How to Start Your Career When the Old Rules Don’t Apply

About this episode

Jessi Hempel talks with Jodi Kantor about navigating the early years of a career in an unpredictable job market.

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…

People in this episode

Hosts: Jessi Hempel, Jessi

Guest: Jodi Kantor

Topics covered

• career development
• job market
• AI in hiring
• Me Too movement
• personal growth

Keywords

• meaningful career
• fruitful struggle
• job search
• AI interviews
• personal voice

Mentioned in this episode

Products: How to Start

Books & works: Pulitzer Prize, How to Start

More episodes of Hello Monday with Jessi Hempel

• Lessons From a Year of Letting AI Do Everything · June 8, 2026 · 30 min
• Jenny Hagel on How to Build a Creative Career When the Odds Are Against You · June 1, 2026 · 29 min
• Bonus: Lesbian Bars and the Secret Formula for Belonging · May 28, 2026 · 15 min
• How to Build a Career You Actually Believe In · May 25, 2026 · 30 min
• We're Lonelier Than Ever. Ritual Is the Answer. · May 18, 2026 · 29 min
• Feed Drop: WorkLife with Molly Graham · May 14, 2026 · 40 min