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Simplify · Today · 13 min

Simplify EXTRA: The Human Premium

Why do commencement speeches suck so often? That's easy. They suck when the speaker is out of touch with their audience - new graduates. That's why legendary ones like from David Foster Wallace and George Saunders and Steve Jobs are so good, because they balance personal experience in a way that connects with a new generation. This year, multiple tech CEO commencement speakers were booed across the US for being so out of touch with new grads' realities. When you’ve spent four years paying up for a degree, hearing an ultra-wealthy AI sponsor tell you to "get on the rocket ship" or whatever while the entry-level job market evaporates feels less like inspiration and more like an insult. Honestly, I'm proud of the grads for booing. In this second edition of our new format - we're calling it Simplify EXTRA - we look at why traditional career advice is failing Gen Z, and what a genuinely useful path forward looks like. Ben drives this episode and brought Caitlin Jasmine Sun’s Substack article, 🌻 the old world is dying: opinionated advice for c/o 2026 graduates which offers some tips from one Gen Zer to other Gen Zers toward building a meaningful life when the old rules no longer apply. Then Caitlin and Ben trade some life advice and share what they think future grads need to hear. And yes, we’re still testing out our new video format! We’re tweaking the studio setup, playing with lighting, and dialing in the camera angles, so please send us your feedback - we’d love to know what you think. Resources Jasmine Sun's article Bill Burnett - designing your life Email us at info@kollomedia.com Simplify on YouTube Simplify on Instagram Subscribe to our newsletter here. This episode was produced by Caitlin Schiller, Molly Rose Hart, and Ben Schuman-Stoler. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Why do commencement speeches suck so often? That's easy. They suck when the speaker is out of touch with their audience - new graduates. That's why legendary ones like from David Foster Wallace and George Saunders and Steve Jobs are so good, because they balance personal experience in a way that connects with a new generation.

This year, multiple tech CEO commencement speakers were booed across the US for being so out of touch with new grads' realities. When you’ve spent four years paying up for a degree, hearing an ultra-wealthy AI sponsor tell you to "get on the rocket ship" or whatever while the entry-level job market evaporates feels less like inspiration and more like an insult. Honestly, I'm proud of the grads for booing.

In this second edition of our new format - we're calling it Simplify EXTRA - we look at why traditional career advice is failing Gen Z, and what a genuinely useful path forward looks like. Ben drives this episode and brought Caitlin Jasmine Sun’s Substack article, 🌻 the old world is dying: opinionated advice for c/o 2026 graduates which offers some tips from one Gen Zer to other Gen Zers toward building a meaningful life when the old rules no longer apply.

Then Caitlin and Ben trade some life advice and share what they think future grads need to hear.

And yes, we’re still testing out our new video format! We’re tweaking the studio setup, playing with lighting, and dialing in the camera angles, so please send us your feedback - we’d love to know what you think.

Resources


This episode was produced by Caitlin Schiller, Molly Rose Hart, and Ben Schuman-Stoler.

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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