When the Institution No Longer Fits

I have left a lot of rooms in my career.

Some of those exits were straightforward — a mandate completed, a natural transition point, a new opportunity that made the decision easy. But a few of them were harder. The kind where the role was still good, the compensation was still strong, and the people around you were still telling you that you were exactly where you should be.

Those are the exits that teach you something.

The Trap of the Well-Fitted Role

There is a particular kind of professional trap that catches high-performing executives more reliably than almost any other. It is not failure. It is not stagnation in the obvious sense. It is the trap of the role that fits well enough.

You are competent. You are respected. The work is meaningful in the ways that matter to the people around you. And yet something has shifted — quietly, gradually — and the person you are becoming no longer quite matches the container you are in.

This is not a crisis. It rarely announces itself dramatically. It tends to arrive as a low-grade restlessness. A sense that the problems you are solving, while real, are not quite the problems you are most equipped to address. A growing awareness that your best thinking is happening outside the building rather than inside it.

Most executives I have known — and I include my earlier self in this — respond to that restlessness by working harder. By finding new projects within the existing structure. By telling themselves that the feeling will pass once the current challenge is resolved.

Sometimes that is the right response. But sometimes it is avoidance dressed up as commitment.

What Enbridge Taught Me About Deregulation — and About Myself

In 1999, I joined Enbridge as Director of Business Development at a genuinely interesting moment. The Ontario energy market was being deregulated, and Enbridge was building the retail sales and service infrastructure to compete in that new landscape.

The work was complex, fast-moving, and consequential. I negotiated a $40 million annual contract for service delivery. I helped build the technology systems that would support a new kind of energy retail business. I was part of a senior management team that was, in many ways, inventing its own playbook.

And I learned something important during that period — not just about business development or contract negotiation, but about the relationship between institutional momentum and individual judgment.

Deregulation, at its core, is a story about what happens when the rules that structured an entire industry are rewritten. The organizations that navigate it well are the ones that can hold onto what is genuinely valuable from the old model while being ruthlessly honest about what needs to change. The ones that struggle are the ones that mistake the familiar for the essential.

I found myself thinking about that dynamic not just in relation to the energy market, but in relation to my own career. The question was not whether the institution was good. It was whether the institution was the right place for the next version of what I was trying to do.

The Decision to Step Outside

When I left the City of Edmonton in 2014 after five and a half years as CIO, I was stepping away from one of the most significant roles of my career. The work had been meaningful. The scale had been extraordinary. And there was more to do — there is always more to do in a role like that.

But I had also reached a point where I could see, with reasonable clarity, that the most valuable contribution I could make was no longer as an operator inside a single institution. It was as someone who could move between institutions — bringing the perspective of someone who had been inside the machine, without being constrained by any particular machine's logic.

That is a different kind of value. And it requires a different kind of courage to claim it.

The courage is not in the leaving. The leaving, once you have made the decision, is relatively straightforward. The courage is in the honest assessment that precedes it. In being willing to look at a situation where most of the external signals are positive — where people are telling you that you are doing well, where the compensation is strong, where the role is prestigious — and saying: this is not the right container for what I am becoming.

That assessment requires a degree of self-knowledge that most professional environments actively work against. Organizations, by their nature, reward people for being what the organization needs them to be. The longer you are inside a particular institution, the more your identity becomes entangled with its identity. Separating those two things — understanding who you are independent of the role you hold — is genuinely difficult work.

What I Have Learned from Executives in Transition

In the years since I moved into consulting and advisory work, I have sat across from a lot of executives who were navigating some version of this question. Leaders who had built significant careers inside significant institutions and were trying to figure out what came next.

What I have observed, consistently, is that the executives who navigate these transitions well share a particular quality. They are honest about their own restlessness. They do not pathologize it or try to manage it away. They treat it as information — as a signal worth taking seriously rather than a problem to be solved.

They also tend to have invested, over the course of their careers, in relationships and perspectives that exist outside their primary institutional context. They have maintained friendships with people who know them as people rather than as role-holders. They have sought out experiences — travel, conversation, exposure to different industries and cultures — that give them a reference point beyond their own organization's walls.

That investment pays dividends precisely in moments of transition. When the institution no longer fits, the executives who have built that kind of external scaffolding have somewhere to stand while they figure out what comes next. The ones who have not can find themselves surprisingly unmoored — successful by every conventional measure, but uncertain about who they are when the title is removed.

The Question Worth Asking

I do not think the goal is to leave institutions. Institutions matter. They are where large-scale change happens, where resources are marshalled, where the kind of sustained effort that produces lasting results becomes possible.

But I do think the goal is to be honest — genuinely, rigorously honest — about whether the institution you are in is still the right one for the work you are most equipped to do and the leader you are still becoming.

That question is worth asking regularly. Not in a spirit of restlessness for its own sake, but in the spirit of the kind of honest self-assessment that separates executives who keep growing from executives who plateau.

The room you are in shapes the thinking you do. The institution you belong to shapes the problems you see and the solutions you reach for. Choosing that room deliberately — rather than simply remaining in it because you arrived there and it has been comfortable — is one of the most consequential decisions a leader makes.

And it is a decision that deserves more honest attention than most of us give it.