Are we Prepared for what Comes Next?
Look, I’ve been covering markets and corporate America long enough to know when something shifts from background noise to a real moment. And we’re in one of those moments right now with AI and jobs.
Just last week, Block announced they’re trimming their workforce—again—with AI playing a starring role in the decision. Citi’s been pretty upfront about it too, talking openly about how automation is going to reshape their headcount over the next few years. And they’re not alone. Not even close.
I’ve written about this before, sure. We all have. But here’s what’s different now: the pace. It used to be that we’d hear about one big company making AI-driven workforce changes every few months. Now? It feels like every week there’s another earnings call, another memo, another quiet restructuring where AI is doing work that people used to do.
And that drumbeat? It’s creating something I’m seeing more and more in conversations with workers, executives, and even my own colleagues—anxiety. Real, tangible, keep-you-up-at-night anxiety about what happens next.
Is This Your Standard Automation Story?
Here’s the thing that makes this different from every other wave of automation we’ve seen: AI isn’t just coming for repetitive, manual tasks anymore. It’s not just factory floors or call centers (though it’s definitely still coming for those).
We’re watching AI take on work that, frankly, a lot of white-collar workers thought was safe. Content creation. Financial analysis. Legal research. Customer service management. Even coding, which was supposed to be the safe career path everyone pivoted to over the last decade.
I was talking to a friend who works in marketing at a Fortune 500 company. She’s good at her job—really good. But her team of twelve is now down to seven, and they’re producing more content than ever. How? ChatGPT, Jasper, and a handful of other AI tools are doing the heavy lifting on first drafts, social media posts, and email campaigns. She’s not worried about her job today, but she’s worried about her job in two years. And she’s not wrong to be.
Block and Citi Wake-Up Call
When Block announced their latest round of cuts, the company was pretty transparent about it. They’re not hiding behind vague corporate speak about “operational efficiencies.” They’re saying it plainly: AI is allowing them to do more with fewer people.
Citi’s been even more direct. CEO Jane Fraser has talked openly about using technology to eliminate roles, with targets to cut tens of thousands of positions over the next couple of years. Some of that is typical bank restructuring, sure. But a huge chunk of it is about automation and AI taking over tasks that used to require human judgment.
And here’s what’s keeping people up at night: if companies like Block and Citi—massive, sophisticated organizations with deep pockets and long-term thinking—are making these moves now, what does that signal to everyone else? It signals that this is real. That this is happening. That the future a lot of tech evangelists were talking about in abstract terms is actually here.
Anxiety Is Spreading (And It’s Rational)
I want to be clear about something: the anxiety people are feeling about AI and their jobs isn’t irrational panic. It’s not Luddite fear-mongering. It’s a rational response to watching the employment landscape shift in real time.
When you’re in your thirties or forties, maybe you’ve got a mortgage, kids, student loans you’re still paying off, and suddenly the skills that got you to where you are don’t feel like enough anymore, that’s legitimately scary. You can’t just retrain overnight. You can’t pivot your entire career on a dime, especially when you’ve got obligations and people depending on you.
And let’s be honest: the advice coming from the top isn’t exactly reassuring. “Learn to work alongside AI!” “Become AI-literate!” “Focus on skills AI can’t replicate!”
Okay, great. But what does that actually mean when you’re a mid-level analyst at a bank and you’re watching AI models do in seconds what used to take you hours? What does it mean when you’re a paralegal and AI can review thousands of documents faster and more accurately than you ever could?
Productivity Paradox Nobody’s Talking About
Here’s something that’s not getting enough attention in all of this: companies are getting more productive with AI, but workers aren’t necessarily seeing the benefits of that productivity in their paychecks or job security.
Normally, when companies become more efficient, there’s at least a theory that some of those gains trickle down—maybe in the form of higher wages, better benefits, or more job opportunities in new areas. But what we’re seeing with AI is different. The productivity gains are going straight to the bottom line, and headcount is going down, not up.
Block can do more with fewer employees. Citi can process more transactions with a smaller workforce. And shareholders love it because it means better margins and higher stock prices. But if you’re one of the employees who’s no longer needed? You’re not sharing in those gains. You’re updating your resume.
Junior Employee Risks
There’s another angle to this that I think is going to bite us harder than we realize: AI is eliminating a lot of entry-level and junior positions. The jobs where people used to learn the ropes, make mistakes, develop judgment, and work their way up.
Think about law firms. Junior associates used to spend years doing document review, legal research, drafting memos—grunt work, sure, but work that taught them how to think like lawyers. AI can do a lot of that now, faster and cheaper. So firms are hiring fewer junior associates.
Same thing in finance. Junior analysts used to build models, pull together pitch decks, do comps. Now AI tools can generate a lot of that automatically. So banks are hiring smaller analyst classes.
Where does that leave the next generation? How do you develop expertise if the entry-level jobs that used to be the training ground don’t exist anymore? How do you build a career ladder when the bottom rungs are being systematically removed?
Nobody has a good answer to that yet, and it’s troubling.
What Companies Are (And Aren’t) Saying
Most companies are being pretty careful with their messaging around AI and jobs. They’ll talk about “augmentation” rather than “replacement.” They’ll emphasize new opportunities and upskilling programs. They’ll point to roles that AI creates rather than the roles it eliminates.
And look, some of that is true. AI will create new jobs. It already has. Prompt engineers, AI trainers, machine learning ops specialists—these are real roles that didn’t exist five years ago.
But let’s not kid ourselves: the math doesn’t add up. For every new AI-related job that gets created, multiple traditional jobs are going away. And the new jobs often require different skills, different education, different backgrounds than the jobs being eliminated.
A customer service rep who loses their job to an AI chatbot isn’t automatically qualified to become a machine learning engineer. The transition isn’t that simple, and pretending it is does everyone a disservice.
Policy Talk
What’s making the anxiety worse is that there’s no clear policy response taking shape. No safety net being built for this specific transition. No large-scale retraining programs. No serious conversation about what happens to entire categories of workers who find themselves obsolete.
We’ve seen technological disruption before—manufacturing automation, outsourcing, the shift from industrial to service economy. But those transitions played out over decades, and even then they were painful and left a lot of people behind. This AI transition feels like it’s happening in fast-forward, and we’re not prepared.
Should there be a tax on AI-driven productivity to fund retraining? Should companies be required to offer transition support to displaced workers? Should we be thinking about universal basic income or shortened work weeks? I don’t know, but the fact that we’re not even having these conversations in a serious way is part of what’s fueling the anxiety.
What This Means For You (And Me)
If you’re reading this and feeling anxious about your own job security, you’re not alone. If you’re wondering whether your skills are going to matter in five years, you’re asking the right questions.
The honest answer is that nobody knows exactly how this plays out. But here’s what I do know: adaptability is going to matter more than it ever has. Being willing to learn, to evolve, to get uncomfortable—that’s not optional anymore.
I also think there’s real value in focusing on the parts of your job that require judgment, creativity, relationship-building, and emotional intelligence. Those are still hard for AI to replicate. Not impossible, but hard. And in a world where AI can do the technical analysis in seconds, being the person who can read the room, understand the politics, build trust, and make the judgment call becomes more valuable, not less.
What Now?
We’re watching something historic unfold in real time. The way we work is changing faster than most of us ever expected, and the anxiety that comes with that is completely understandable.
Companies like Block and Citi are just the latest in what’s going to be a long line of organizations reshaping themselves around AI. More are coming. Many more.
The question isn’t whether AI is going to change the employment landscape—it already is. The question is whether we’re going to manage that transition in a way that doesn’t leave millions of people behind. Right now, I’m not sure we have an answer to that. And that uncertainty? That’s what’s really keeping people up at night.
What’s your take on AI and job security? Are you seeing this play out in your industry? I’d love to hear your perspective in the comments below.
Disclaimer: This article is for informational purposes only and does not constitute financial or investment advice. Consult with a qualified financial advisor or tax professional before making any decisions about your investments or retirement accounts.
Jay Sadio, MBA
