You had a plan.
You'd spend another year proving yourself. Hit a few more targets. Build the case so thoroughly that when the moment came, there'd be no question — not from them, and not from you.
And then the moment came early. And instead of celebrating, your first thought was: do I really deserve this?
One marketing leader we spoke to this season had mapped out her exact path to CMO. She'd been hired as VP of Marketing, she knew what she needed to prove, and she'd given herself a reasonable timeline to prove it.
Six months later, they made her a CMO.
"Do I really deserve that? Do I really deserve that?"
It's a kind of vertigo a lot of high-achieving leaders will recognize. You work toward something, build a very logical case for why you'll earn it eventually — and then it arrives before the case is complete. Before you've checked all the boxes you invented for yourself.
And rather than celebrating, you question.
The plan was your security. The timeline was your proof. Without it, the achievement feels accidental.
Here's what she learned in those early months: The role wasn't a mistake. The organization saw what she hadn't yet let herself see — that she was doing exactly what she was built to do. And when she finally stopped waiting for permission to feel worthy of it, she started doing her best work.
"I stopped allowing myself to shrink."
If you've been waiting for the right moment to feel ready — maybe the opportunity has already arrived. And maybe the only thing standing between you and it is the timeline you gave yourself that no longer applies.
This email was inspired by a recent conversation with Deidre Hudson on The Ripple podcast.
For many of us, the opportunity that’s arriving early is related to AI - and how we as leaders are approaching it. If that sounds like you - or someone you know - come join us for the newest Wednesday Women online event.
“Riding the Wave: Integrating AI at the Leadership Level” | May 27th, 2026 - an interactive, discussion-based panel exploring how leaders in different functions are stepping into AI leadership and making real impact.
*This event is brought to you by our partner Booth - who delivers high-performing talent, specialized skills, and AI-enabled support to help companies grow - without sacrificing quality, control, or culture.
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Every issue is written by hand, by one of our amazing Wednesday Women team. We encourage you to forward it to a friend or colleague who might appreciate the inspiration!
