When Did We Stop Letting People Figure Things Out?

The Rand McNally in the Glovebox

I started at the company I still work for as a high school intern, and one of my jobs back then was running errands around town. This was long before anyone had a phone that could tell you where to go, so I did it the only way there was. I kept a Rand McNally map in the car, and when I needed to get somewhere I'd never been, I found it on the page first, held the route in my head as best I could, and went.

I got turned around constantly. I made wrong turns, doubled back, pulled into gas stations to ask how to get back to a road I recognized. And somewhere in all of that, without ever deciding to, I learned the city. Not from the map. From getting lost in it enough times that I didn't need the map anymore.

I didn't think of any of that as learning at the time. It just felt like the annoying part of the job. But those errands were teaching me something the map couldn't, and it took me years to understand what the inconvenience had actually been for.

What the Inconvenience Was For

I've been noticing lately how much of that kind of inconvenience we've removed from people's lives, and how fast. A car now warns you when you drift out of your lane. Maps tell us exactly where to turn and when. The software finishes the sentence you were halfway through typing. Streaming lines up the next thing before you've decided you want it. Companies build processes designed to keep an employee from ever making the wrong call, and a parent can watch a dot that is their child move across a screen.

Every one of those, on its own, makes perfect sense. I wouldn't argue against a single one of them.

I wonder what happens after enough of them stack up. Technology is not making us dull, and that argument does not interest me. The better question is whether organizations sometimes make things so smooth and so efficient that they accidentally remove the small decisions through which people were gaining experience.

All those errands I fumbled my way through were doing something I never gave them credit for. They were building judgment, one wrong turn at a time. The wrong turns weren't the enemy. They were the training.

What a Process Can't Hand You

That question reaches straight into leadership. A young employee who follows a well designed process will make fewer mistakes early on. What I'm less sure about is whether that same person develops the instincts of someone who occasionally had to figure out what to do when the process didn't have an answer. Preventing mistakes does not automatically build experience, although we often talk as if it does.

I've spent close to thirty years in live production, where the plan eventually meets something nobody planned for. It happens at every show. At some point the script runs into a moment the script didn't account for, and someone has to decide, right then, with the room watching.

The people who are good in that moment are rarely the ones who followed the plan most faithfully. They're the ones who've been through enough unplanned moments to know what they'd do in the next one. You can't hand that to someone in a document. I've tried.

You can teach a person the process in an afternoon, but what sits underneath it took them years of small decisions to build, most of which looked like nothing at the time.

So the useful question for anyone building a team is not how to keep people from ever getting it wrong. It's where you can afford to let them. Which decisions are safe to hand over unfinished, without a script and without someone stepping in the moment it gets hard, because the stumble is the part that teaches. A good process protects the outcomes that can't absorb a mistake and deliberately leaves room around the ones that can.

Judgment does not transfer through instructions. It gets earned through thousands of ordinary decisions, and many of those decisions only exist because something did not go smoothly.

When we smooth the path so completely that no one can stumble, we may also be taking away the moment a person would have looked at a problem, realized no one was coming to solve it, and figured out what to do anyway.

The Long Way to Crawford

Years later, my wife and I were driving from Aspen back to Denver to catch a flight home. An accident closed the road we were supposed to take, and the only way through sent us west, around the back of the mountains behind Maroon Bells, into an area with no cell service at all.

No phone to reroute us. Just a road heading south and the same instinct I'd built running errands as a kid, keep going, pay attention, something will eventually cross back east.

We stopped at a gas station in Crawford, Colorado to ask for directions, nowhere near where we meant to be, at the end of one of the most beautiful drives either of us has ever taken. We'd never have found it on purpose. We only found it because the plan broke and nobody was there to smooth it over.

What stayed with me had almost nothing to do with getting home. That gas station is where I first tried Coca-Cola Coffee, which is a ridiculous thing to remember about a trip and yet one of the first things I do.

And I got curious about the town while we were there, curious enough to learn that little Crawford is where Joe Cocker spent his last years and is buried. I hadn't meant to be in that town for a single minute. I left knowing things about it I'm still glad I know.

A working phone would have fixed the whole trip. It would have found the detour, kept us on the fastest line to the airport, and we'd never have seen Crawford at all. It would have solved the problem perfectly, and taken the best part of the day without either of us knowing it was gone.

I can't get past what else disappears with those wrong turns. We lose some of the judgment they build, but we can also lose the things we would only have found by being lost: the beautiful drive, the coffee, and the small town with its own history. We do not even get to know what we missed.

The question is whether we still believe people can find their own way, and whether we are willing to let them be a little lost long enough to learn how and find what they were never looking for.

That belief is getting harder to hold onto, because every year there's one more tool built to make sure no one ever has to. I just hope we remember what the wrong turns were doing for us, back when we still had to take them.