Surviving the AI Grind: Token Junkies, Hustle Culture, and Stressed-Out Leaders w/ Eric Weber

The Weekend Windup #27 - Cool reads, events, links, and more

If you’ve been paying attention to the tech scene (especially in San Francisco), you’ve probably noticed a distinct vibe shift lately.

Last week, I took a stroll through downtown SF with my friend Eric Weber. While we didn’t overhear many overt conversations about AI on the street at 8 am, it was definitely the elephant in the room in our own chat and in broader conversations with friends in the city.

The reality on the ground is stark, awesome, and scary. Since 2022, the tech industry has been grappling with waves of layoffs. Then AI took off (again), and although it sucked for a while, it got really good in 2025. As far as I can tell, it’s only improving. A friend who very instrumental in spurring this latest AI revolution told me, “2026 is going to be wild.” Meaning, the capabilities of the models are blowing the minds of even the people smack dab on the middle of building what’s next. But for all the public cheering about the “AI revolution,” there is a very real, palpable fear creeping into the ranks of tech workers and leaders alike.

Every Week is a New Year

In the tech industry, we are used to change. In places like the Bay Area, change is practically the regional ethos. But what we’re experiencing right now is different. I remember the Lean Startup revolution of the 2010s, and I thought the pace of change back then was fast. “Everyday I’m hustlin’” was the soundtrack of a generation. That time was cute and quaint, like a 1950’s TV show. In 2026, that ain’t shit. In 2027, our speed won’t be shit either. We aren’t just adapting to a new framework or a shifting business model over a series of years, nor spending years graduating to a new funding round. If you’re not growing to a few million in ARR within the first year (or soon to be a few months), you might as well GTFO. I’m probably not being extreme enough, but whatever. You get the idea. Things - and the things that make things - are moving faster and faster. “Every nano-second I’m hustlin’” is the new song for AI agents.

The toll is real on practitioners and leaders. Especially if they’ve been around for a while, people have these heavy, grounding moments when the task they are best at - the thing that previously took them a week of deep work - suddenly gets done by a model in 30 minutes. It’s disorienting. It’s causing a massive identity crisis. People are genuinely asking: What does it mean to be a professional right now? Will my skill set even be valued next year?

Very good question, and I don’t sense anybody has an answer right now. We’re living through whatever the people in the Industrial Revolution went through (we even have our own Gilded Age), yet moving at a speed that’s absolutely jarring, no matter who you are. The platitudes that people are going to “find new things to do, since that’s what’s always happened” fall flat when the pace of change is at warp speed. It took years and decades to build railways, steam engines, electric grids, the Internet, and other things that transformed society in the past. Nowadays, we’d wish for such a glacial state of change, since that would at least give us breathing room to adapt. But we’re moving too fast. Even people I know at the cutting edge of AI are struggling to keep up. Indeed, every week seems like a new year.

The Dawn of Reverse Centaurs and Token Junkies

This brings us to the darkest part of the conversation. We often hear about the “Centaur” model of AI, where the machine boosts human capability, making us faster and better.

But what happens when it goes the other way? What happens when humans just become cogs in the AI machine?

Cory Doctorow and I chatted on my podcast about his idea of the Reverse Centaur. As he says in an article in Locus, “There’s a bit of automation theory jargon that I ab­solutely adore: “centaurs” and “reverse-centaurs.” A centaur is a human being who is assisted by a machine that does some onerous task (like transcribing 40 hours of podcasts). A reverse-centaur is a machine that is assisted by a human being, who is expected to work at the machine’s pace.”

We’ve seen this play out in Amazon warehouses, where human motion is dictated entirely by an algorithm, optimizing output to the point of dehumanization. Sadly, with everyone using AI coding and productivity tools, we are dangerously close to bringing that exact dynamic to white-collar work. When you have executives essentially viewing employees as token-consumption engines, the humanity gets stripped away. If productivity is measured solely by how many tokens you burn through rather than the judgment you apply, and how much “stuff” you’re cranking out, we are just building a digital sweatshop.

The difference between past sweatshops and the digital one we’re about to enter is that we’re happily giving the sweatshop feedback on how to do our jobs. I use AI as much as the next token junkie. But I have concerns, as I’m sure you do. AI saves us time in the short run, but I’m curious whether we’ll regret it later. But the token crack pipe is too nice a rush to put down, so we continue taking another hit. As Ministry once shrieked, “Just One Fix.”

The Leadership Squeeze

If you think the individual contributors are stressed, the leaders are at their breaking point. They used to manage craftsmen. Now that the very nature of craftsmanship is being questioned (as it was in the Industrial Age), what exactly is expected of leaders? As Eric points out, good leadership requires wearing three distinct hats:

1. The Company Hat: Protecting financials and driving growth.

2. The Technology Hat: Navigating this insane pace of technical change.

3. The People Hat: Caring for a team that is deeply anxious about their livelihoods.

Right now, all three of those domains are shifting simultaneously. Leaders are standing at the epicenter of that earthquake, trying to hold it all together while fielding directives from the top that often sound completely detached from human reality.

Of course, what is a leader in the future, say one to two years from now? Some people predict a collapse of knowledge work by 2030. Others think that the nature of hierarchies and their managers changes dramatically. So, leaders are taking it from all angles, trying to appease their various stakeholders, stay on top of wave after wave of technology, all while asking themselves, “Why am I in tech?” I’ve met quite a few leaders who want to leave the tech industry and pursue more meaningful, less stressful hobbies like gardening, ranching, or traveling.

Stepping Back

As Eric says, if you’re going to hustle, the compensation better be worth it. Especially now. This environment is a big reason why Eric recently stepped back from his leadership role. When the hustle demands everything, but the compensation no longer feels worth the existential dread, something has to give.

For Eric, the antidote has been writing and leaning heavily into real, human connection - spending time on coffee walks, listening to people, and realizing that folks just want to know they aren’t alone in this.

I tend to agree. The models will keep getting faster, and the tech will keep shifting. But bad advice and sweeping generalizations won’t save us. Grounding ourselves in the real world and talking through the actual, unglamorous realities of this transition will.

Are you a token junkie? Do you lead token junkies? Curious how you’re handling the changes that are happening right now. Drop them in the comments.

Have a great weekend,

Joe

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Awesome Upcoming Events

Here are a couple of things I’m up to. Travel calendar is in the works (it looks insane), so stay tuned.

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Agentic Analytics Summit 2026

AI + agents is what’s happening right now. I’m speaking at Agentic Analytics Summit on April 29th. More details to follow soon, but feel free to register for the event here.

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Data Innovation Summit 2026 - Nordics

🇸🇪 Sweden! See you at the Data Innovation Summit in Stockholm.

I’m doing a keynote and workshop on Mixed Model Arts: Data Modeling in the Age of AI.

• May 7 - keynote

• May 8 - workshop

Here’s 10% off: SD10OFF (good for the event. Workshop is not included)

Register here

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Cool Videos and Reads

Why You’re Losing 90% of Your Data (And How AI Fixes It) w/ Amit Prakash

Are traditional CRMs on their way out? In this episode, Amit Prakash (CEO of Ampub and ThoughtSpot co-founder) drops a massive truth bomb: forcing messy, high-dimensional reality into structured tables destroys 90% of your data's value.We dive deep into the looming "SaaS-pocalypse" and why the future of enterprise software belongs to unstructured data. Amit breaks down how AI buying and selling agents will soon handle the tedious "dating dance" of early negotiations.

If you're wondering where the actual ROI in AI is hiding, Amit argues that fixing the sales bottleneck is the ultimate unlock for technological innovation and global GDP. We also explore dynamic ontologies, and the inevitable rise of a centralized "Business Brain".

Breaking Into Data Engineering in 2026: Standout Resumes, Career Changes, and more w/ Chris Gambill

In this episode, I sit down with Chris Gambill, a data strategy and engineering leader, fractional consultant, and career coach. We dive into the realities of the data engineering job market in 2026, exploring what it takes to stand out, the massive shift AI coding tools are causing, and why mastering the fundamentals of data engineering remains crucial.

Chris shares his unfiltered thoughts on coaching career switchers into data engineering , why finance professionals make great data engineers , and the exact resume and portfolio strategies hiring managers are actually looking for. We also get into the weeds on the latest AI development tools, comparing GitHub Copilot, Claude, and Codex.

If you're looking for solid, no BS advice on the field of data engineering in 2026, this is a great discussion!

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Here are some things I read this week that you might enjoy.

Employees Are Taking Pay Cuts in Huge Numbers - Business Insider

Opinion | I Saw Something New in San Francisco

Educated and employed but still struggling: India’s middle class under strain

He Helped Stop Iran from Getting the Bomb | The New Yorker

AI Enablement Engineer: The Highest-Leverage Role in Tech | Preset

Forecasting the Economic Effects of AI

The Big Business Intelligence Squeeze - by Darragh Murray

Economists Are Drawing Stronger Connections Between A.I. and Jobs - The New York Times

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