My Career Crisis Party at Harvard

Nothing will deviate from the plan!

On Saturday, my friend Caleb and I threw a Career Crisis Pizza Party in our dorm at Harvard.

Here was the publicity email we sent out the week before, under the subject “CRY ABOUT YOUR CAREER (WITH PIZZA)”:

We had a grand scheme: get curious Harvard people to come to our career crisis party by tantalizing them with high-quality pizza, have them reflect on questions we wrote about work, money, and life, and then hand out copies of Paul Millerd’s book to people who we thought would benefit from it. People get inspired and leave the default path.

Here’s how we envisioned the conversations would go: “This party started because last year, Caleb and I went through career crises. Along the way, rather than apply for more jobs, we met people with completely different conceptions of life and work, such as Paul Millerd. He sent us thirty copies of his book The Pathless Path, which details his own experiences questioning his relationship to work. We thought this was an interesting conversation to start at Harvard. DO YOU WANT A FREE COPY, AND WILL YOU COMMIT TO READING THIS BOOK?”

Two days before the party started, we met a business reporter for public radio with a focus on people’s evolving relationships to work. She found the idea of a career crisis party — at Harvard of all places! — funny and delightful and asked to report on it. A real, established reporter writing an entire piece about us? We had made it, and this party was going to rock.

Foolproof plan, right?

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Saturday, 5:30 PM. A few people trickle in. We hand out our questions and encourage them to ask each other the questions. “Thanks,” they say as they stuff pizza onto their plates. Then they leave a few minutes after they come.

More people enter. I talk to someone who is very certain he wants to be a lawyer and wants to help with immigration. He wants to go into pro-bono law, but he thinks he’ll have to go into corporate law to pay off his tuition. Hopefully I can be a pro-bono lawyer at a corporate law firm, he says a little tentatively.

I have many doubts but don’t voice them.

I talk to another person at the party, and then another. I talk to people going into finance, consulting, and other standard paths. Many of them talk with a sense of resignation about their decisions. There’s a sense that out of the options available to them, they’re choosing the least worst option.

I want to ask how they could be so certain of themselves and the future, but I don’t. Don’t they know life might bring about curveballs? Don’t they know that they might change careers in a few years, that life has increasingly become non-linear?

“What’s your relationship to work like?” someone reads off of our questions to her friend.

“Toxic,” he replies. Then they start laughing.

I offer someone a copy of The Pathless Path. He accepts it but then leaves it in the room when he leaves.

Caleb offers someone a copy of the book. “Thanks, but I don’t have time to read,” one person says.

I talk to one of the grad students in my dorm and asked her why she took a pay cut to go to grad school. She realized she had enough money, even as she was going to grad school, so she didn’t need to salary max. I asked her about how she felt about owning a house, and she said she doesn’t really care.

How can you not want a house? I find myself wondering. Isn’t it a bad financial decision to be renting forever?

Caleb and I talk to another person who I’ve talked to a few times over the years. He’s going into finance. We ask him what number he’d feel financially secure with. He says the number he’d feel secure with is $50 million. I try to hide my shock. Caleb asks him what he’ll use the money on. My parents and my children, he says. Finance is the only way I can make enough money.

I want to scoff at the $50 million number. How can you need that much money? But then I think about my own number that I claim will make me feel secure, and realize I have the same problem, albeit at a much smaller scale.

Like him, I too am choosing to go into finance right out of college. For me, it’s because I have no idea what I’m doing, and trying trading seems like the least worst option (and has the biggest potential to be genuinely fun.) But the firm I’m joining works their new hires hard, and I’ll be in the office for 12-14 hours a day.

I’m trading (haha I’m good at puns) my time for money, in part because trading seems fun, but most definitely in part because I feel insecure — financially, professionally, status-wise, and otherwise.

Right now, I have dreams of leaving the default path of status and money and working abroad remotely, but I also have dreams of being one of those ambitious career women who are intense and good at boundaries and ridiculously successful. I keep telling myself that I don’t need a lot of money (I really don’t), that in my heart I’m just a girl from Michigan who wants to return to the Midwest and be chill forever, but at every moment when I’m offered a chance to be chill, I always turn it down.

My desire for intensity is as genuine as my desire for ease. Trying to burn either desire out of myself only results in pain. I can’t scoff at the part of myself who would choose to work in finance for years and climb up the corporate ladder, because she is as real as the part of me who wants to drop everything and move to Minnesota.

I’m not sure what I’m doing, and I’m not going to pretend otherwise.

Roasted by Paul!

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In another life, here’s how this career crisis party would’ve gone: Caleb and I distribute all thirty copies of Paul Millerd’s book, we all realize that our it’s time to prototype the futures we actually want to live, and everyone leaves the default path.

But that’s not how the party went, and that’s also not how my future went after I read The Pathless Path. Life didn’t change all at once from reading a book, at least not for me in this case. Instead the book planted a small seed in my mind about a different way to live. And, across time, as I keep watering that seed with the people around me — asking reflective questions, meeting new people who love their life, finding out what makes me come alive — I hope that the life I genuinely want for myself slowly starts taking shape.

The Gen Z crowd at the party might not read books for fun, but they did engage with the questions that we wrote. Under this framing, Caleb and I did plant a seed, and it’s too early to tell if something will happen.

Anyways, I’m not sure how to end this post, so here are some lessons I’ve learned or re-learned from the party:

• It’s hard to discuss a career crisis with undergrads who haven’t started a career yet.

• Gen Z will do anything for pizza, except read books.

• I have no idea what I’m doing with my life, but experiments are always worth running.

• There’s immense serendipity in putting your true self out there — maybe you’ll learn people’s stories, maybe you’ll make new friends, maybe a reporter will find what you do genuinely interesting. You can’t expect serendipity to come your way, but it’s always a gift when it does.