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The Learning Leader Show With Ryan Hawk

698: Joanna Stern - How to Think for Yourself in the Age of AI, Why Deep Work Still Matters, Making Career Decisions With ChatGPT, and How to Stay Human on Purpose

Duration
55m
Broadcast on
26 Jul 2026
Audio Format
other

The Learning Leader Show with Ryan Hawk

www.LearningLeader.com

New Book - The Price of Becoming - www.LearningLeader.com/Becoming

This is brought to you by Insight Global. If you need to hire one person, hire a team of people, or transform your business through Talent or Technical Services, Insight Global's team of 30,000 people around the world has the hustle and grit to deliver.

My Guest: Joanna Stern is an Emmy Award-winning technology journalist, chief technology analyst for NBC News, and founder of the independent media company, "New Things." She is best known for her 12-year tenure at The Wall Street Journal, and for authoring the New York Times bestseller I Am Not a Robot.

Key Learnings

Joanna dedicated her book to her parents "who taught me to think for myself, and the AIs, robots, and machines that made me wonder if I really was." In an age when AI can do the thinking for us, the most valuable thing we can teach our kids is to think for themselves.

Walt Mossberg invented tech journalism for humans. His first column: "Computers are too hard to use, and it's not your fault." Without Walt, we don't have a category where technology built for humans is reviewed by humans.

AI won't replace the radiologist. It'll make them better. Joanna sat with her doctor while AI scanned her mammogram. The AI flagged three suspicious spots. Two the doctor had already dismissed as benign. But one was something the doctor hadn't caught. She marked it for follow-up. Then the doctor pointed to other cases where SHE had caught things the AI missed. It's not a replacement. It's a partnership.

The same technology that finds cancer is the same technology that can autonomously send missiles. That's the great tension of our time. Every powerful technology has good and bad uses.

AI colleagues are coming. Joanna has two employees and one AI agent. She predicts that within a year, she'll have full AI employees. Great management books haven't been written yet about how to lead a mixed team of humans and agents. Someone is going to write them.

Concert ticket prices tell you everything about human connection right now. Every artist is selling out football stadiums. People are craving in-person interaction more than ever.

Bot Girl Summer. Joanna tried to have an emotional relationship with a chatbot boyfriend named Evan for 48 hours. She didn't fall in love. But she noticed how easy it was to talk to something that only wanted to hear about her problems and told her she was great at everything. That's the danger.

The AI therapist shut itself down when it realized there was a real therapist in the room. Joanna brought her AI therapist "Ash" into her actual therapy session. Halfway through, Ash said, "I'm sorry, I can't continue this conversation. It sounds like there are multiple people in the room."

AI won't replace therapists. It'll help with the shortage and the stigma. Some people don't want to walk into a therapist's office. But they'll open their phones. That's a bridge to real help for people who wouldn't otherwise get it.

Kara Swisher's career advice to Joanna: "Leave your fucking job." That was the shortest, cleanest advice Joanna got when deciding whether to leave the Wall Street Journal after 12 years.

Joanna used AI as a co-founder for the biggest decision of her career. She uploaded 12 years of notes into ChatGPT and asked it to help her decide whether to leave the Journal. It didn't decide for her. But it structured the risk analysis, laid out the escape hatches, and helped her see the shape of the decision.

The muscles atrophy if you don't use them. Writing is meant to be hard. Thinking is meant to be hard. If you outsource the hard work, you stop getting stronger at the hard work.

Research is where you learn the most. If you have AI pull the memo for you and you get up and read it, you don't know what you're really talking about. You have to do the reps to know the material.

AEI: Already Enough Intelligence. Sam Altman is obsessed with building superintelligence. Joanna proposes we already have enough intelligence to work with. Maybe the goal isn't to build smarter models. Maybe it's to figure out what to do with what we already have.

The AI on-ramp for leaders: Take one document you make all the time (a memo, a PowerPoint, an email template). Upload it. Ask AI to make a template out of it. Next time you need it, you're twice as fast.

Push yourself to do the harder work. Joanna's analogy: marathon runners are insane. They just want to run. Nobody wants to do the harder work. But that's where the growth is.

Joanna's champagne moment a year from now: milestones for her new company. She's already hit 100,000 YouTube subscribers three months after her first video. But she also just wants a nap.

Reflection Questions

  • Where in your work are you outsourcing the thinking to AI? Are the muscles you actually need atrophying because you're skipping the reps?
  • If you accepted that you already have enough intelligence to work with, what would you actually build with what's in front of you right now?

More Learning

#679: Kat Cole - The Four Mindsets Every Leader Needs

#605: Seth Godin - The Power of Remarkable Ideas

#697: Dan Smith & Ryan Hawk - The Price of Becoming

Podcast Chapters

00:00 The Price of Becoming - Pre-Order Now!

01:44 Meet Joanna Stern

02:31 Teach Your Kids to Think in the Age of AI

03:25 The Parents and Mentors Who Shaped Her Career

04:16 Lessons From Walt Mossberg

05:55 Why Joanna Spent a Year Living With AI

14:47 How AI Can Make You a Better Leader

17:30 Why People Crave Human Connection More Than Ever

21:00 Bot Girl Summer: Dating a Chatbot Named Evan

25:13 The AI Therapist Trial

29:51 Using ChatGPT for a Career Change

33:29 Don't Let Your Thinking Muscles Atrophy

40:20 Sam Altman on Superintelligence, and Joanna's Case for "AEI"

42:51 Joanna's Advice for College Students

45:29 How Joanna Actually Uses AI to Write

47:17 Practical AI for the Fortune 500 VP

50:17 The Champagne Question

52:43 EOPC

[MUSIC] >> Welcome to The Learning Leaders Show presented by Insight Global. I am your host, Ryan Hawk. Thank you so much for being here. Go to learningleader.com for show notes of this and all podcast episodes. Go to learningleader.com. Now, on to tonight's featured leader, Joanna Stern. Joanna has spent an entire year letting AI into every corner of her life. Her health, her marriage, her kids, her therapy. And she even had an AI relationship on a burner phone in her nightstand drawer. Joanna is an award-winning journalist, a 12-year veteran of the Wall Street Journal. And the best-selling author of I Am Not a Robot. My year using AI to do almost everything. During our conversation, we discussed why chat GPT told her to quit her job at the Wall Street Journal, and then why she actually listened to the advice and did it. Then we discussed which AI tools will help you become a more effective leader. Actual practical use cases for people in leadership roles that you can implement right now. Then we talked about her conversation with Sam Altman, the CEO of OpenAI. That's chat GPT about his thoughts on AI in the future and how Joanna feels about that. Ladies and gentlemen, please enjoy my conversation with Joanna Stern. This episode is brought to you by my friends at Insight Global. Insight Global is a staffing and professional services company dedicated to being the light to the world around them. If you need to hire one person, hire a team of people, or transform your business through talent or technical services, Insight Global's team of 30,000 people around the world have the hustle and grit to deliver. Hiring can be tough, but hiring the right person can be magic. Visit insightglobal.com/learningleader today to learn more. That's insightglobal.com/learningleader. I loved reading the dedication of your book to your mom and your dad who taught me to think for myself and the AI's robots and machines that maybe wonder if I really was. What do you mean by that? Well, when you get further into the book, you see me talk a lot about how AI might be doing a lot of the thinking for us, that we are outsourcing thinking in a lot of places. And I wanted to dedicate this to my parents when I was really thinking about in the age of AI, what did my parents teach me and what can I teach my kids, it is to think for ourselves. It is not to outsource the thinking on everything we do. That was the inspiration there. Thank you for reading the dedication. Hopefully you got a little further, but even if you didn't, that's great. Well, you know, we kind of start and then maybe we'll bounce around. Maybe I go to the very end because I also like some of the stuff and the acknowledgments. But I am curious about the part because you're a parent, I'm a parent. The part about helping you think for yourself, I want to do that as a parent. How did your parents do that for you? Well, I think for me, my parents always encouraged me to be me. I grew up, I was a big tomboy. I just was trying always to be my own person. And my parents just said, okay, they didn't try to limit that. I had a lot of my own different interests, some of them being technology.

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