The Dangers of Autopilot

or "Acai Bowls, again!?"

There’s a deli near us that drags out the same folding sign every day. It always says the same thing: “Open. Acai Bowls.”

I’ve lived here for years and that sign has not changed once. Not once in at least three years.

Every time I drive by, I imagine the person dragging it out. Not giving it a second thought. Not thinking if it is still the best sign they can use. Just going through the motions. Do they even have acai bowls anymore? Have they added anything new to the menu in the last 3 years? Are their acai bowls really special? Do they even think about what they put on that sign?

And then I realized: I’ve been that person. In meetings. After nearly seven years running Bitly. With my team. With my board. Walking in, saying the same things, going through the motions, not actually leaning in and trying to do my best work.

That’s one of the traps of leadership. Not failure. Apathy. The slow slide into lethargy, where you’re technically “open” but not really alive. Where you’re showing up, but nobody, including you, feels any energy.

I’ve coached enough CEOs to see this pattern over and over. It’s not burnout. It’s autopilot. And autopilot is dangerous, because it feels harmless in the moment. But it compounds. Your team notices. The culture shifts. Meetings get duller. Decisions get softer. You wake up one day and realize you’ve been dragging the same damn acai bowls sign out for months.

What’s helped me avoid this is creating rituals like my Friday Updates and Sunday To Do Lists. The Friday Updates weren’t just a status report but a tool to drive focus and urgency for me and the company. It reminded everyone, including me, what mattered most right now.

My Sunday To-Do List served a similar purpose. It forced me to think ahead, to be clear with myself about priorities, and to walk into Monday ready to lead instead of react.

Preparation has been another anchor. Before a meeting, I don’t just skim the deck on the way in. I ask myself: what do I want people to walk out knowing, deciding, or feeling? I even try to do a little mentalizing. That one minute of intention changes everything.

That’s the difference between dragging the sign out front and actually running the store. One is autopilot. The other is leadership. Your team doesn’t need you to be perfect; they need you to be awake. To show up with clarity, focus, and urgency. Because if you keep putting the same sign out every day, sooner or later nobody even bothers to look.

If this post helped you, or made you think of someone, please consider forwarding it to them. And let me know what resonated or missed. I read every reply.

###