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Michael Greenspan · July 20, 2026
After the Next One
Relief isn't at the next milestone
Michael Greenspan · July 20, 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 lot of the engineering leaders I coach are living on a promise they keep making to themselves.
Once we ship this. Once I backfill the role. Once the funding arrives. Then it’ll ease up.
You’ve made that promise for three milestones now. Each one bought a few days of relief before the next rung showed up. The calm you’re working toward stays one step ahead.
A few questions to ponder:
- What are you telling yourself will let up after the next milestone?
- Have the last few actually changed the feeling, or just reset it?
- What are you postponing until things settle, that settling was never going to deliver?
The reframe: You’ve been asking too much of the next milestone. The calm isn’t waiting there.
Have a great week!
— 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.