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The Hardest Resignation Letter You'll Ever Write
Sometimes founders and long-tenured leaders want to stay for the wrong reasons: they don't know what to do next, they haven't planned for their retirement, their identity is with the organization, or they don't think the organization can survive without them.

TrudyS
May 259 min read


Can We Offer Each Other a Little More Grace?
Never publicly shame anyone — this approach leads to resentment, damaged morale, and a workplace culture headed toward toxicity. That's not a culture any of us wants to build — especially not in mission-driven organizations where trust and psychological safety are foundational. Time for grace.

TrudyS
May 45 min read


Are We Paying Consultants to Tell Us What We Already Know?
I'm not here to argue that outside expertise is always theater. It genuinely isn't. And after years of watching organizations navigate this, I'd say there are some situations where the outside voice isn't just useful — it's the honest choice.

TrudyS
Apr 2015 min read


Damned If You Do, Damned If You Don't: The Impossible Tightrope of Letting People Learn
One of the most disorienting things about accumulating genuine expertise is that it can start to feel like a liability.

TrudyS
Apr 612 min read


You've Lost Your Mojo. Now What?
Writing this wasn't just an exercise in sharing wisdom — it was me working through my own reckoning out loud, because that's the only way I know how to do hard things.

TrudyS
Apr 28 min read
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