We've Seen This Movie Before

During the pandemic, I was doing some equity analysis work, thinking about long-term tech plays. And it hit me that the entire world was being forced into remote work overnight. Managers had no choice. I thought, okay, this is actually a huge opportunity. If companies can figure out how to operate remotely, the benefits are massive — lower real estate costs, happier workers, access to global talent. The companies that mastered remote work would have a serious competitive advantage.

But here's what I didn't see coming: nobody actually knows how to do remote work well. Not the big players anyway. There's too much institutional inertia baked in. Good managers who thrived in person didn't automatically become good remote managers. And frankly, we weren't forced to stay remote long enough to actually figure it out. In December 2020, Upwork was forecasting that 36.2 million Americans would be working remotely by 2025 — an 87% increase from pre-pandemic levels. It didn't happen like that.

Now I'm seeing the exact same playbook with AI. Anthropic CEO Dario Amodei has been sounding the alarm loudly. In a May 2025 interview with Axios, he said:

"We, as the producers of this technology, have a duty and an obligation to be honest about what is coming... It's going to happen in a small amount of time — as little as a couple of years or less."

He's since doubled down, repeating his prediction that AI will wipe out half of all entry-level white-collar jobs within five years. And he's not alone — Andrew Yang, Sam Altman, Elon Musk, and a whole ecosystem of influencers are echoing the same urgent timelines.

Meanwhile, VPs across the country are signing massive enterprise contracts and begging employees to integrate AI into their workflows. But anecdotally, everyone I talk to who isn't directly working with models just shrugs. They don't see the benefit yet. And I don't think that's because they're lazy or resistant — it's because real organizational change doesn't work on a two-year timeline. It can't be mandated from the top. It requires new types of workers, new skills, and deep integration at every level of the org chart. You can't just buy a Copilot enterprise license and expect transformation to happen.

People and systems — especially large ones — are inherently rigid. It takes enormous courage to blow up the way you've always operated, even when the benefits of change are obvious. We watched that play out with remote work in real time. The technology was there. The incentives were there. The mandate was literally forced on every company on earth. And it still didn't stick the way the optimists predicted.

Remote work should have taught us this. The timelines being promised for AI? They're not going to happen like that.