Aug. 29, 2026

Autopilot (How I did everything right, and still almost missed my flight...)

Autopilot (How I did everything right, and still almost missed my flight...)

In this episode, we explore the subtle dangers of drifting through our routines on autopilot—even when we feel present and focused. After an immersive experience inside a maximum-security prison where distractions were stripped away, we reflect on the moments in life and leadership when attention is our most valuable currency. A near miss at the airport—ironically due to being unplugged and undistracted—sparks a deeper look at how easily critical details slip through the cracks when we trust our routines more than our awareness.

We unpack specific areas where autopilot often hides in our creative and leadership work: our craft, calendar, relationships, commitments, worldview, and daily rhythms. This episode challenges us to disrupt comfortable patterns and purposefully introduce friction, in order to foster real presence and creative breakthrough.

Five Key Learnings

  1. Autopilot Feels Like Competence—Until It Isn’t. We can go through the motions perfectly and still miss crucial steps, simply because we’re following routine, not engaging consciously.
  2. Some Missed Moments Aren’t Reversible. Unlike a missed exit or an ignored notification, real opportunities—whether creative ideas or key conversations—may only come once.
  3. Comfort Can Make Us Lazy Observers. Familiarity with our teams, habits, or content feeds can lull us into leading outdated versions of reality, missing potential or growth.
  4. Interruption Is Sometimes the Only Solution. Deliberately changing our pace, asking different questions, or doing tasks in a new way can wake us up to what routine has dulled.
  5. Attention Is the Most Limited Resource. Especially in environments stripped of distraction, we realize just how powerful and rare undivided attention is—for ourselves and for others.

Learn more about speaking and workshops at ToddHenry.com/speaking

Find Todd Henry's books at ToddHenry.com/books

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Todd Henry [00:00:02]:

Hey friends, welcome to Daily Creative. My name is Todd Henry. Hey, before we dive in today, I want to let you know that I have a new series of workshops and talks that I've been delivering around how to humanize AI. How do we make this transition as creative pros into a world where we're increasingly relying on machines to help us ideate and collaborate? How do we do that in a way that allows us to remain human? And I have some principles I've been teaching around something I call the infinite lever. So if that would be a fit for you or your organization, feel free to reach out through toddhenry.com. Would love to see you there. Yesterday, I spent the day inside of Jefferson City Correctional Center, which is a maximum security prison in Missouri. You can't bring a phone into the facility.

 

Todd Henry [00:00:51]:

And from the moment I walked in the gate, I was completely off the grid all day. from 7:30 AM until about 4:00 PM when I left. No notifications, no email waiting in my pocket for an entire day. I was just fully present with the people in that room. And it was one of the more alive conversations I've had in a long time. We were sitting at tables with people who had, some of them had been in prison for decades, uh, and just talking about life and talking about leadership. It was part of a Global Leadership Academy event put on by Beau Cornelius, who I've interviewed on the podcast before. And I got to share the message of Die With many people who are trying to recalibrate around what building a body of work can look like behind bars.

 

Todd Henry [00:01:34]:

Anyway, after the event, I was in the car and Beau actually took me to the airport. I got dropped off at the airport hours early. I mean, like 3 hours early. I was flying out of Columbia, Missouri, which by the way has like 3 flights a day. So I got there, the TSA agents were laughing at me because I got there comically early for my flight. And I was still turning the day over in my mind. And I went through security like I always do. I was the only person there.

 

Todd Henry [00:01:59]:

I found my gate the way I always do. I sat and I waited the way I always do. And then they called my group to board and I stepped up to the podium and I realized I had never checked in for my flight. Worse, it was too late to check in. Our plane was almost boarded. There were 3 people waiting to board. Everybody else had already boarded. And the agent told me, I wouldn't be able to get on the flight.

 

Todd Henry [00:02:26]:

I was going to be rebooked on the first flight the next morning, which would have put me on the ground long after my creative leader roundtable I was scheduled to lead at noon on Friday. This was on Thursday. On Friday, I led a creative leader roundtable and I have never been so close to begging someone to show mercy. A manager walked over, gave me a stern look and a sterner warning. And he asked me, when did you get to the airport? I said, like 3 hours ago. I've just been sitting here for 3 hours. Uh, and he said, this is a one-time thing. He checked me in and he sent me down the jet bridge.

 

Todd Henry [00:02:59]:

I was so grateful. Thank you, manager at Columbia, Missouri Airport. Anyway, 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, but I did them in the wrong order because I was just running the routine. Now, normally, If my phone had been on me, I would have received pings throughout the day. Hey, it's time to check in.

 

Todd Henry [00:03:22]:

Hey, your flight's coming up. Hey, don't forget your flight. And I would have already checked in easily, but I was, because I had been checked out, once I finally got my phone back, I was just on autopilot. Because of that, I skipped the most important step, telling them that I was actually going to be on the flight. Now, most of the time autopilot costs us almost nothing. Maybe we miss an exit and we turn around, we skip a step, we go back for it. Usually the mistake is reversible and the day carries on, but some moments only come once. And that was what I almost experienced.

 

Todd Henry [00:03:56]:

The idea that arrives when you're driving and it evaporates because you assume you'll remember it. The conversation that you move through quickly because you're certain there will be a better time later to have that conversation. 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's no manager standing by to wave you through. The strange thing is I was more present in a place that's designed to strip away every convenience than I was in a place designed to give me all of those conveniences. Take away my phone and 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 because I was on autopilot.

 

Todd Henry [00:04:40]:

I assumed my tools would do things for me. So here's the challenge. Here's what I want you to consider this week. Spend a few minutes walking through places where autopilot tends to hide. Start with your craft, whatever that is— design, writing, maybe it's leadership, maybe it's marketing. When was the last time you solved a problem in a way you've never tried before? Are you running the same 3 moves on every project and calling it quote unquote experience? Look at your calendar. Which recurring meeting has not changed in 2 years? Ask what it would actually look like or what would actually break if it disappeared next month. If nothing, then it's probably just autopilot for you.

 

Todd Henry [00:05:22]:

Look at the people who report to you. Whose potential did you assess 18 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 it's often 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 the decision as a different person for different reasons in a different season. So what are you saying yes to? That you did on autopilot? 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.

 

Todd Henry [00:06:17]:

Do you spend your first 90 minutes on something that matters, or are you just drifting into your day on autopilot? So I encourage you to pick one of these things or pick something else, but interrupt something on purpose. Do it slower. Do it differently. Do it with someone watching. And if you'd like, let me know what you noticed. I would love to hear from you. You can send your responses to email@ToddHenry.com. I would love to hear from you.

 

Todd Henry [00:06:45]:

Listen, the routine will always get you to the gate. It just won't always tell you when you've missed something. Interrupt autopilot. Before it interrupts you. You can do everything right and still almost miss your flight. Hey, thanks so much for listening. As I mentioned, would love to hear from you. Feel free to send me an email.

 

Todd Henry [00:07:10]:

Uh, let me know ways in which you're disrupting autopilot in your life. If you want the email version of this, you can get it. I send out an email every single week. Many of them contain these essays that I'm reading to you now. You can get that at toddhenry.com/start. That's toddhenry.com/start. And if you'd like to support the show or support my work, you can purchase one of my books at toddhenry.com or anywhere you buy books. And, uh, if you would like also to bring me to your organization, I do dozens of keynotes and workshops a year on how to lead creative people and also how to be human in an age in which we are increasingly moving toward machines.

 

Todd Henry [00:07:51]:

Don't we all need to do that? All right. Thanks again for listening. Until next time, may you be brave, focused, and brilliant. We'll see you then.

Todd Henry Profile Photo

Author

For nearly 20 years, Todd Henry has equipped leaders and creative pros to become the most valuable person in any room.

He is the author of seven books (including The Accidental Creative, Die Empty, and Herding Tigers) which have been translated into more than a dozen languages, and he speaks internationally on creativity, productivity, passion for work, and generating brilliant ideas. Todd’s podcast Daily Creative has been downloaded more than 20 million times since 2005.

Over the years, Todd has developed a comprehensive framework that empowers leaders and creative pros to produce brilliant work in healthy teams that make a meaningful difference in the world. Through his keynotes and workshops, he shares practical strategies to help people and teams to be brave, focused, and brilliant every day.