Oct. 5, 2026

The “Enshittification” of Work: Why Your Career Feels Broken

The “Enshittification” of Work: Why Your Career Feels Broken

In this episode, Kaila and Kyle dive into Kaila’s theory that we’re seeing the “enshittification” of work, and how it is impacting the job market, college, and the career ladder. Listen to hear them explain the theory, and discuss what you as either a job-holder or job-seeker can do about it.

00:00 Intro

01:24 Where the inspiration for this topic came from

05:13 What we mean by “enshittification”

11:13 The promise we were sold of college

15:49 The “planned obsolescence” of the career ladder

18:50 The messiness of the job market

25:54 Advice for navigating the “enshittification” of work

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Each week on Per My Last Email, Morning Brew’s resident career experts Kaila and Kyle – whose careers have collectively spanned the corporate, government, nonprofit and startup sectors – debate the trickiest challenges in work life, and share tactics on how to overcome them. Share the show with a friend, and leave us a review on your favorite podcast app!