Will you still have a job in five years?
Zack Kass, a former OpenAI executive and 16-year AI veteran, joins us to unpack the question that keeps many knowledge workers awake at night. But instead of focusing on layoffs or wages, Zack reframes the conversation around something deeper and more unsettling: identity.
We want faster legal services, cheaper healthcare, and more efficient systems, yet we resist automation when it threatens our own roles. Zack argues this contradiction reveals a looming identity crisis that could eclipse any economic disruption caused by AI.
In this episode, we explore which jobs are most vulnerable, which may actually benefit from AI, and why financial illiteracy quietly costs people far more than automation ever has. We also discuss why housing, healthcare, and education remain stubbornly expensive, how AI could reshape access to basic needs, and what it means to build a meaningful life when work no longer defines us.
This isn’t a doom-and-gloom conversation about machines taking over. It’s a practical, human look at how automation could free up time, creativity, and community, if we’re willing to rethink our relationship with work, money, and screens.
Key Takeaways
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We want automation everywhere except our own jobs, creating resistance that has more to do with identity than economics.
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The real threat of AI is not unemployment, but our inability to separate self-worth from work.
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Financial illiteracy quietly drains wealth through fees and debt, and AI could help people make smarter money decisions if used well.
Resources
Zack’s website
The next renaissance newsletter
The Next Renaissance (Book by Zack Kass)
Related podcast
Chapters
Note: Timestamps are approximate and may vary across listening platforms due to dynamically inserted ads.
(0:00) Introduction
(2:00) Zack’s background in AI
(3:15) Will knowledge workers still have jobs?
(9:06) Why we want other people’s jobs automated
(10:14) The identity crisis behind job fears
(50:55) Financial illiteracy and hidden costs
(1:03:51) Why housing, healthcare, and education stay expensive
(1:18:31) Screen time and the illusion of busyness
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