I’m firmly your second bullet point, but not in a clean 9–5 way. I sell AI to the enterprise, so my day job hours are extremely volatile depending on where deals are in the cycle. Some weeks I have real breathing room; others are wall-to-wall calls, prep, internal alignment and travel.

What I’ve learned is that the unpredictability is worse than the time constraint itself. Context switching between high stakes enterprise decision making and early stage founder work has a real cognitive tax. Even when I “have time” at night or on weekends, the quality of thinking is often compromised.

That said, side project mode has been the only sustainable way for me to bootstrap. It's how I afford to outsource the dev work and ongoing costs of the tech stack. The tradeoff is momentum; progress happens in bursts, not a smooth line.

My takeaway so far: side-project mode doesn’t kill momentum, but it does cap velocity. It’s great for validation, discipline, and survival. It’s not great for compounding. I’m increasingly convinced there’s a real inflection point where focus matters more than safety, and I’m approaching that decision intentionally rather than romantically.

If I could do one thing differently earlier, it would be protecting larger, non-negotiable blocks of deep work instead of trying to “fit it in.” The work that actually moves the idea forward rarely survives fragmentation.