It Gets Late Early: Ageism in the Workplace

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


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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:

-Why awkwardness isn’t a curse but a superpower

-Henna’s childhood struggles with feeling different

-How age shifts our self-consciousness (and makes us care less)

-The workplace “social muscle” problem across generations

-Remote work + tech = weaker social skills (and it shows)

-86% of workers would rather work alone—yikes

-Small steps to build social confidence without freaking out

-Using humor to recover from awkward moments

-Risk-taking at work: when to go for it and when to hold back

-The “Cringe Chasm”—choosing between comfort and growth

-The worst-case scenario exercise that flips fear on its head

And much more!


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_want_to_get_ahead_at_work_risk_the_awkward_moments


Connect with Henna Pryor:

-Website: https://pryoritygroup.com/

-LinkedIn: https://www.linkedin.com/in/hennapryor/


Connect with Maureen Clough:

-LinkedIn: maureenwclough - https://www.linkedin.com/in/maureenwclough/

-Website: itgetslateearly.com - https://www.itgetslateearly.com/

-Instagram: @itgetslateearly - https://www.instagram.com/itgetslateearly/

-YouTube: @itgetslateearly - https://www.youtube.com/channel/UCGrHwk-y7ERaq7bCSjZYf1A?sub_confirmation=1

-Facebook: It Gets Late Early - https://www.facebook.com/people/It-gets-late-early/100088694515585/

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It Gets Late Early: Ageism in the WorkplaceBy Maureen Wiley Clough

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