07/20/2026
We've all heard it: fool me once, shame on you. Fool me twice, shame on me.
It gets tossed around like a warning label: don't be the person who gets burned the same way twice.
In coaching work, I've come to see it differently. It's not really about blame. It's about information.
When someone lets us down the first time, that's data. It might be a one-off, a bad day, a genuine misstep from someone who's otherwise reliable. We don't know yet. So we watch.
The second time it happens, we know something we didn't before: this is a pattern, not an accident. The misstep isn't in trusting someone again. It's in ignoring evidence we already have.
This shows up constantly in career and leadership work.
The colleague who keeps missing deadlines and blaming circumstances. The business partner who keeps "forgetting" agreements or boundaries. Friends or family not honouring our boundaries. The organization that promises change after change and delivers the same old processes or culture.
Giving someone a second chance isn't naive. Calling it faith when it's really something else is what gets us in trouble. Fear of conflict. Hope standing in for evidence. Not wanting to admit the first read was right.
The real skill isn't refusing to trust again. It's knowing the difference between a mistake and a pattern, and being honest with ourselves about which one we're looking at.
That takes self-trust as much as seeing others for who they've told us they are.
It means trusting our own observations, even when we'd rather not believe them.
Next time you're deciding whether to extend trust again, ask yourself one question: am I responding to who this person is, or to whom I hoped they'd be?
What's your experience with giving second chances? Earned, or not?
