Don't be a TSA Agent

A few weeks ago, I was rushing through the airport trying to catch a flight to NYC.

I walked up to security with my usual confidence/arrogance.

“Shoes off?” I asked the TSA agent.

He gave me that dead-eyed look of someone who’s repeated the same instructions 500,000 times a day since 2003.

“No, keep your shoes on. But belt off, pockets empty, laptop out,” he said, monotone.

I nodded. Did most of that.

But as my bag rolled through the scanner, the conveyor stopped.

“Sir, all electronics larger than a cell phone need to come out,” the agent called.

I had left my iPad in the bag.

Rookie mistake.

The line behind me groaned. The agents shot each other that look: Another amateur.

And they weren’t wrong.

Here’s the thing: they do this every day. I fly maybe once every few months.

For them, it’s brushing teeth. For me, it’s a maze where the rules change slightly every time.

As I clumsily repacked, I had a thought:

How often do we become the TSA agent in our own businesses?

You know your product inside and out. Every feature. Every shortcut. Every best practice.

Your customers?

They dip in occasionally. They don’t live inside your software. They don’t dream about your dashboard layout. They’re trying to do a thing and move on with their day.

This mismatch creates what I’m calling: The TSA Trap — when experts judge tourists for not knowing what feels obvious.

Examples:

• The mechanic who can’t believe you don’t know what a timing belt is

• The software company that hides key features behind six clicks

• The mortgage broker tossing around acronyms like “PMI” and “DTI” like it’s common sense

• The Airbnb host with a 6-step coffee machine and zero instructions

The TSA Trap leads to frustration, friction, and churn.

It makes people feel stupid. And they’ll avoid feeling stupid more than they’ll avoid spending money.

The fix?

Stay humble.

Here’s how:

• Watch new users struggle. Don’t help them. Just observe. That’s your roadmap.

• Document the “obvious.” If everyone’s asking the same “dumb” question, it’s not dumb. It’s your fault.

• Simplify everything. If it’s hard to explain, it’s probably badly designed.

• Remember what it’s like not to know. That’s where empathy — and great design — starts.

So next time you catch yourself thinking, “How could they not know this?” — that’s your signal.

You’re in the TSA Trap.

Get out of it.

Podcasts of the Week:

Spotify:

Apple Podcasts:

Yallah Habibi,

Jon

Sagan Review of the Week:

Book a time to talk to us about your hiring needs here!