"What If I Hit Somebody?"

The bedtime question no AI can answer for you.

Hunter always asks “Can we just ask your glasses to answer the question?”

I had one of those days.

The kind you’d show to your younger self as proof that the work was worth it.

I led a virtual session at a major speaking event and got to share the stage with Phil M. Jones, one of the best communicators alive.

Just the two of us, roleplaying live in front of 300 people. (Phil, thanks bro, that was a blast)

Real estate agent Drew, the version from a decade ago, would have given a kidney and a commission check to be in that room.

And there I was, running the whole thing in a blazer on top and basketball shorts on the bottom, like every other serious professional in the post-2020 era.

People said great things afterward, the kind of things you replay in your head while pretending you’re too humble to replay them.

It t’was a was a good day.

Then I came downstairs for our Thursday night dinner at Miller’s Ale House, which is a Thompson family ritual every week all the while, our 3 kids were running on that feral, post-6 PM energy that scientists have yet to explain.

After dinner, I put my son Hunter to bed…and if you’ve ever put a kid to bed, you know the deal.

It’s not a routine, it’s a filibuster, a philosophical inquiry disguised as stalling tactics.

Can I have water?

Why is the moon out during the day sometimes?

What would happen if a shark fought a bear?

I was halfway through the tuck-in when he stopped me cold.

“Dad. You said you’ll always be proud of me?”

“I will.”

He paused and looked at me like a tiny district attorney about to present exhibit A.

“What if I hit somebody? Would you be proud of me then?”

I nearly laughed. “Hunter. Come on, dude.”

But he wasn’t joking. He needed an answer.

And kneeling beside his race car twin sized bed, in his dark bedroom faintly lit by a rotating nightlight, my six-year-old had just asked me the most important question in my professional life.

Do I still count when I’m not good?

If you’ve built something, whether it’s a business, a career, or a life you’re proud of, you know that question lives in the walls of everything you do.

We just never say it out loud.

It’s there when you deliver a keynote and immediately check your phone to see if anyone posted about it. (I did that yesterday, by the way. I’m not above this. I’m deeply, embarrassingly not above this, but I’m human.)

It’s there when a deal closes and the first thing you feel isn’t satisfaction but relief.

And it’s there at 4 AM when the voice in your head isn’t strategizing anymore, it’s auditing.

Am I still enough if the next one doesn’t land?

The unspoken operating system behind most ambition isn’t “I want to win.”

It’s “I need to keep winning so I don’t have to find out what I am without it.”

Hunter doesn’t know any of that yet, he just wants to know his dad is proud of him even on the days he gets it wrong.

The kid is ahead of most of us.

I’ve written before about using AI as a thought filter, about dumping your raw, unprocessed anxiety on a machine before you dump it on a human.

Btw, I use it almost daily, and it works.

But Hunter’s question lives in the place after the filter.

AI can take your 11 PM spiral and hand you back clarity.

It can draft the email you’re too angry to write.

It can tell you what to say, what to do, even what you’re probably afraid of.

What it cannot do is tell you that you still matter when the scoreboard is ugly. That’s a human job, and the most important human who needs to do it is you.

Every tool we have now is designed to close the gap between idea and execution, and they’re extraordinary at it.

But no tool closes the gap between achievement and self-worth.

IMO That gap is as wide as it’s ever been…maybe wider.

Because when you have every advantage available and you still feel like it’s not enough, you can’t blame the tools anymore.

You’re just left standing in Hunter’s bedroom, asking the question.

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So here’s what I’ve started doing.

Every night, after the kids are down and the house goes quiet, I ask myself one thing. I call it the Hunter Check.

Would I be proud of the person I was today, even if none of it had worked?

Not what I accomplished.

Not whether I hit my targets.

Just whether the person behind the performance was someone I’d be proud of.

In a world where AI can optimize every output, that question might be the most important skill we have left. The machines are getting better at everything measurable, but your job is to get better at the thing that can’t be measured.

···

I told Hunter the truth that night.

“Buddy, I’d be proud of you no matter what. Even on your worst day. But I’d also help you fix it, because being proud of someone and holding them accountable aren’t opposites. They’re the same thing.”

He thought about it for a second.

“Okay. Can I have water?”

The tiny philosopher had left the building and the tiny “Chris Voss” negotiator was back.

···

Tonight, try the Hunter Check.

One question and be honest.

And if you want to go deeper, open your AI and tell it: “I’m going to describe my day. Don’t optimize it. Help me separate what I did from who I was.”

Let the machine do what it’s good at.

Then do what only you can do.

Decide that you count, even on the days you miss.

Be like Hunter…ask the hard question, and then ask for water.