The Expertise Trap — Issue #04
If You Can't Imagine Doing Anything Else, That's the Trap — 4 Questions to Find Your Way Out
ONE STORY, ONE SIGNAL, ONE TOOL, ONE QUESTION - EVERY WEEK
Issue # 04 - The Expertise Trap
There is a question I ask most mid-career clients at some point in our work together. “Tell me what you want next.”
The answers follow a familiar pattern.
More scope. A stronger team. A title that finally matches the responsibility they’ve been carrying for years. Higher pay, a better organization, a manager who actually sees them.
None of those things are wrong to want. But when every option someone can generate is a variation on the same theme, when a bigger version of the job they already have is the only path they can picture, that pattern is worth a closer look.
This issue is about that pattern.
A Coaching Story
💬 A de-identified composite scenario based on my coaching experiences. This story does not reflect the experience of any particular individual or organization in any way.
He had been in his field for fifteen years. Senior director at a well-regarded company, the person his team called when something complicated landed on their desk. His performance reviews used words like “indispensable.” His manager had told him, more than once, that he was being considered for the next level of leadership.
He came to coaching not because anything was acutely wrong. He had the nagging sense that he wasn’t going anywhere, and he couldn’t explain why. “Stuck” was the word he kept using.
When I asked what he wanted next, he didn’t hesitate. “Something bigger with more scope. A VP role, ideally. I’ve been doing the work for a while.”
“Okay,” I said. “What else?”
He looked at me. “What do you mean, what else?”
“If the VP role doesn’t materialize, if the timing is off, or the organization isn’t moving that direction, what else are you considering?”
The pause lasted long enough that I let it sit.
“I guess,” he said finally, “I’d look for this same kind of role somewhere else. Somewhere better.”
That was where his real work started.
He wasn’t wrong to want a VP role, he may well have earned one. But every path he could picture was a variation on the one he was already on. Fifteen years of deep expertise had become the only lens he could see through. That was the trap. Not the job, not the organization. The trap was the narrowness of what he could imagine next.
A few sessions later, I walked him through a diagnostic I call the Four E’s, four questions about what any role is actually giving you. We went through each one. His silences got longer as we went.
When we got to the last question, he said, “I’ll be honest: that one’s been missing for a long time.”
Once he could name which E had gone flat, what to do next became much clearer. The answer wasn’t a job search, not yet. He just needed one targeted move to start replenishing what had quietly run dry. It was a smaller step than he expected, and more clarifying than two years of feeling stuck.
The Changing World of Work
📊 A key data point and my insights about what it means to the changing world of work around us.
A Harvard Business Review analysis from February 2026 found that AI is not reducing the cognitive load on knowledge workers, it is intensifying it. The expertise mid-career professionals have spent years developing is being both replicated and accelerated by the same tools, at the same time. Harvard Business Review, “AI Doesn’t Reduce Work — It Intensifies It,” February 2026
There is a counterintuitive finding buried in recent McKinsey research worth sitting with: heavy AI users report the highest intent to quit of any group of workers. The most capable knowledge workers, the ones who adopted AI earliest, are the most likely to be looking for a way out.
What the data shows is more specific: AI is hitting hardest at professionals who built careers on deep expertise, knowledge workers whose entire identity is tied to cognitive work they spent decades developing. When a tool starts doing the thinking you’re known for, the question isn’t whether your expertise still has value. It’s whether you’ve been growing in all four dimensions of your work, or deepening just one while the other three went quiet.
McKinsey & Company, “How AI is — and isn’t — changing the future of work,” 2026
This Week’s Resource
⚙️ A framework, tool, tip, AI prompt or skill that you can save and put to use immediately.
The Four E’s: A Diagnostic for What Your Career Is Actually Giving You
I developed this framework for my book Professional Careers By Design, and I use it with coaching clients when someone knows something is off but can’t name what. Think of it as a diagnostic, not a test of whether to stay or go. It’s four questions about what your current role is actually giving you right now, and what it isn’t.
Education. Are you actively learning something genuinely new? Not just getting better at what you already know, but encountering new skills, new ideas, new ways of thinking.
Experience. Are you building experience in new contexts, a new kind of challenge, a new level of leadership, a new type of organization? Or are you accumulating more of what you’ve already mastered?
Exposure. Are you being seen by people outside your current circle, stakeholders, peers or leaders who could open doors you don’t currently have access to?
Enthusiasm. Is there still a part of your work that lights you up and that carries genuine meaning beyond the deliverable?
With clients, I ask them to go through each question in the context of their current role. What’s actually true today, not what they wish were true.
In my experience, one or two E’s have gone quiet for clients at this stage. Gradually, in a way that’s easy to rationalize, and even to miss. That depleted dimension becomes your very next action. It doesn’t have to be a new job search, just one targeted shift. A new learning commitment, a new context, a new relationship, a project that reminds you what enthusiasm feels like.
What you can steal from this: my client from the story above knew within minutes which E had been flat for two years. It was enthusiasm. Naming it was more clarifying than anything else he’d tried. And he was stunned at how easy it was to regain that sense of joy with just a small shift. He asked to be part of a new team forming to assess the role of AI in their company, and he became the voice of senior folks there who were interested, not skeptical. His voice was valued, he learned new AI skills and became visible doing so. And his joy returned. He eventually stayed with that company and evolved that team assignment into a new role for himself outside the lane he had been imagining.
🔻 The full Four E’s worksheet — the same tool I use with coaching clients — is available as a free download here. It takes about 15 minutes to complete and most people find it uncomfortably useful. 🔻
A Powerful Coaching Question
🤔 This week’s high-value coaching question for you to consider in whatever way you like to reflect.
Which of the four E's has been missing the longest for you? New learning, new experience, new visibility or genuine enthusiasm? And what have you been telling yourself about the reason for that?
Inspiration for the Week
“The only way to make sense out of change is to plunge into it, move with it, and join the dance.”
— Alan Watts
The trap isn’t expertise. Expertise is real and earned and worth protecting. The trap is deciding that because you know what you’re good at, you no longer need to ask where you’re growing. The Four E’s aren’t a one-time inventory. They’re a practice, and mid-career professionals are exactly the ones most likely to stop practicing those questions at the moment they need them most.
Before You Go
Run through the four questions this week. Then reply and tell me which E came up empty. You don’t need the full answer yet about what to do next. Just name what’s missing.
That’s where your next chapter starts.
Until next week,
Did you do the Four E's questions for yourself? Leave a comment about what you learned!