program for people who feel finished with their first career and want to figure out what to do with the rest of their lives. The 41 people in this year’s program take a full load of both undergraduate and graduate courses in which there are available spaces. The average age is 60. I have always been precocious. 

Portrait of Joel SteinPhoto: Jackson Augustus Adair

There were, unfortunately, some reasons I couldn’t apply. First, I did not have a distinguished career. Since my time at the Stanford Daily, I have made my living writing self-obsessed articles full of penis jokes for magazines, a line of work that has become less meaningful for me and even less meaningful for society. After 20 years of writing a column and cover stories for Time, I am now writing an article for an alumni magazine that once ran a six-page profile about me. Second, I have a 14-year-old son in Los Angeles who is not interested in switching high schools for a year. Third, the cost is $72,000 (plus $40,000 for a spouse . . . plus housing in Silicon Valley), and I have made my living writing articles for magazines.

So I used this article as an excuse to try DCI out for a week. First off, I meet the director of the program, Katie Connor, ’79, MS ’80, who did the program herself in 2018–19. She used to run career development for the University of Colorado Boulder, where she told undergrads, “You’re lucky you have a career office. There’s no retirement office.” Now Katie runs a retirement office. 

While she is smiley and encouraging, Katie does not think I can resolve my career issues in a week. Or after an entire DCI program. “It’s unrealistic to think that you’ll leave after one year and have the epiphany. Think about college. That was four years. And you still had to go out and try different things.” That sounded reasonable, until I realize that Katie went to DCI and then took it over. It sounded less like she tried different things than that she tried no things. I want to be like Katie.

Although many DCIers arrive with a general area they want to pursue, 89 percent change their primary interest by the time they leave. And finding a new interest was going to be harder for me than most. Because the top field DCIers conclude they want to pursue, after “aging” and “spirituality,” is “journalism.” No one has left the program and gone into international tax law. That’s because as our time horizons shrink, our feeling of meaning comes less from impressing the world than from contributing to it.

Unlike similar programs at Yale (which focuses on character) and Harvard (which focuses on global impact), DCI is built around wellness, community, and purpose. It’s a journey to find yourself. Which is a phrase I made fun of when friends said it after graduation, arguing that I was way more interested in finding other people. At 21, I had already had plenty of me. So I went straight to imposing whatever I was on other people by writing in the first person. This, a DCI instructor argues, was setting a bomb. “You had a really good run. You didn’t know why you wanted what you wanted, and you got it. The question of ‘Why am I doing that?’ didn’t come up,” says Dave Evans, ’75, MS ’76, who teaches a version of his Designing Your Life course solely for DCI students. “Now you’re like a meerkat popping your head up out of the hole.” 

I learn that while my need for attention has shrunk, my desire for new experiences has not.

This was insightful, but I was more hoping Dave would tell me to get a PhD in philosophy or work for the State Department. I was joining a long line of frustrated DCIers in search of simple answers. “I thought it was going to be a job fair,” says Melissa Hollatz, ’94, JD ’97. “And I got here and they said, ‘First, we’re going to do all this work on you.’ It was kind of frustrating. I just wanted someone to tell me what to do.”

In Dave’s class, we huddled in groups to do exercises such as drawing maps of all the words related to one of our interests. Or writing down what we think the purpose of work is. I learn that while my need for attention has shrunk, my desire for new experiences has not. Dave argues that there are many good future versions of ourselves, which we should sketch out. Then we should immediately pick one and iterate toward it. He calls this a “bias toward action”—trying new things without long-term expectations, meeting people for coffee to find out about their jobs. I have, admittedly, been unbiased toward action for seven years, waiting for a path to materialize. Dave suggests imagining what we’d do if our current line of work suddenly disappeared from the planet. This is not a challenging thought experiment for me.

If there are at least three good versions of Future Me, as Dave claims, then there are at least three good versions of Past Me. And Melissa Hollatz feels like one of them. She was a year behind me at Stanford, went to Stanford Law School as I thought I would do, and worked her entire career at Palo Alto’s Wilson Sonsini Goodrich & Rosati until one day last year when, to her surprise, she answered the managing partner’s question of “How are you doing?” by quitting. I ask Melissa if she’ll let me be her DCI sidekick, and she enthusiastically agrees. This version of Past Me is much nicer than Actual Me.  

Melissa has a meeting with her group from her podcast storytelling course, which she took even though she’d never considered making such a thing. “Suddenly the stuff that wasn’t interesting to me—it seems like I want to do it. And there are people who want to help me with it,” she says. The two undergrads who signed up to make her podcast about DCI felt like they learned how to be more professional from her. And she’s been vampiring their energy, making her more interested in the project than anything she’s done in a while. 

Part of what makes DCI work is the same reason Stanford worked on me 30 years ago. Which is the same reason it worked on so many Silicon Valley entrepreneurs. Stanford is an optimism machine, a confidence generator where people embrace your ideas no matter how insane they are. In our senior year, when my friend Pete Huyck, ’93, had his ass shaved in White Plaza, hundreds of people came to watch as the Stanford Band played and people handed out sandwiches. Also, Google was created here. 

Melissa has a sardonic attitude, but since she’s been back on campus she has found a new earnestness. Everything feels possible. Some DCIers learn a language. “People think, ‘If I were to start learning about something this late in life, I’d be too far behind.’ We give that idea a swift kick,” says Becca Taylor, DCI’s assistant director. Max Bosel, a quiet, thoughtful 57-year-old who used to be the Mountain View police chief, says that within a few weeks at DCI, he realized he was going to revamp his idea of teaching first responders a financial wellness class. Because the idea wasn’t big enough. “I’ve been Stanfordized,” he says.

This, even more than a career, is what I want: enthusiasm. “I want to be used up when I die,” says Sonja Schoenwald, ’81, an energetic former mental health research scientist who, like nearly all her cohorts, carries a black DCI backpack everywhere she goes. “You need the juice. Don’t dry up.” I, too, want to rage against the dying of the light at a Kappa Sig party. Or, more realistically, hear about the party at our podcast meeting when the undergrads tell me about it.

‘You know what you like and what you don’t like. If you’re well resourced, how cool is that?’ he asks. For a second, I can see that it really is.

Melissa takes me to Professor Alexander Nemerov’s 11:30 a.m. course How to Look at Art and Why: An Introduction to the History of Western Painting. The lecture hall is nearly 10 percent DCIers, and as I stare at a slide of a painting by Diego Velázquez, I get why they are drawn here. Nemerov is an existential poet who barely talks about art, stalking the stage and expounding on our rare opportunity to explore ideas at a university. “We’re in this moment before we become middlemen. And we just quaff it down,” he says. Then, he expresses the thought in my head, the one about what to do with those ideas when I go back next week to being a middleman. “How will you put that into use? You will. Just don’t try,” he says. It’s so much more comforting than Dave Evans. But it’s not the Answer. Because I’ve been not trying for seven years, and it hasn’t worked.

On Wednesday nights, the DCIers attend their one mandatory class. Each session begins with a discussion with a Stanford professor, and then two DCIers deliver their Life Transformation Reflections, a 20-minute speech about an experience that changed their lives. Like most DCIers, Melissa cried when giving hers, which was about her father’s death. It bonds the group together and leads to deeper discussions. “Either this program is amazing, or it’s a cult. I don’t know,” Melissa says.

Tonight’s talk, “International Taxation: How Companies and Countries Compete on Taxes,” is by Business School professor Rebecca Lester. I do not see how learning about international tax law is going to help my life transformation. About five minutes into Lester’s presentation, I find that . . . I’m interested in international tax law. International corporate tax rates could be standardized to decrease wealth inequality! To raise funds for services! For a few minutes, I’m certain I should write a long article on international tax law.

After the LTR, nearly all the DCIers head to get burgers at Gott’s in Town & Country Village. In addition to riding bikes and wearing backpacks, DCIers revert to horrible undergraduate eating habits. These former CEOs, law partners, and doctors who can spend $72,000 a year on classes are eating an awful lot of pizza, takeout Chinese food, and burgers. I believe this is a huge part of why they love the program.

In addition to a customized spirituality discussion group, most of the participants sign up for John Evans’s DCI-only memoir class. I take a chair around the table and watch Melissa read her essay out loud to the group. They are more supportive than any writing class I’ve ever seen, impressed by her clever prose and willingness to share her frustration with always being a peacemaker. John, who has a tattoo on his left forearm that says “Love,” is a gentle, encouraging adviser. When I talk to him outside of class, he tells me he uses writing to help people remember who they were before they started their career. This allows them to re-create their self after they lose their identity as, say, a print journalist dad with a kid at home. 

What I have isn’t a problem, John says, but an opportunity. One that few people in the world have ever had. “You know what you like and what you don’t like. If you’re well resourced, how cool is that?” he asks. For a second, I can see that it really is.

I work on a memoir class assignment asking me to remember when I first became aware of mortality. It makes me realize what a conservative, nervous nerd I’ve always been, and how I require so much motivation to take risks. The kind of motivation, I’m guessing, that could be provided by spending a year with 41 fellow DCIers and 7,841 undergrads who think every idea is new. 

But even one week at DCI was enough to put my revving engine into first gear. In a bias toward action, I started a Substack called The End of My Career to iterate toward some book ideas. I have a meeting with a guy who wants help generating funny memes for his AI company. I sent an email to some journalism school deans about what it’s like to teach. And, every so often, I go online and look for opportunities to work on international corporate tax law.

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Joel Stein, ’93, MA ’94, is a writer in Los Angeles. Email him at

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