From CEO to Chairman: 10 Insights on My First Months of Semi-Retirement

After stepping down as CEO of Stack Overflow, I’ve embarked on a new phase that’s part sabbatical, part retirement, and entirely busier than I expected. Here’s a list of 10 things I’ve learned—and loved—about this transition, from being replaced by a better CEO to chairing three companies.

1. The Joy of Being Replaced

Watching Prashanth Chandrasekar take over as CEO has been oddly satisfying. It turns out I didn’t know as much about running medium-sized companies as I thought. He’s rearranging everything for the better, and the best outcome for me is if he proves what a bad CEO I was by doing a fantastic job. Freedom from daily operations gives me time to reflect—and marvel at how much I missed.

2. Sabbatical vs. Retirement – A Mindset Shift

Even though I live in what’s jokingly called Manhattan’s premier NORC (Naturally Occurring Retirement Community), I prefer calling this a sabbatical. Retirement sounds too final; a sabbatical suggests I’ll return to something new. And I’m anything but idle—I’m constantly learning, advising, and building. This mental framing keeps me engaged and open to opportunities.

3. Living in Manhattan’s Premier NORC

Our building is full of retired professors, artists, and tech folks—a natural retirement community. It’s a wonderful place to be, with built-in social circles and intellectual stimulation. But I’m not ready to settle into full retirement; the NORC vibe is more like a supportive backdrop for my ongoing projects.

4. Cooper the Dog – The Office Mascot?

Meet Cooper, our two-year-old pup. He’s adorable and keeps me company during work hours. If your web app needs a mascot, apply within—he’s available for virtual appearances. He reminds me that life after the C-suite should include small joys and furry distractions.

5. Chairman of Three Companies – A Different Kind of Busy

I’m now chairman of Stack Overflow, Glitch (formerly Fog Creek Software), and HASH. Each role is vastly different: at Stack Overflow, I mentor leadership; at Glitch, I help shape community growth; at HASH, I dive into simulation platform strategy. It’s busy, but the variety keeps me stimulated without the day-to-day grind.

6. Stack Overflow – Still Close to My Heart

Of course, Stack Overflow remains my baby, but now I’m on the sidelines. I still join customer calls and meet weekly with Prashanth. It’s fascinating to see how the platform evolves without my constant input, and I’m learning to let go. The company is in great hands.

7. Glitch – The Friendly Community for Building the Web

Glitch (formerly Fog Creek) has grown into a vibrant community. CEO Anil Dash has led the team to millions of apps and a solid funding round. The idea is simple: a simplified programming environment for the majority of developers who don’t need advanced features like git branches—just write code and run it. It’s the democratization of coding.

8. The Evolution of Fog Creek Software to Glitch

Fog Creek Software, which I founded, has been reborn as Glitch. The name change reflects the shift from a tools company to a community platform. Under Anil, the focus is on making web development accessible. I’m proud to see it become a haven for hobbyists and pros alike.

9. HASH – An Open Source Platform for Simulations

HASH is my newest venture, still flying under the radar—but today they put up a whole bunch of words on their website, so I can share a preview. HASH is building an open source platform for simulations, specifically agent-based modeling. Think of modeling traffic, epidemiology, or market dynamics by simulating individual agents.

10. Why Agent-Based Modeling Matters

Agent-based modeling is powerful because it works when closed-form formulas fail. For example, a city planner simulating a new bus line can model each commuter’s decision-making. HASH lets you run millions of scenarios to see what actually reduces traffic. It’s computationally intensive but incredibly insightful for complex systems.

This semi-retirement has taught me that letting go opens up new worlds. From watching a new CEO thrive to championing simulation software, I’m busier and happier than ever. The key is staying curious, staying engaged, and sometimes just playing with your dog.