The Map You Make While Walking

“I think I’ve been looking at the wrong thing entirely.”

A client came to our first session last spring with a printed document. Twelve pages, tabbed. There was a skills inventory, a gap analysis, a list of target industries ranked by alignment with his values, and a twelve-month timeline broken into phases: research, upskilling, outreach, transition.

He’d spent six weeks on it.

I read through it while he watched. The work was genuine — careful, thorough, the product of someone who’d taken his situation seriously. We spent most of that first session going through it together, and most of the second.

By the third session, the document was fourteen pages. He’d found a new framework online and reorganized the skills section. He’d added a fourth column to the industry rankings.

He still hadn’t spoken to anyone working in any of those industries.

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Near the end of that third session, I asked what he thought would happen if he had one coffee — not to ask for anything, just to talk — before we next met.

He went quiet. Then he said: “I’m not ready yet.”

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I’ve been in this work long enough to know what that silence contains.

The document wasn’t being refined because it was incomplete. The refining was doing something the document itself couldn’t do: it was holding off the moment when he’d actually have to go. As long as he was still preparing, the transition hadn’t truly started. No attempt had been made, which meant no attempt could fail. The plan was doing exactly what it was designed to do — just not the thing its designer thought he was building it for.

This is what I find difficult to say when someone is deep in a planning document: the productivity of the preparation is part of what makes it so effective at what it’s actually doing. The skills inventory, the quarterly timeline — all of it looks like forward motion, and in some ways it is. But at some point, genuine preparation and the management of anxiety become indistinguishable from the outside, and that’s when fourteen pages becomes seventeen, and the document keeps growing without getting any closer to the door.

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I’m not describing this as a failure of character. In 2023, when I came back to Lisbon from Kyoto after eighteen years away, I made my own version of the document. Lists, sections, a loose phasing. The structure helped me feel like I was moving when I wasn’t yet sure what moving looked like. That’s a real function. The question is when structure stops serving the movement and starts replacing it.

What I didn’t understand then was that you can’t chart terrain you haven’t walked. You can describe what others have said about it, read everything written by people who’ve made similar moves, build a careful grid from the outside. The accounts and the experience are different countries. You don’t know what’s in the territory until you’re standing in it.

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This is the structural difficulty with planning a transition you can’t yet see: you’re asked to map a place you’ve never been. You build a route to somewhere you haven’t seen, through country you don’t know, using landmarks from other people’s accounts of it. So of course the plan keeps being updated. Of course new frameworks keep arriving and getting incorporated. The uncertainty of the situation keeps generating the need for more preparation, because the preparation holds the uncertainty at arm’s length. Only entering the actual situation tells you what’s in it.

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What moves people, in my experience of working through this with them, is something smaller than a plan and harder to schedule. A conversation they almost talked themselves out of having. A project they said yes to because the timing happened to work — that told them, in the doing, something specific about what they actually wanted, in a way that months of preparation hadn’t touched.

When I ask people who’ve made significant changes how they got there, the story they tell almost never matches the version they’d laid out beforehand. The planned version has a logic: research these options, develop these skills, approach these people in this sequence. What actually happened usually involves someone they met through a sideways connection, an opening that arrived while they were watching something else.

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My client with the fourteen pages eventually had that coffee. One coffee, with someone he’d known at school who’d ended up in the industry he’d ranked second on his list. The conversation went somewhere he hadn’t planned for. He came to our next session and said: “I think I’ve been looking at the wrong thing entirely.”

He’d been looking at it — carefully, thoroughly — for months. He found that out in ninety minutes.

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I’ve stopped working with transition plans after the first or second session. The plan tells me something useful: which parts of the situation feel safe enough to describe, where the anxiety is concentrating. That’s worth knowing. But the plan is almost never where the movement comes from.

What I ask instead, at some point in the work: what would the first move be?

Some people answer immediately, which usually means the answer’s been there for a while. Others go quiet. Both responses tell me where the actual edge is — which is what I want to understand, and what the plan, however detailed, rarely shows.

The question I still don’t have a clean answer to is when the right moment is to ask it. Push it too early and the person isn’t ready to hear it. Leave it too long and the preparation becomes the whole project. I get this wrong sometimes, in both directions. What I’ve stopped doing is waiting for the document to feel finished before I ask.

— Tiago

This is a newsletter about the inner experience of the AI transition. If this found you at the right moment, share it with someone who might need it.

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If you’re new here: I’m Tiago Villares, a career coach based in Lisbon. I’ve spent the last three years working with people navigating career transitions in the age of AI — and writing about what that actually feels like from the inside. My first book, “After the Wave,” is out now.

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