Why Autopilot Mode Can Cost You

Yesterday I spent the day inside Jefferson City Correctional Center, a maximum security prison in Missouri. You can’t bring a phone into the facility, so from the moment I walked through the first gate I was completely off the grid. No notifications and no email waiting in my pocket. For an entire day I was fully present with the people in that room, and it was one of the more alive conversations I’ve had in a long time. And, I got to share the message of Die Empty with many people who are trying to re-calibrate around what building a body of work can look like behind bars.

Then I got dropped off at the airport hours early, still turning the day over in my mind.

I went through security the way I always do.

I found my gate the way I always do.

I sat and waited the way I always do.

And when they called my group to board, I stepped up to the podium and discovered... I had never checked in for my flight.

Worse, it was too late to check in! The agent told me I would be rebooked on the first flight the next morning, which would have put me on the ground long after the Creative Leader Roundtable I was scheduled to lead at noon today.

I've never been so close to begging someone to show mercy. A manager walked over, gave me a stern look and a sterner warning, checked me in, and sent me down the jet bridge.

I got lucky. But here's the funny thing, as I reflected on it: I wasn’t distracted. I wasn’t rushing. I was doing all the right things in the wrong order, because I was just running the routine. I was on autopilot. But because of that, I skipped the most important step: telling them I was actually going to be on the flight.

Most of the time autopilot costs us almost nothing. Maybe we miss the exit and turn around or we skip a step and go back for it. Usually, the mistake is reversible and the day carries on.

But some moments only come once. The idea that arrives while you’re driving and evaporates because you assumed you’d remember it. The conversation you move through quickly because you’re certain there will be a better time later. The opening that appears in a meeting and closes again because you were executing your plan instead of reading the room.

Those moments don’t wait for you to snap out of it. There is no manager standing by to wave you through.

The strange thing is that I was more present in a place designed to strip away every convenience than I was in a place designed to give me all of them. Take away the phone and the noise and the option to be somewhere else, and attention becomes the only thing left to give. Give me all my tools back, and I nearly missed my flight.

So spend a few minutes this week walking through the places where autopilot tends to hide.

Start with your craft. When was the last time you solved a problem in a way you've never tried before? Are you running the same three moves on every project and calling it "experience"?

Look at your calendar. Which recurring meeting has not changed in two years? Ask what would actually break if it disappeared next month.

Look at the people who report to you. Whose potential did you assess eighteen months ago and never reassess? It is possible to keep managing a version of someone who no longer exists.

Look at your closest relationships. When did you last ask someone close to you a question you didn't already know the answer to? Familiarity is the most comfortable kind of autopilot (and the most expensive one!)

Look at what you say yes to. Which commitments are you still honoring out of momentum rather than conviction? You made that decision as a different person, for different reasons, in a different season.

Look at how you observe the world. Have you read anything in the last month that made you uncomfortable, or does your stimulus feed just affirm what you already believe?

Finally, look at how you begin your day. Do you spend your first ninety minutes on something that matters, or are you just drifting into your day on autopilot?

Pick one. Interrupt it on purpose. Do it slower, or differently, or with someone watching. And if you'd like, hit reply and tell me what you noticed. I read every response.

The routine will always get you to the gate. It just won’t tell you when you’ve missed something.

Have a great week!

Humanizing Work in the Age of AI (The Infinite Lever)

P.S.  I have a new workshop and keynote about how to ensure we protect the human element of our work in the age of AI. It's about how to establish principles for using new tools while deploying what makes human creativity invaluable. If you think that topic would be a fit for your organization or event, feel free to reach out through toddhenry.com/contact.