Hello Monday with Jessi Hempel

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

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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.

    Follow Jodi Kantor and Jessi Hempel on LinkedIn

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