Author on designing a life without labels  episode artwork

EPISODE · Mar 10, 2026 · 38 MIN

Author on designing a life without labels

from The Unemployment Diaries · host Aisha Ommaya

What if the question "so, what do you do?" is the wrong question entirely?Charlie Rogers never had a conventional answer because he never took the conventional path. He built and closed businesses, represented Great Britain in triathlon, and spent the last decade figuring out how to live beyond labels. Now he's written the field guide for everyone else who's ever felt too much for one box.In this episode, Charlie shares his story and:Why "what do you do?" asks you to delete parts of yourself How to strip away inherited assumptions about how life "should" look and rebuild from zeroWhy the echo chambers we live in keep us smaller than we need to beThe Purpose Acropolis framework and how to find your golden threadWhy focused experts earn twice as much as generalists — and how Undefinables can have it both waysThe advice he'd give anyone who has more interests than they know what to do withChapters00:00 Meet Charlie Rogers00:49 So, what do you do?03:51 Charlie's unconventional background08:18 How do you know it's time to move on?09:22 What is a golden thread?12:55 We're not one thing forever13:34 Can you be an expert with many interests?17:39 When life goes out of balance19:58 How constraints shape your future22:36 How to shift your mindset24:21 Is it growing pains or just pain?31:38 From "good enough" to "great"35:41 Advice for younger CharlieWhere to find Charliehttps://www.undefinablelifedesign.com/SubstackBuy the book on AmazonFor more from The Unemployment DiariesStay up to date on InstagramGo behind the scenes on SubstackWatch on YouTube

What if the question "so, what do you do?" is the wrong question entirely?Charlie Rogers never had a conventional answer because he never took the conventional path. He built and closed businesses, represented Great Britain in triathlon, and spent the last decade figuring out how to live beyond labels. Now he's written the field guide for everyone else who's ever felt too much for one box.In this episode, Charlie shares his story and:Why "what do you do?" asks you to delete parts of yourself How to strip away inherited assumptions about how life "should" look and rebuild from zeroWhy the echo chambers we live in keep us smaller than we need to beThe Purpose Acropolis framework and how to find your golden threadWhy focused experts earn twice as much as generalists — and how Undefinables can have it both waysThe advice he'd give anyone who has more interests than they know what to do withChapters00:00 Meet Charlie Rogers00:49 So, what do you do?03:51 Charlie's unconventional background08:18 How do you know it's time to move on?09:22 What is a golden thread?12:55 We're not one thing forever13:34 Can you be an expert with many interests?17:39 When life goes out of balance19:58 How constraints shape your future22:36 How to shift your mindset24:21 Is it growing pains or just pain?31:38 From "good enough" to "great"35:41 Advice for younger CharlieWhere to find Charliehttps://www.undefinablelifedesign.com/SubstackBuy the book on AmazonFor more from The Unemployment DiariesStay up to date on InstagramGo behind the scenes on SubstackWatch on YouTube

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Author on designing a life without labels

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This episode was published on March 10, 2026.

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What if the question "so, what do you do?" is the wrong question entirely?Charlie Rogers never had a conventional answer because he never took the conventional path. He built and closed businesses, represented Great Britain in triathlon, and spent...

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