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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