7 Key Takeaways from My Post-CEO Sabbatical: What I'm Really Doing Now

Stepping down as CEO of Stack Overflow after a decade wasn't easy, but it opened up a world of discovery. In this listicle, I share seven insights from my ongoing sabbatical—how I'm spending my time, what I've learned about myself and the companies I lead, and why letting go has been the best decision for everyone involved. From working with a new CEO to exploring simulation software, here's what's keeping me busy.

1. The Sabbatical Mindset

After handing the CEO reins to Prashanth Chandrasekar, I've embraced a sabbatical—not retirement. It's a subtle but important distinction. I still join customer calls and meet weekly with Prashanth, but my schedule has opened up dramatically. More importantly, I'm discovering how little I truly knew about running a mid-sized company. Watching Prashanth reorganize everything for the better is oddly satisfying. The ultimate validation would be if he proves I was a subpar CEO by excelling—that's the best outcome for everyone.

2. Living in a NORC (But Not Retired)

Manhattan's Upper West Side is a Naturally Occurring Retirement Community (NORC), yet I'm anything but retired. I'm busier than ever, which is why I'm writing this update for readers who keep asking what I'm doing. The sabbatical label gives me permission to explore without the pressures of a full-time role, but the days are packed with board meetings, strategic planning, and new projects. It's a phase of learning and reflection, not rocking chairs.

3. A Furry Mascot Opportunity

Meet Cooper, my two-year-old dog. He's adorable and available for mascot duty—if your web app needs a lovable face, apply within! Beyond the lighthearted offer, Cooper represents the joy of slowing down. Taking him for walks forces me to disconnect and think creatively. Sometimes the best ideas come when you're not staring at a screen.

4. Chairman of Three Companies

I serve as chairman for three companies: Stack Overflow, Glitch (formerly Fog Creek Software), and HASH. Each operates in a different space, but they share a common thread—helping people build things. From developer Q&A to simplified coding environments to simulation platforms, these firms are pushing boundaries. My role involves guidance, not day-to-day management, which leaves room for high-level strategy.

5. Stack Overflow's New Chapter

Stack Overflow is in excellent hands with Prashanth. I won't rehash its well-known story here, but the platform continues to serve millions of developers. My involvement has shifted to advisory, which feels right. The community-driven model is strong, and I'm excited to see how it evolves under new leadership without my interference.

6. Glitch: Simpler Coding for Everyone

Fog Creek Software rebranded as Glitch, now under CEO Anil Dash. It's a friendly community for building the web, and it has grown to host millions of apps. We raised a solid funding round to accelerate growth. My belief: every era needs a simplified programming environment for developers who don't need git branches or multi-step deployment—they just want to write code and run it. Glitch serves that quiet majority perfectly.

7. HASH: Simulating the World

HASH remains mostly under the radar, but its website now reveals its mission: an open-source platform for agent-based simulations. Imagine modeling traffic as a city planner. Instead of assuming each bus removes 50 cars, you simulate each commuter's decision based on time and cost savings. HASH lets you test millions of bus routes computationally to find real traffic reducers. This approach works when closed-form formulas fail. It's powerful for complex systems like epidemiology, economics, and urban planning.

My sabbatical has been a whirlwind of discovery. Whether mentoring CEOs, playing with simulations, or walking Cooper, I'm learning that stepping aside doesn't mean stepping away—it means stepping into new challenges. And that's exactly how I want to spend this chapter.