Jodi Kantor, Pulitzer Prize–winning journalist and author of How to Start, shares her winding path from law school to investigative reporting. She talks about embracing the messy early years of a career. She explains why building a craft matters more than chasing prestige. She explores how AI and impersonal hiring change job search and why relationships and cold outreach still matter.
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insights INSIGHT
Job Searching Has Become Lonelier Over Time
Insight: The application process has become lonelier and more impersonal with AI interviews replacing humans.
Jessi and Jodi note younger applicants face interviews by machines and reduced human feedback, increasing isolation.
volunteer_activism ADVICE
Lean Into A Fruitful Struggle
Do embrace a fruitful struggle instead of quitting early in the job search.
Jodi urges young people to persist through early career hardship so they don't forfeit long-term happiness and opportunity.
volunteer_activism ADVICE
Choose A Craft You Own
Do pursue a craft you can own because it outlasts jobs and market shifts.
Jodi Kantor advises finding a skill you love, are good at, and that fills a need so your craft remains yours even if jobs vanish.
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Finding your path to a meaningful career has never felt more complicated. The job market is entirely unpredictable, AI is reading your resume, and entire industries seem to be disappearing.
It’s a particularly uncertain moment to be entering the workforce for the first time. This week on Hello Monday, Jessi Hempel talks with Jodi Kantor about navigating the early years of a career.
Jodi is one of the Pulitzer Prize–winning journalists who broke the Harvey Weinstein story, igniting the Me Too movement. Last year, she delivered a commencement speech to Columbia’s class of 2025, offering practical and comforting advice for young people on the cusp of their professional lives. She’s expanded on that guidance in her new book, How to Start, which offers a roadmap to a meaningful career.
In this episode, Jessi and Jodi discuss:
Why the early stages of a career are inherently difficult, and how to embrace a “fruitful struggle” instead of giving up
Jodi’s own winding path, from law school dropout to journalist
How the job search itself has changed, including the rise of AI interviews and increasingly impersonal hiring processes
Why the real measure of a career isn’t prestige or stability, but how connected you feel to the work in your day-to-day tasks
The challenge of distinguishing your own voice and interests from expectations coming from parents, culture, or conventional career advice
Why trying to game the job market or chase the “safe” profession rarely works
How to hold onto the belief that work can be meaningful, satisfying, and sustainable, even in a difficult job market
How cold calling doesn’t get easier, and why you should do it anyway
This episode is for anyone starting out, starting over, or helping someone else navigate the messy early chapters of a career.
Hello Monday with Jessi Hempel 
