Most important take away

Pulitzer-winning reporter Jodi Kantor argues that successful, fulfilling careers are built on the combination of “craft” (a hard-won, distinctive skill) and “need” (an independent read on what society will actually require). In an AI-homogenized, bot-gated job market, young people must resist cynicism by developing durable skills, forging direct human connections past the algorithms, and taking calculated risks rather than chasing either pure money or the illusion of a safe, frictionless path.

Summary

Jodi Kantor, the New York Times investigative reporter who broke the Harvey Weinstein story with Megan Twohey, joins Kara Swisher to discuss her new book “How to Start,” which grew out of a 2025 Columbia commencement address given during the height of campus turmoil. The Columbia students told her they did not want to hear about Trump, Gaza, or the administration — they wanted to know how to start their life’s work in a chaotic economy. Kantor, who has covered employment for decades, felt compelled to answer, in part because she saw rising dread and cynicism about the workplace and has a 20-year-old daughter of her own.

Key themes

1. Craft + Need as the framework. Kantor’s central thesis is that the happiest and most successful people combine a craft (a specific, hard-earned skill — like surgery, comedy, running a great restaurant, or investigative journalism) with a need (an independent assessment of what society will actually require over your working life). Craft is protective — nobody can take it from you, even when jobs evaporate. Need is propulsion. Both push back against the AI-era psychological message that young people “aren’t needed.”

2. Beware trendy “golden ticket” studies. Kantor warns against chasing the hot discipline du jour — Japanese in the 80s, genetics, Mandarin, computer science — as a shortcut to success. The better move is independent observation of durable human needs (healthcare, addiction, climate, poverty). LinkedIn CEO Ryan Roslansky’s advice: use AI tools to chase bigger needs, not smaller, safer ones.

3. Craft over passion. “Follow your passion” is outdated. A better measuring stick: at 11:30 AM on a random Thursday, are you engaged in the task in front of you? Are you doing something of value that others can’t do? Craft requires practice and patience — it’s “like learning the piano.”

4. The hiring process is broken and homogenized. Bots screen resumes; applicants use AI to write them; 150 applications can yield zero human contact. AI’s homogenizing effect strips out the spark, charm, and specificity that used to differentiate candidates. The counter-move is personal connection — cold outreach, informational conversations, leveraging alumni networks — reaching past the technology. The book includes Kantor’s investigative-reporter playbook for cold-calling strangers.

5. Take calculated risks early. In a scary world, young people crave stability, but careers require risk. A non-linear resume at 22 is fine; work for a startup, disregard conventional wisdom, try something new. Kantor dropped out of law school to become a journalist — “all my best career decisions were about disregarding what other people thought.”

6. Work for the best people, not the best brand. Between a faceless corporation and a lesser-known boss with a track record of developing young people, choose the boss — even if the pay is lower.

7. First jobs should cause “collisions” with reality. Avoid quiet, low-stimulation first jobs (lonely art-gallery receptionist, isolated research assistant, even — controversially — the Rhodes library). Pick high-activity environments: political campaigns, restaurants, anything with chaos, new people, and real stakes.

8. Consult your demons. Some of the most impactful careers are built by turning personal pain into professional purpose — Kantor cites a young woman pursuing addiction-psychology research after losing her brother to overdose, and her own husband Ron Lieber becoming a personal-finance columnist after a money-troubled childhood.

9. Money vs. meaning is a false binary. Kantor distinguishes financial stability (necessary) from chasing untold wealth (often self-shortchanging). Her three-part ask of young graduates: financial stability-plus, meaningful work, and a contribution to others.

10. Higher education is failing on career formation. Most universities — even elite ones — are disconnected from helping students find their life’s work. Alumni networks are often inaccessible. Kantor would lock university presidents in a room until they fixed this. SUNY’s John King had the best answer to “what do you tell the hardworking kid who got 150 rejections?”: add a new craft.

11. Me Too’s lessons still apply to entry-level work. The Weinstein pattern — predators weaponizing young people’s aspirations — remains universal across industries and cultures. The reckoning continues even amid political backlash.

Actionable insights for recent grads

• Build a craft: pick a skill you can compound for a decade-plus, and practice more than the next person.
• Do your own needs assessment — don’t outsource your career bet to a trend.
• Reach past the bots: cold-email, cold-call, show up, leverage weak ties; personal connection is now a moat, not a nicety.
• Differentiate on the page: resist keyword-stuffing that makes you look like everyone else.
• Optimize first jobs for stimulation and proximity to great people — not prestige.
• Take one calibrated risk per stage: a startup, a move, a non-obvious boss.
• Turn a personal loss or frustration into a career-shaping motivation if you have one.
• Don’t confuse financial stability with unlimited-wealth chasing; aim for stability-plus + meaning + contribution.
• Don’t write off work as a source of happiness prematurely — but also don’t let it become your sole identity.

Chapter Summaries

Origin of the book: the Columbia commencement. Kantor was invited to give Columbia’s 2025 undergraduate address amid campus chaos. Students asked her to skip politics and answer one question: how do you start your life’s work now? The speech went viral; she couldn’t stop writing, and “How to Start” was born.

Craft + Need. The two-part framework for a good career. Craft is a specialized, hard-won skill with protective value in an unstable job market; Need is an independent read on what society will require, a counter to fashionable “golden ticket” fields.

Craft vs. passion. “Follow your passion” is obsolete optimism. Craft is honed hour by hour and measured by genuine engagement with your daily work, not by lifestyle signaling.

Skating to where the puck isn’t. Examples of need-driven careers: durable fields (medicine, cancer care); personal-demon-driven work (Xaria, the Columbia grad studying addiction after her brother’s overdose); and LinkedIn CEO Ryan Roslansky’s call to use AI to attack bigger problems — poverty, hunger, illiteracy, climate.

The broken hiring process. Bot-gated portals, AI interviews, 150 applications yielding zero human contact. AI homogenizes applicants by rewarding keyword-match over spark. The solution: personal connection, cold outreach, reaching past the technology — Kantor offers her investigative-journalism cold-contact playbook.

The AI-abundance fantasy. Kantor is skeptical of the “robots will do everything, enjoy UBI” narrative. Young people need durable, well-crafted plans, not utopian assumptions. She points to the recent moon mission’s astronauts as a positive counter-image to the “Severance” workplace dystopia dominating pop culture.

Calculated risk and loan-laden grads. With an average $40K in federal loans, stability is rational — but risk is still a non-negotiable ingredient. Try something unproven; work for a startup; disregard conventional wisdom when it doesn’t fit.

Expert question from Vivian Tu (Your Rich BFF): money vs. meaning. Kantor distinguishes financial stability (required) from chasing enormous wealth (often self-shortchanging). Her three asks of young grads: financial stability-plus, meaning, and contribution.

Universities are failing the career mission. Most schools — even elite ones — don’t meaningfully connect students to their life’s work or to accessible alumni networks. At a Dealbook panel, top university presidents struggled to answer what to tell a hardworking kid with 150 rejections. SUNY’s John King had the sharpest answer: add a new craft.

First jobs: go for chaos and collisions. The worst first jobs are quiet and isolating; the best are high-activity environments (campaigns, restaurants, newsrooms) with real stakes, constant new people, and opportunities to do whatever needs doing — including painting the office. Swisher relates her own Washington Post origin story of stapled rejection letters and cold-calling Larry Kramer.

Consulting your demons. Personal tragedy or frustration can be career jet fuel: Xaria’s addiction research, Ron Lieber’s personal-finance journalism, oncologists motivated by family cancer. Taking pain and turning it into craft gives work unusual depth and meaning.

Work, meaning, and identity. For those who say a job is just a job, Kantor’s book isn’t for them — and that’s fine. It’s written for people who want a fighting chance at meaningful work without giving up family or community.

Me Too and entry-level vulnerability. Even a decade after Weinstein, sexual misconduct continues to exploit young people’s aspirations at the moment they’re most invested and least powerful. The reckoning persists despite political backlash; Kantor doesn’t want young people to view work purely as a danger zone but acknowledges the structural risk remains universal.

Queen-of-the-world fix. If Kantor could change one thing, she’d lock college, university, and high-school leaders in a room (with good food and ventilation) until they figured out how to actually help students find their life’s work. Swisher offers the reverse: let young people work first and have older people go back to school.

Closing. Kantor’s send-off: “You’ll be okay. Most of you will be.” Count your blessings, take the risk, build the craft.