The Trap Isn’t Waiting for an AI Policy. It’s Waiting to Be Told What to Do.

A few weeks ago I wrote a line in a post here that a client brought back to me days later, almost word for word:

“If your only shot at building AI judgment is waiting for your employer to figure out a policy, you could be waiting years.”

She didn’t want to talk about AI. She wanted to talk about the sentence.

Because the real trap isn’t the AI policy. That’s just this decade’s version of it. The real trap is waiting to be told what to do — with anything. Your next skill. Your next role. Your next move. Waiting for permission, for instructions, for the “right thing” to show up on its own, while the years quietly pass and you stay exactly where you are.

I know that trap from the inside — I lived in it for the better part of a decade, and it cost me more than I understood at the time.

The Seven A.M. Shift

Two years into my staffing career, I was a supervisor at a national staffing company. I’d taken the 7 a.m. opening shift — the one nobody else wanted — because someone had to be there, and I decided it would be me. My manager usually rolled in between 10 and 11, shopping bags in tow, blaming her 40-minute commute for the gap.

One day I asked her directly: how do I grow here? Make more money, get more opportunity, do something that matters?

“Keep doing what you’re doing,” she said. That was the whole answer.

I stayed a few more months after that, on top of the two years already behind me. My raises tracked inflation and nothing else. My team had driven a 37% jump in sales — in a market growing about 12% a year on its own — and my commission was 1% of gross margin. Do that math and you’ll understand why I finally left.

I didn’t leave with a plan. I left because someone made me an offer loud enough to drown out the voice telling me to keep doing what I was doing: a 100% raise, moving from staffing supervisor to technical recruiter. Doubling my income was the only thing strong enough to override a habit I didn’t know I had — waiting for permission to want more.

The Pattern Doesn’t Care What Company You’re At

I thought I’d learned the lesson. I hadn’t. I’d just changed the furniture.

Five years into a role at another company I’d relocated for, the headquarters product job I’d signed up for had quietly turned into something else: a traveling consultant role, living out of client sites more than out of my own house, for 60% less than what I’d walked away from to take it.

I told myself that was just how corporate worked. I found a similar seat somewhere else and kept moving.

That’s where the pattern finally showed itself, whether I wanted to see it or not. Grad school had told me I was being trained to lead. My results said otherwise. My relationships — every one of them, going back years — had been consistently, quietly bad. Somewhere between that first shift and that next desk, I’d built an entire career, and most of a life, around a blind spot I couldn’t see on my own: I was waiting. Waiting for the next boss to notice me. Waiting for the next role to be different. Waiting for someone else to make the call, so I’d never have to own the outcome.

What I Was Actually Avoiding

It’s tempting to call that laziness. It wasn’t — I worked plenty. What I was avoiding wasn’t effort. It was responsibility for my own life. Underneath the waiting was something closer to existential fear: I had debts, and nobody else to fall back on if I got it wrong.

As long as I was waiting for permission, I never had to own a bad outcome. If it didn’t work, well — I was just doing what I was told.

Waiting felt safe. It wasn’t. It cost me the better part of a decade, and not just at work. The same pattern that kept me quiet at my desk kept me quiet everywhere else that mattered too.

What Finally Broke It

The break didn’t come from one bad day. It came from a phone call.

I was telling my brother how unhappy I was — at work, in my marriage, all of it. “Do something about it or quit complaining,” he said. “It’s been five years.”

“Five years? No way.”

“Oh, yes. Remember that other time you were unhappy? That was five years before this one.”

He was right. I was sitting in the same kind of car, in front of the same kind of house, after the same kind of day, having the conversation I’d already had once before — five years earlier, almost to the month.

I hadn’t just been waiting. I’d been waiting on a loop, and it took my brother saying it out loud before I could see it myself.

That’s not the same as waiting to be told what to do. Nobody assigned me that call. My brother didn’t hand me a plan — he just told me the truth because he loved me enough to say it. What I did with it was still on me.

At the time, it was all compounding. A marriage that had gone cold. A thankless job under a software development manager who made it clear from day one that I didn’t really count — he was “a technical guy,” so was his boss, so was the CIO above both of them. “You’re not a technical guy,” he told me once, like that settled the matter. I was the project manager on his team. Apparently that meant I didn’t belong in the room where decisions got made. He’d followed a genuinely good boss who’d actually helped me grow, which made the contrast worse. None of it was really separate. It was the same pattern, finally impossible to unsee.

It didn’t fix itself overnight. It took years of the same lesson landing again and again — good jobs and bad ones, good bosses and bad ones — before I actually stopped waiting and started deciding. I got something out of nearly every one of them, even the ones that hurt. I just couldn’t see it until I stopped waiting long enough to look.

Which Brings Me Back to That Sentence About AI

When I wrote that your only shot at building AI judgment can’t be waiting for your employer to hand you a policy, I wasn’t really writing about AI. I was writing about the 7 a.m. shift, the bait-and-switch, the five-year loop my brother named before I could. About every year I spent hoping someone above me would eventually say the thing that gave me permission to move.

Nobody’s coming with that memo. Not about AI, and not about your career.

If you’re waiting to be told what to do — waiting on the org chart, the market, your manager, or the “right time” — you already know how that story goes, because I just told you mine. The raises track inflation. The role quietly changes shape without your agreement. And the blind spot stays exactly where it’s always been: too close to see on your own.

That’s not a discipline problem. It’s not a sign you’re behind or broken. It’s a signal — the same one I gave off for years without knowing it — that part of you already knows the current chapter isn’t the answer, and is waiting for permission to admit it.