It’s Happening Faster Than You Think
AI layoffs aren’t a future problem anymore. They’re today’s headline — and tomorrow’s new normal.
Two weeks ago, I wrote a piece called The Ladder Is Evaporating. In it, I argued that the career path that built the American middle class (get the degree, land the entry-level job, grab the first rung, start climbing) was breaking apart in real time. I said the first rung was already gone and the rest weren’t far behind.
I thought I was early. I wasn’t.
Today, Jack Dorsey announced that Block, the company behind Square, Cash App, and Afterpay, is cutting more than 4,000 employees. That’s nearly half its workforce, from over 10,000 to just under 6,000. The reason, in Dorsey’s own words: intelligence tools have changed what it means to build and run a company. A smaller team, using the tools they’re building, can do more and do it better. The stock didn’t crash. It soared, up more than 24% in after-hours trading. Wall Street didn’t see 4,000 people losing their livelihoods; it saw a company getting leaner, faster, and more profitable.
And Block isn’t even the only company making this move right now. DocuSign just announced layoffs reducing its workforce from over 10,000 to under 6,000 employees. Two major companies running the same playbook and arriving at the same math tells you everything you need to know about where this is heading.
The Dam Is Breaking
Block and DocuSign aren’t isolated cases. They’re the latest, and the largest, in a cascading series of companies explicitly linking workforce reductions to AI. Pinterest cut 15% of its workforce last month. Chegg eliminated 45% of its staff facing the “new realities of AI.” CrowdStrike, HP, Workday, and Salesforce are all on the list, and it keeps growing. Amazon has cut roughly 30,000 corporate roles since late 2025. U.S. companies announced over 108,000 layoffs in January alone, up 118% from a year ago, making it the highest January figure since 2009.
Fair-minded people will point out that some of this is “AI-washing.” Companies that overhired during the pandemic are using AI as a convenient narrative to frame cost cuts as forward-looking strategy. Block nearly tripled its headcount between 2019 and 2025. DocuSign ballooned during the remote-work boom. There’s a legitimate case that some of these layoffs have more to do with bloated org charts than genuine automation.
But here’s the truth: even if half of these announcements are overstated, the direction is unmistakable. When a CEO like Dorsey says a significantly smaller team can do more and do it better, and the market rewards him with a 24% pop, the incentive structure for every other CEO in America just shifted. Dorsey himself said it plainly: “Within the next year, I believe the majority of companies will reach the same conclusion and make similar structural changes.”
And make no mistake: while these headlines are currently centered around forward-looking tech companies, no industry will be spared. Every company that employs people who sit at desks and work on computers is running the same calculation, whether they’re in finance, insurance, law, healthcare administration, marketing, or manufacturing management. Tech is simply where the wave is hitting first. It won’t be where it stops.
This Is What I Was Warning About
In The Ladder Is Evaporating, I wrote about seeing this from two vantage points: as the CEO of B:Side Capital, where the math of AI agents versus junior hires is becoming impossible to ignore, and as a professor at ASU, where I watch bright, capable students prepare for a world that may not exist by the time they graduate. Today’s news didn’t ease that dissonance. It sharpened it.
This isn’t a company trimming around the edges. This is a founder looking at his 10,000-person company and saying, publicly, that AI has made roughly half of those positions unnecessary, and DocuSign is making the same calculation independently. These moves give permission to every other executive who’s been running the same math quietly. The Overton window on AI layoffs just moved dramatically.
So what do you do? I’m not going to pretend there’s a simple answer, but I believe there’s a clear one. And it comes down to which side of this divide you’re on right now.
If You’re Currently in the Workforce
Your job is your most valuable asset. Protect it strategically. Your current position gives you something no amount of upskilling courses can replicate: a funded laboratory. You have a stable platform, a paycheck, and a live environment in which to learn the most consequential skills of your professional life. Your number one priority is to keep that position, not out of fear, but because it’s the smartest strategic move available to you.
Become the AI expert in your role. Every company in America is about to go through some version of what Block just went through. Most organizations are still in that awkward limbo where leadership knows AI is coming but rank-and-file adoption is patchy. That limbo is your window. The person who figures out how to use these tools to genuinely multiply their output doesn’t get automated; they become the person who leads the automation. Don’t wait for permission. Start now.
Get closer to the customer. The further you are from revenue, from the client relationship, from the sale, from the decision that generates real-world value, the more exposed you are. Back-office analytical work is the first to go. Client-facing, relationship-driven work is the most protected. Face-to-face matters. Relationships matter. AI can process information, but it cannot sit across from a human being and build trust.
Expand your scope. Take on new projects. Volunteer for cross-functional work. Be an intrapreneur, someone who operates with the initiative and ownership of a founder within the structure of an existing organization. When leadership looks around and asks “who understands this stuff?”, your name should be the first one that comes up.
If You’re a Student
The advice I give my students at ASU has changed dramatically in the last twelve months. The old playbook, the one built around polishing the résumé, prepping for behavioral interviews, and networking your way into an entry-level analyst role, was designed for a world that is disappearing.
Build your soft skills, and I mean really build them. AI can process information faster than any human who ever lived, but it cannot read the room. It cannot close a deal. It cannot look a client in the eye and know when to push and when to listen. Learn to sell. Learn to persuade. Be a people person, not because it’s a nice line on a résumé, but because it’s becoming one of the hardest skills to automate.
Learn a trade. This might sound counterintuitive coming from a business school professor, but hear me out. AI is extraordinary at tasks that live entirely on a screen. It is terrible at anything requiring physical presence, human trust, or navigating the chaos of the real world. Anything with a physical component, whether that’s construction management, skilled trades, healthcare, or logistics, will be harder to replace for a long time. Lean into the physical-digital gap.
Be an entrepreneur. AI can do the work, but it can’t get inspired. It can’t spot an opportunity in a conversation with a small business owner. It can’t feel the pull of an unmet need and decide to build something that addresses it. One person with the right AI tools can now do what used to take a team of ten. Find an opportunity and chase it. If the traditional ladder is evaporating, build your own.
Learn to implement AI in Main Street businesses. This is where I see one of the biggest opportunities for the next generation. There are millions of small and mid-sized businesses that know AI is coming but have no idea how to implement it. They don’t need a McKinsey engagement. They need someone who understands both the technology and the reality of running a business on Main Street, someone who can walk in, assess their operations, and help them adopt the tools that will keep them competitive. That person could be you.
The Obstacle Is the Way
The temptation right now is to freeze. To wait and see. To hope the predictions are overblown, that someone will step in and slow this down. I understand that impulse. But Dorsey isn’t waiting. DocuSign isn’t waiting. The market isn’t waiting. And the thousands of people who woke up this week with jobs and will soon be without them didn’t get a warning that the timeline was accelerating.
The worst thing you can do is pretend this isn’t happening. The second worst thing is to panic and assume all is lost. The people who thrive in disruption are the ones who move toward the change rather than away from it.
I said two weeks ago that the ladder is evaporating. Today’s news confirms it. The question isn’t whether the world of work is being rewritten, it’s whether you’ll be the one holding the pen or the one reading about it after the fact. Start moving now, move fast, and move toward the fire, because that’s where the opportunity is being forged.