Why Awkwardness Is a Career Superpower, Overcoming Social Discomfort, and Building Confidence

We’ve all had those painfully awkward moments–those cringey, uncomfortable feelings—the ones that make you want to disappear into the floor. But what if awkwardness wasn’t something to escape, but something to embrace? Today, I sit down with workplace performance expert Henna Pryor to unpack why discomfort is actually a good thing.

Henna shares her personal journey from feeling like an outsider as a child of immigrants to discovering how awkwardness can be a growth accelerator. She also reveals surprising research on why confident people don’t avoid awkward moments—they just recover faster. Plus, we dig into how social skills are eroding in the workplace, why millennials report the most superficial relationships at work, and how different generations handle awkwardness.

If you’ve ever second-guessed yourself before speaking up in a meeting, hesitated before trying something new, or let fear of embarrassment hold you back, this episode will change the way you think about discomfort.

If this episode gave you the push to stop overthinking and embrace the cringe, share it with a friend! And if you really loved it, we’d be forever grateful if you left us a review on Apple Podcasts. It helps more people find the show (and helps us keep embracing our awkward too).

“In our 20s and 30s, we care a lot about what people think of us. In our 40s and 50s, we stop caring what other people think of us. But in our 60s and 70s, we realize they were never thinking about us in the first place, and that knowledge is so freeing.”
~ Henna Pryor

In This Episode:
00:00 - Introduction
01:33 - Why awkwardness isn’t a curse but a superpower
04:14 - Henna’s childhood struggles with feeling different
09:08 - How age shifts our self-consciousness (and makes us care less)
14:28 - The workplace “social muscle” problem across generations
20:01 - Remote work + tech = weaker social skills (and it shows)
23:56 - 86% of workers would rather work alone—yikes
26:25 - Small steps to build social confidence without freaking out
28:04 - Using humor to recover from awkward moments
29:54 - Risk-taking at work: when to go for it and when to hold back
32:32 - The “Cringe Chasm”—choosing between comfort and growth
36:33 - The worst-case scenario exercise that flips fear on its head

Resources:
Book: Good Awkward by Henna Pryor: https://pryoritygroup.com/book/
The Social Muscle Study: Download the full report at https://pryoritygroup.com/study/
Henna’s TEDx Talk: https://www.ted.com/talks/henna_pryor...

Connect with Henna Pryor:
Website: https://pryoritygroup.com/
LinkedIn:   / hennapryor  

Connect with Maureen Wiley Clough:
LinkedIn:   / maureenwclough  
Website: https://www.itgetslateearly.com/
Instagram:   / itgetslateearly  
Facebook:   / 100088694515585  

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