Oct. 19, 2026

The Trap of Success: Why Working at a Successful Company Can Hurt Your Career

The Trap of Success: Why Working at a Successful Company Can Hurt Your Career
The Trap of Success: Why Working at a Successful Company Can Hurt Your Career
Per My Last Email
The Trap of Success: Why Working at a Successful Company Can Hurt Your Career

In this episode, Kaila and Kyle discuss the potential career pitfalls of working at a successful company, and how to avoid the “trap of success” when you do.

00:00 Intro

03:53 Kaila’s experience of leaning on Morning Brew’s success

06:52 Why it’s easy to get lazy at a successful company

09:19 The traps to be aware of at a successful company

14:45 How potential employers should analyze candidates from successful companies

16:56 Discussing the trap of success

22:51 A final note on the trap of success

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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!