The edge is supposed to feel like this
Last fall I lost a sizable contract. Real revenue, real cash flow impact, real runway concern.
I had clients I trusted. Long relationships. A degree of professional courtesy that had built up over time. And I needed to ask one of them to pay me early.
I didn't ask. Not right away.
I was afraid of the version of me they might see if I made the ask. Someone who needed the money. Someone performing stability they didn't actually have. I was protecting a façade — and the protection was costing me days of cash flow I couldn't afford to lose.
I want to be clear about who I am when I tell you this story. I'm a confident person. Capable, high-performing, focused. I know my place in things. I've worked hard to earn it. And I can still walk straight into that imposter dynamic — that feeling that if someone looks a little closer, the gap between who I appear to be and who I actually am in this moment will become visible.
I'd guess some of you know exactly what I mean.
For people like us — people who hold it together for others, who show up convincing, capable, whole — that dynamic can feel like a private failure. Like evidence of something we're hiding. I'm growing increasingly convinced that the only people who never experience this are sociopaths and narcissists. For the rest of us, it's edgy, clumsy, sometimes naked — and it means we're doing something real.
The imposter dynamic shows up at the edge. It's what high performance feels like when it's actually working — when we're operating at the boundary where comfort meets something new, something difficult, something not yet fully mastered. Coasting never produces that feeling. Safe doesn't either. That feeling is pointing to something worth paying attention to: we're evolving, we're out where it counts.
Sometimes we wish someone else could make the hard call. Sometimes we wish the uncomfortable email didn't have to be sent, or that circumstances would just resolve it for us. When we hand that moment off — to delay, to someone else, to waiting for more data — we're withholding from ourselves the one thing that actually closes the gap: the experience of doing the hard thing and discovering what comes next.
I finally sat down in a booth at a burger place one afternoon in September, eating chicken tenders, and deliberated over the language in an email longer than I'd like to admit. Then I hit send.
What came back was respect. Accommodation. No shift in the relationship at all.
And the moment I hit send, I could move on to the next thing.
I never thought that email — over chicken tenders, on a sunny afternoon — would be the thing I'd be writing about here. But it is. And I'm glad it happened to me.
If this makes you feel a little silly, or maybe a little embarrassed — there's probably something to it.
That's exactly what I'm experiencing right now.
About Dave
Dave O'Connor is an executive coach based in Market Square, Lake Forest, Illinois, who works with senior leaders in person and virtually. He holds the ICF PCC credential and is a former president of a private equity-owned company. He coaches founders, CEOs and owners on personnel, product, partner and positioning decisions.
Dave O'Connor, Executive Coach · 253 Market Sq Ste C, Lake Forest, IL 60045 · 518-727-6531 · Mon-Fri 9am-5pm