I wanted to take a bit of a different tack with this one. Shorter. More of a story we can all share and talk about.
This one just felt like it needed to be free as the birds and open as the sky.
Hope you enjoy!
I think we'll call him Josh. Josh isn't real. Josh is an amalgamation of a lot of different stories that I've been privileged to be a part of over the last year or two, often in a small way, often overheard in a cocktail lounge or through a conversation with a colleague or in a few cases, one-on-one talking about work and life. Sometimes at a conference, sometimes at home, sometimes on the phone, sometimes out in the world walking around where people talk about AI.
Josh's story is about AI. So many of our stories are about AI right now. And the reason I'm sharing this story is because I don't think Josh's story gets shared enough.
Meet Josh
Josh is a guy who got a good college education—he got a journalism degree. He has a little bit of college debt left, not a lot. And he had hoped, as many hope who get into journalism and liberal arts, to make a career for himself from a media perspective. He'd hoped to be a celebrated columnist one day.
He got his start at a very small internet newsroom that got shut down very quickly when AI came along. And Josh will tell you: "AI took my job." Full stop.
Josh never really got the chance for his career to upshift because he graduated in 2018. He didn't have more than a couple of years of experience in the newsroom. And then COVID hit and things shifted. And then after COVID hit, AI hit and Josh feels like he's been taking it on the chin for a long, long time.
When Josh hears advice like, "hey, you should vibe code," he just kind of rolls his eyes. That's not what he set out to do. That's not what he's passionate about. He got into journalism to tell stories. He wants to tell people's stories.
Josh’s Dreams on Ice
Josh has a small, fragile dream. He wants to tell the stories of how people's lives are changing in tangible ways because of AI. But Josh is at a local minima, which is a fancy way of saying he is stuck. Josh can't get the equipment that he needs for the podcast studio of his dreams, and (much more important) Josh can't get the contacts that he needs to set up the conversations he’d like to have. That’s the expensive part (but not in money)—Josh is out of the network he needs to be in to have the conversations he’d need to have to get his dream on track.
The dream feels like it’s dying before it gets off the ground, and Josh is struggling to care because he has to make his college debt payment and since when did an ordinary guy’s podcast pay enough for that? The dream he has just doesn’t feel viable anymore.
Josh has moved back home with his parents to Vermont. He's settled in and he's not sure where his career is going at this point. And all the AI coursework that he can find—and he does a little bit of learning online—isn't really helping him move forward.
Josh doesn't see AI as an enabler. Far from it. Josh rolls his eyes when people talk about AI helping. All Josh sees is obstacles created by AI, frankly. AI is the one that took Josh's job away. AI is the one that killed Josh’s career. And Josh isn’t shy about saying so.
Why Josh's Story Matters
I share Josh's story because as much as I like to talk a lot about the potential that we all have to unleash with AI, I don't want to miss out on the difficult stories. I don't want to miss out on the challenging stories, the stories that don't fit as easily into that narrative of progress. And the reality is, with any story of technical change, there are stories like Josh's.
Sidebar: One of the things that isn’t helpful is connecting the dots at this point. I could spend a few hundred words painting the story of the changing macro-economics of media over the last decade prior to AI and then eventually tie that larger industrial change in how we tell stories to Josh’s experience—but Josh doesn’t want to hear that.
In 2025, a lot of the responsibility that we carry as a society is to think about how we can support the Joshes of this world. Not support them in the sense of giving them a handout—I don't think Josh is interested in that either. I'm talking about helping Josh find a place where he knows that he's valued for the contributions he can bring, the passion he has for telling stories in this world.
This is where it would be nice to have a silver bullet. I have a lot of bronze bullets—tactical helps that I can pull out and try. But there are no universal answers. And I find reaching for tactical tips is often the last thing the Joshes I speak to want.
When you’re feeling lost because of AI, just listening is the first job.
What Do We Say to Josh?
Now, to be honest Josh is sometimes not an easy person to help. Josh doesn't want a handout. Josh is suspicious if you try to give him advice. Josh resents AI to the point where if you recommend a practical solution to him that might help, he's gonna say no. From his point of view, he’s correct.
And that makes it difficult, because even options that are positive and helpful for Josh can be perceived as threatening.
I want to suggest that the only way to get past that, to get to the tactical help you might have in mind, is to start with an honest question:
Are you open to having an honest conversation about the idea that the game board has changed, you're right about that.
The rules of the game have changed a bit, you're right about that.
But there still may be a space for you and your talents and your passion that you bring, even if it's not what you originally imagined. Are you open to your dreams shifting?
That's the thing at the root that I think we need to talk about. And that's not really an AI conversation. And I share that because that feels like that's a conversation many of us who are interested in AI, who are passionate about AI, need to be having with those around us.
I see the poll results. I see that AI is not trusted. There are a lot of Joshes in this world. It makes sense that they may not trust AI. I don't blame them. It's kind of rational. But in that world, we have to be the ones—we who are interested in AI have to be the ones who are able to sit down and invite a conversation about how all of our dreams are changing because of AI.
That's not something that anybody is immune to, including me!
My Own Story of Change
And so besides telling Josh's story, I'll tell my own story a little bit. I got my start in a job that AI has changed dramatically. I was doing nonprofit grant management. AI can do a lot of the work that I was doing at the push of a button.
Then I went over to Oracle iStore management and conversion optimization. Conversion optimization doesn't exist as a job anymore, really. Not even on LinkedIn. AI took it away. And iStore—I mean, who has Oracle iStore anymore? I'm sure someone's gonna comment, "I have Oracle iStore" after I publish this, but it’s not much of a job anymore.
And then after that I went and did marketing and I looked at marketing attribution systems. Again, another area where AI has taken a lot of the work away. I looked at voice of customer at Amazon—almost totally automated by AI now.
You get the idea.
And what's funny as I look at that list is that even though AI has made huge strides, we still have people who handle grants, although now it’s often wrapped into a fundraising title. We still have people who are working in web production and how to make excellent experiences on the web, which is basically what conversion optimization does. We still have people who are focused on e-commerce management online, which is what I was doing with iStore. We still have people who are focused on learning from the voice of the customer, which would be what I was doing when I was later in my career at Amazon. We still have people who are focused on marketing and understanding marketing data.
Those functions still have humans doing important work in those areas, but many of the individual day-to-day skills ended up getting peeled away. And that's one of the really interesting things about the nature of work that I think we need to talk about more honestly with ourselves, with those around us, and with the Joshes in our lives.
The Flexibility to Dream Differently
If I had stuck with any individual dream, if I had told myself, "I'm gonna be a marketer and I'm just gonna do marketing," or "I'm going to be in conversion optimization and get really good at that," or more recently, "I'm gonna be in product management and get really good at that," I would have given myself a constraint on my dreams that I did not need to have.
I would have set myself up with artificial constraints. I would have put myself in a box.
Instead, I've been focused on this:
What are problems that I can run after solving as hard as I can?
How can I figure out how to add value against those problem spaces even if it feels scrappy today, even if it feels kludgy, even if it feels awkward, even if it feels like I'm not doing a great job because I'm new at approaching the problem in this new way?
Where do my dreams need to be held lightly because my world is changing really fast?
Here’s one that’s changed for me: I’m probably never going to be a CPO now. That job role is starting to become an endangered species as product teams evolve rapidly.
And that’s after investing a lot in the product career ladder, after feeling the pain of starting rough in the job family. When I was first getting into product management, I felt really awkward. My PRD instincts weren’t there. My voice of customer instincts were off. I didn’t know how to handle stakeholders well.
Zooming back, when I was first getting into the professional workplace decades ago, I had the exact same feeling. I felt awkward. I felt like I didn't fit. I felt like my professional skills were rusty because they'd never been used.
Every time I learn a new skill, it's like that. Every time I begin again, it's like that. When I first started putting videos up online, it was like that. And it's especially painful because that rough beginning is also the moment our dreams are in flux and evolving, so we can feel lost. That's the moment our dreams have to change because we learn the realities of the world we’re entering. And it doesn’t match our expectations.
As an example of dreams changing, even before AI: in PM we learn the bitter reality that if you are in a particular product management role for a while, there's no guarantee that you are really going to progress in your career. Especially above Senior PM, it gets very iffy. I think you’ll find similar hidden ceilings everywhere, and those change our dreams too.
AI as an Enabler of New Dreams
And the thing that AI enables us to do in this world that has been hard at every other point in human history is it enables us to dream differently.
It gives us more flexibility on our dreaming. It gives us the ability to stretch our wings in new areas very easily. It's an incredible teaching tool, yes. It's also a tool that enables us to practice our skills confidently.
We can practice our interview skills if that's what we're working on.
We can practice our coding skills if that's what we're working on.
We can get someone to help us read a new book and learn a new skill set from that book. If you want to learn the Why Machines Learn textbook by Anil—you can do that. You can literally take a picture of a complicated diagram that you don't understand, and you can get AI to help you learn it. And that's just an example on my bookshelf. You'll have others on your bookshelf.
I know that "Red Bull gives you wings" is trademarked. I know we can't say "AI gives you wings," but that's the vibe. Especially because those Red Bull videos are always absolutely terrifying.
And one of the things that I would like us to be able to do is to be honest about the fact that even though AI gives us a lot of flexibility, it gives us a lot of upside, it does mean a different world. It means our dreams are gonna be different because the world around us is changing so fast.
The New World of Work
I do not expect product management to be the same discipline in a year, two years. It's already changing really, really fast. People are looking for builders of all kinds and they are increasingly less looking for particular defined roles that have particular defined expertise chains in a particular job family. And that is leading to a lot of confusion and heartache.
That is why major companies can say AI automation engineers can apply to literally any job in the company.
The new world is a confusing place. It’s not getting less confusing.
And so my encouragement is, if you have a Josh in your life, find a way to gently ask if they're open to having a conversation about the idea that they might be welcome, useful, loved at work—their passion is important—but their dreams might need to shift.
And maybe ask yourself that too. Where do your dreams need to shift? Because AI is coming for us all—not (I don’t think) coming in the SkyNet sense, but coming in the sense of changing everything about the way we work, changing how we interact in our personal lives, changing how we are able to get from where we are today to where our dreams might be, and along the way changing where those dreams end up.
The Trade-Off We Live With
This is the trade-off we live with. We've taught the sand to think (approximately), but because the sand thinks, everything is different now. And so it's up to us to figure out how to turn this new cognitive revolution into something that we can all participate in and all enjoy and all live with.
And if that sounds really kumbaya, feel free to roll your eyes, but it's a real conversation that we need to have. And the more we roll our eyes and step away from it, especially with the Joshes of this world, the more we create a society where some people feel really left out on AI and really angry about AI, that is not a society I wanna live in.
So talk to the Joshes in your life, and let’s talk together about how dreams are shifting in the age of AI.
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