← More reflections Weekly reflection 
Michael Greenspan · June 22, 2026
The Decision You Keep Circling
Michael Greenspan · June 22, 2026 Monday mornings, I send you something short to sit with. Not advice or a framework, but a question, and some room to think it through yourself.
A situation a lot of engineering leaders find themselves in is being stuck on a decision. You’ve reopened it five times. And every day that goes by, the stakes become higher.
A few questions to ponder:
- What decision have you been moving to next week, week after week?
- Are you stuck on the decision, or stuck looking for the option that lets no one down?
- Are you waiting for certainty where certainty can never exist?
- If you trusted your own judgment fully, what would your decision be?
The reframe: What you’re waiting on isn’t more information, it’s a certainty a call like this will never give you. And holding it open isn’t staying safe. It’s just the slowest, most expensive way to decide.
No fix or homework, but something to chew on.
— Michael
These weekly reflections aren’t about doing more or fixing yourself. They’re a moment to slow things down and notice what’s actually going on. Because noticing is usually where the change starts.
P.S. These are yours to keep private. But if you’d like to think through this one together, just reply. I read every one.