Prove Yourself, Prove Yourself Again
Your work can't make you feel safe
Michael Greenspan · July 27, 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.
Something that comes up often, especially after a reorg or a promotion, is the pressure to keep showing you’re worth keeping. You shipped the migration, hit the date, and for about a week it felt settled. But then the next sprint starts and the quiet question comes back: what have I done lately? Prove it again. And again.
A few questions to ponder:
- Where are you working to prove you’re needed rather than to do the work itself?
- Who are you proving it to, and have they actually asked?
- What needs to be true in order for you to finally feel like you’ve actually “proved it”?
- What gets neglected when you are more focused on proving your worth than getting the job done?
The reframe: The validation that comes only when you prove yourself never quite stays. You’ve been asking your output to make you feel safe. It can’t. I can’t tell you what can. It’s personal. But it may be worth further reflection.
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.