Notes to my Imposter Self

Below are some notes I took after a conference. Reading them again, I am grateful I took the time to capture the feeling of being insufficient and discovering that I am good enough.

One of the root struggles I will have my whole life long is feeling good enough. Some of this is the cost of ambition, some of this is childhood work, and some of it just not having worked through my own value. I’m grateful that I have people in my life now who make me feel wanted and needed and valuable, just as I am, but I hope someday to treat these feelings of inadequacy with better consistency.

I’m posting these notes because they are both a good reminder to myself, and because one of the things about the online world is that it’s often polished. This blog is not polished and isn’t supposed to be. I write about my goals, my failures, my struggles and successes here, and I do it in my name because it’s honest and congruent with who I want to be and who I am.


I just finished the SAFe Summit in Nashville and among many other take always, I left the conference full of ambition and optimism and a profound sense of competency.

I’ve spent most of my career in highly bureaucratic, hierarchal organizations and I’ve honestly always felt like I never fit in. Early in my career, I thought it was just that I didn’t know anything at all. Later on, I learned that one of my great skills was in breaking the social rules just enough to find myself in conversations that were “above” my level. Finding a way to get an invite to a meeting with the most senior leader, getting onto projects that had “secret” funding, or telling my team “let’s just go talk with that leader” and showing up at their door became my set of magic moves.

But this always felt like I was the oddball out, not meant to be in those settings where following the rules and staying in your lane was rewarded with clear tokens, while I was busy gathering up “influence tokens” which were hard to cash out and hard to justify.

Going to this Summit, I got to see what all those years in the trenches had done to me: I’m great at talking to people about the real problems they are having in their business and recommending the way forward.

So many other people are stuck in the same traps I’ve seen and circumnavigated before. It’s always a problem of leadership buy-in, or cultural resistance, or not having the funding for transformation. It’s always an issue of not having the architecture and the roadmap. It’s always an issue of lip-service champions and mismatched leadership incentives. I’ve seen these problems and I’ve solved them before in some of the most entrenched environments we’ve created.

A colleague asked me “How do you tell people about our company?” And I took a second and said, “I usually don’t sell that way at all. No one wants to hear about how we’re a digital transformation company, or how we do advising. They don’t care about us. They want a problem solved. So I usually ask instead, ‘what’s the problem you are trying to solve?’ And that’s enough to get us moving in the conversation. If there’s a good fit, I tell them how we help solve those problems. If there isn’t, I recommend a course of action, but cut them loose soon so they can find a better company that can help.”

It feels so natural to me to draw a picture to describe the problem for a potential client, feels natural to me to ask compelling, scalpel-like questions that get to the heart of the matter. It feels obvious to me that we have to get in the room and tell leaders what will be expected of them and how their world is about to change. I just *know* the way forward and how to map the territory to get there.

The key lesson from this week: none of that is obvious and none of that is natural to other folks.

What feels easy, what feels intuitive, what feels simple, is exactly the stuff I should be honed in on. Where it feels hard, or gritty, or full of friction and resistance, avoid it. Now is the time for me to push hard at the things I’m good at, and recognizably good at, and to delegate and discard the stuff I’m not as good at. Play to my strengths and win.