Reinvesting in physical communities

Zack urges policy and local action to rebuild walkable, engaging physical spaces to combat isolation.

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#679: Will you still have a job in five years? Zack Kass, former OpenAI executive and 16-year AI veteran, joins us to tackle the question that keeps knowledge workers up at night.

Most people worry about the economics — who can pay the bills if AI takes their job? Kass flips the question: What happens when work no longer defines who you are? He argues we're heading for an identity crisis bigger than any economic disruption.

In this conversation, Kass explains why everyone wants everyone else's job automated (faster legal services, cheaper healthcare) but nobody wants their own work to disappear.

He shares why some jobs will vanish while others explode in demand, and which professions might actually benefit from AI disruption.

You'll discover why the real threat isn't job loss — it's that we've become addicted to our devices and forgotten how to live without constant work.

Kass reveals how financial illiteracy keeps people trapped in debt cycles that AI could help break.

He explains why housing, healthcare, and education costs stay high while everything else gets cheaper, and what might finally change that dynamic.

The conversation explores what happens when AI makes basic needs affordable for everyone.

Kass predicts some people will pursue passion projects, others will double down on work, and many will struggle to answer a simple question: What do you actually want to do with your day?

We discuss practical realities like how a 53-year-old attorney might reinvent herself, why accountants face bigger challenges than lawyers, and which human skills will become more valuable as machines get smarter.

Kass shares his theory about competing on kindness rather than intelligence when AI can outthink us all.

This isn't another doom-and-gloom AI prediction. Kass makes a compelling case that automation could free us to rediscover community, creativity, and purpose … if we can get past our addiction to both work and screens long enough to imagine what that life looks like.

Timestamps:

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 (0:00) Introduction

(2:00) Zack's AI background at OpenAI

(3:15) Will knowledge workers have jobs

(4:52) Job automation is complex

(7:53) Longshoremen strike over automation

(9:06) Everyone wants others' jobs automated

(10:14) Identity crisis bigger than economics

(13:36) Lawyers might enjoy job loss

(21:42) Societal thresholds stop automation

(28:52) Bespoke services always find demand

(41:34) AI won't replace human therapists

(47:11) Dehumanization threatens physical connections