Sept. 22, 2025

Is it Cringe to Try Hard at Work?

Is it Cringe to Try Hard at Work?

Is it cringe to try too hard? In this episode, Kaila and Kyle are joined by Normal Gossip co-creator and Defector Media co-owner Alex Sujong Laughlin to talk about the ins and outs of being a “try hard” at work. Alex’s new podcast, Try Hard, documents people attempting things that they’re afraid to do, and in this episode you’ll hear about a couple of moments when Alex and Kaila’s fear of being cringe nearly held back their career progress.

00:00 Intro

01:40 What is “Try Hard”?

05:29 Why being a “try hard” in the office is perceived as cringe right now

12:33 An experience that almost derailed Alex’s career path

17:18 How to gently encourage trying hard

21:33 What’s the right level of earnestness at work?

25:42 Is LinkedIn posting cringe?

28:09 A time where Kaila’s fear of being “cringe” almost held her back in her career

This episode was sponsored by Udemy. Try a free 14-day trial at Udemy now at udemy.com/personal-plan and use code PMLE14.

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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!

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