I was in the middle of a conversation about AI with friends — all of us senior technology leaders, all of us deep into this — when I said something I hadn’t planned to say.
“The faster this makes me, the more constraints it removes, the more I feel pressure to go even faster and do even more. Like my brain is on fire with ideas and even with this acceleration I still don’t feel like I have enough time.”
I stared at it for a minute after I hit send. It was more honest than I’d been with myself.
There’s a rhythm to senior leadership that nobody warns you about. You do the hardest thinking: the pattern recognition, the strategy, the decisions that set direction for hundreds of people. And then you wait. Not because you’re idle, but because organizations move at organizational speed. You set something in motion and watch it propagate through layers of people, processes, budgets, approvals, each one moving at the pace of human coordination. Your brain finished the problem three weeks ago. The organization is just getting started.
That gap between your processing speed and your organization’s execution speed isn’t a bug. It’s just how leading through people works. Over the course of a career, you make peace with it. You learn to pace yourself. You build philosophies around it. This year I gave my team an axiom: “achieve more by doing less.” Permission to stop doing things that don’t move the needle. You accept the rhythm the way you accept weather. Some things are just the physics of the situation.
I never spent much energy wishing it were different. I pushed on organizational constraints where I could, the way anyone does. But I mostly accepted them as hard facts. The speed of execution was gravity. You could jump, but you couldn’t fly.
Then AI changed the physics.
Not for everything. Culture still moves at human speed. People decisions still take the time they take. Building trust, reading a room, knowing when someone needs to be challenged and when they need to be carried. All of that is still slow, human, irreducible work. That hasn’t changed. I don’t think it will.
But for a specific category of work — the building, the analysis, the writing, the prototyping, the things that used to require teams and timelines — the feedback loop collapsed from weeks to hours. Sometimes minutes. An idea that would have lived in a strategy document for a quarter, waiting for resources and bandwidth, could now exist by the end of the day. Not as a plan. As a working thing.
I expected that to feel like relief.
It doesn’t feel like relief.
I’m in the middle of building something with AI, and while I’m building, two more ideas arrive. Not later. Not after I finish. While I’m still working. I can feel the pull of them, the urgency to start the next thing before I’ve finished the current thing. And because AI makes parallelization possible in a way it never was before, I don’t resist the pull. I open another window. I start the second thread. The first build produces a result that sparks a third idea. Now I’m running three streams simultaneously and my brain is already reaching for a fourth.
This is not a faster version of how I used to work. The old constraints didn’t just slow me down. They acted as a natural triage system. When execution required other people and organizational timelines, most ideas died in the queue. They had to. I couldn’t pursue them all, so my brain learned to let the weaker ones go. The scarcity of execution capacity forced prioritization automatically. I didn’t have to choose what to work on in any existential sense. The constraints chose for me.
AI removed the scarcity. And it turns out my brain was always generating at this rate. I just never knew. The bottleneck killed most of the ideas before they could demand my attention. Now nothing has to die in the queue. Every idea can live. Every idea wants to live. And I feel the pull of all of them simultaneously.
I gave my team that axiom, “achieve more by doing less,” because I believed it. I still believe it. But I’m discovering something uncomfortable about the relationship between those words and the constraints that made them easy to follow.
“Achieve more by doing less” is easy to practice when external constraints enforce the “less” part. When you can only execute three things at a time, choosing the right three feels like wisdom. When you can execute twenty things at a time, choosing three feels like waste. The idea hasn’t changed. But the emotional experience of following it has changed completely. Every idea I let go now is an idea I could have built. The constraint used to absorb that cost invisibly. Now I feel every one.
Those words worked partly because reality was doing the hard part. Now the hard part is mine.
There’s a version of this story that’s purely triumphant. I used to set strategy and put plans in motion and then wait as the organization slowly, slowly made the plans real. With AI I can be back in the driver’s seat and affect change so much faster. That’s not a small thing. It changes what a senior leader can actually do.
But the triumphant version isn’t the whole truth.
The whole truth is that I feel behind. By any external measure, I’m ahead. People who have all day to focus on this — people without the other duties and constraints of a CSO role — should be lapping me. Most of them aren’t. I’m objectively outpacing people with more time and fewer responsibilities. And I still feel behind.
I feel behind because I’m not measuring against other people anymore. I’m measuring against what’s now possible. And what’s now possible keeps expanding. The gap between where I am and where I could be is actually growing, even as I accelerate. The goalpost didn’t move. The goalpost multiplied. There are now fifteen goalposts where there used to be one, and I feel the pull of all of them.
Even writing this essay is one of them. It’s Sunday. I already published a security piece this morning. I have a personal project half-built in another window. Between paragraphs I made breakfast, had a snack with my five-year-old, worked on her barista skills — she’s getting good — and right now she’s next to me showing me the Animal Crossing character she made for me. I’m present. I’m parenting. I’m also writing this, because the idea was alive and I couldn’t let it wait. I feel like I should be tired. I’m not.
There’s a pattern in who’s actually feeling this. AI isn’t an equalizer. It’s an amplifier. It amplifies whatever was already there. A friend put it well in the same conversation: “The high performers are utilizing it and are 100x and the bulk of the folks who are just coasting are still just coasting.” AI didn’t close the gap. It widened it.
Which means the people most likely to feel what I’m feeling are the people everyone assumes are fine. The driven ones. The ones whose brains were always generating at this rate but never had the tools to act on it. From the outside we look energized, productive, ahead of the curve. From the inside we’re discovering that the curve has no end.
I didn’t wish for this. I didn’t spend my career pushing against organizational constraints, dreaming of the day they’d fall. I accepted them as gravity. And then gravity changed, not because I demanded it, but because a technology arrived that simply made it different.
And in the new gravity, I’m meeting a version of myself I’ve never met. A version that wants to run in five directions at once. A version whose appetite for building and thinking and creating has no natural resting state. I’m twenty-five years into my career, and I’m discovering something about my own mind that I had no way of knowing, because the conditions that would reveal it never existed before.
The constraint wasn’t just holding me back. It was pacing me. It was giving me a rhythm I could live inside. And this is the part that makes me pause: it was protecting me from my own appetite.
I don’t mean that in some dramatic sense. I love this. The energy is real. The joy in building is real. I am more intellectually alive right now than I have been in years, maybe ever. This isn’t a cautionary tale.
“Fun but also… who knows” is the most honest thing I’ve said about it. I’m watching myself accelerate and I’m watching myself want to accelerate more and I don’t entirely know where the new resting state is. Or if there is one.
I have two daughters. They’re watching me figure this out in real time. They see a dad who’s engaged, energized, building things, excited about his work. They also see a dad whose brain is always reaching for the next idea. Kids see everything. I don’t know yet what that teaches them about capability and presence, about what it looks like when a mind on fire tries to also be quiet in the room.
I told my team this year to achieve more by doing less. I meant it.
I’m not sure I’m living it right now.
I don’t have an ending for this essay because I don’t have an ending for this experience. I’m in the middle of it. The governor is off, and what I’m discovering underneath isn’t a problem to be solved. It’s a reality to be understood. My mind does this. It always did. I just never knew.
The question I’m sitting with is whether the governor was the obstacle or the architecture. Whether the constraints I accepted as gravity were holding me back, or holding me together.
I think the answer might be both.