I Feel Stupid Now

By Mark Sentell · November 5, 2026 · 5 min read ·

A single man reading at a long table in a vast, otherwise empty library reading room.
New York Public Library reading room, 1911. Public domain, via Wikimedia Commons.

Every few days somebody sends me another article about another company that’s using AI.

They mean well, and they’re excited. And every time, I feel like I’m behind.

That’s a strange feeling for me, because I’m near the front of this. In my day job I lead engineering teams that build software, and we use AI constantly. If anyone should feel caught up, it’s me. I don’t.

Then I noticed something about those articles. The person sending one is usually admiring somebody else. They feel behind too, which is why they sent it.

So if you feel behind, the first thing to know is that almost everyone does. The pace of this change pretty much guarantees it. Nobody is caught up. Some people are just better at hiding it.

This is the second article in a series on the human side of the AI shift. The first article was The Computer Works for Us.

It feels a little unfair

In my first article, I admitted I’m a little jealous that AI can write better code than I can on my first try. Let me explain why.

I learned my craft the hard way, over decades. Through late nights and broken systems and bad decisions and the slow pile-up of things you only know because they once went wrong on your watch.

Now a machine can reach into the combined knowledge of humanity and bring the best of it to bear in seconds. It didn’t have to pay for any of it like I did.

Honestly, that feels a little unfair. If you’ve spent twenty years getting good at something and felt that sting, I don’t think you’re being petty. You’re grieving something real, and it’s okay to say so.

What’s still yours

The comfort I’ve found is that when it produces something for me, I was the one who asked for it.

I knew what to ask. I could see the problem. I could describe it in a way the computer would understand, and I could look at the answer and tell whether it was any good.

That’s not nothing. That’s most of the job. The years of learning the hard way are exactly what let me ask the right question and recognize the right answer.

You’ve made this shift before

Then I remembered I’d been through something like this before.

When I moved from individual contributor to manager, I had to make a hard mental shift. I did less myself and got more done through other people. For a while that felt like losing something. I missed doing the work with my own hands, and I wasn’t sure what my contribution was anymore.

Eventually I made peace with it. Producing through other people is still producing. It’s just a different skill.

The AI shift asks for the same move, from solo producer to producing through others, and being okay with that. If you’ve ever led a team, raised kids, or coached anybody, you already know how to do this. You’ve just never done it with a machine.

The room full of acronyms

Now for the part that’s harder to admit.

I’m one of those experienced people who doesn’t ask questions anymore.

When I’m in a room with people fresh out of college and they’re talking about tools I’ve never touched and ideas I’ve never heard of, I stay quiet. The jargon is even worse. Acronyms fly around the room, and unless you’re reading the same articles they are, you fall behind.

In technology, and really in any kind of knowledge work, you get judged by what you know. It’s what you’re paid for. So saying “I don’t know” can feel expensive, like admitting you’re worth less.

So we nod and smile and say we’ll look it up later. Usually we don’t.

Try a lighter posture

A humble, lighter posture works a lot better than trying to bluff. Something like:

  • “I haven’t seen that. Would you show me?”
  • “Man, things are changing a whole lot faster than I am. Send that to me so I can catch up.”

A little self-deprecation goes a long way. Saying your insecurity out loud takes away most of its power, and it might even open the door to actually learning the thing.

The wink

I use this one all the time.

In a meeting, I’ll say, with a bit of a wink, “Sometimes I just ask stupid questions to help draw out the conversation, in case someone else didn’t really understand.”

Then I ask my question.

The wink does two things at once. It lets people know that yes, I didn’t understand either. And it disarms everybody else in the room who was afraid to ask. More often than not, somebody looks relieved, and sometimes the person explaining realizes they weren’t as clear as they thought.

One honest question can make the whole room smarter.

Being known is better than knowing

As a Christian, I find a lot of freedom in this line from the apostle Paul: “Knowledge puffs up, but love builds up. If anyone imagines that he knows something, he does not yet know as he ought to know. But if anyone loves God, he is known by God” (1 Corinthians 8:1–3).

Knowledge was never meant to be the foundation of who I am. It’s useful and it’s good, but it’s always partial, and in this season it’s always a little out of date. What holds me up is that I’m known.

There’s an old proverb that fits the meeting room pretty well: “When pride comes, then comes disgrace, but with the humble is wisdom” (Proverbs 11:2). The humble guy is usually the one who learns something.

You don’t have to share my faith to take the point. If your worth comes from always being the smartest person in the room, you’re in for a world of hurt. But if it comes from something steadier, you can afford to say “I don’t know,” and you’ll grow faster than the people who can’t.

What to do this week

Admit you feel behind, to one person. You’ll probably find out they feel the same way.

Ask one “stupid” question in a meeting. Wink if you need to. Watch who looks relieved.

Remember what’s still yours. You know what to ask. You can recognize good work. That came from years you didn’t waste.

And the next time someone sends you another article about how everybody else is using AI, go ahead and read it. Just remember they’re probably feeling behind too.

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