Now to Next | Jason Averbook | Substack

“I’d Rather Talk to a Human”: Why That Reaction Needs a Reset

If you're still judging AI by a bad chatbot from 2018, you're not reacting to the future—you're reacting to the past.

Jun 3 •

Recent posts

10:59

Live with Jason Averbook

A recording from Jason Averbook's live video

May 30 •

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I’m Afraid We’re About to Make the Same Mistake With AI We’ve Made Before

We’re moving faster than ever—but in what direction?

May 29 •

Before ChatGPT, There Was Clippy: The Rise, Fall, and Surprising Resurrection of Computing's Most Hated Helper

How a goofy animated paperclip pioneered the AI assistant—and taught us what not to do along the way.

May 26 •

Your Employees Are Already Using AI. Your Strategy Still Thinks It’s 2019.

How business transformation in 2025 demands rethinking leadership, decision power, and what it means to truly keep up.

May 22 •

Yes, AI Is Unsettling — That’s Why It Matters

We don’t need leaders who pretend to be fearless. We need leaders who know how to move forward with fear — and bring others with them.

May 18 •

Pretending Work Hasn’t Changed Is the Biggest Risk of All

The reinvention of work isn’t on the horizon—it’s already here. HR is on the front line, and it’s time to choose: design the future or get designed…

May 12 •

The Death of Search: Why Generative AI Is the Future of Finding Answers Both at Work and in Life.

The future of work isn’t about searching better—it’s about not needing to search at all.

May 11 •

Stop Calling It Cheating

The Real Debate Behind AI in Work, School, and Life

May 4 •

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