You're Working Hard and Going Nowhere? You Might Be Missing Someone Who Won't Flatter You
Ideas & Opinion·6 min

You're Working Hard and Going Nowhere? You Might Be Missing Someone Who Won't Flatter You

Why do some people work so hard and barely move? Something I saw while training my AI made it click: the real bottleneck in self-improvement isn't brains or effort. It's not having a judge who refuses to do you the favor of agreeing. This is about AI, but really it's about you and me.

Y
Young

You know that feeling — you're working hard, but you seem stuck in the same spot?

You read the books, took the courses, wrote the plan. Then you look at the goals you set in January, and by December they're still the same three lines.

I used to think this was a willpower problem. I wasn't grinding hard enough.

Lately I've changed my mind. And what changed it was a machine.

Something I noticed in my AI

I've spent a lot of time over the last couple of years training my AI assistant. Every time it messes up, I write a rule. Hundreds of them by now.

Then I read an article on AI self-improvement by Lilian Weng, former head of applied research at OpenAI.

She names something I'd never really thought about. For an AI to improve itself, the hard part isn't how smart the model is. It's that there's no reliable judge — no ruler to tell it whether a change actually made things better.

Without that ruler, it's just flailing. The pile of rules grows, but it isn't really getting better.

I stopped reading for a second, because that was me. I'd written hundreds of rules and never measured a single one. I just felt it was behaving better.

We do the exact same thing to ourselves

Think about who the judge is when you try to improve yourself.

It's you.

And when a person is their own judge, they do something very natural. They cut themselves slack.

"I didn't get to it because I've been slammed." "I have made progress, it's just not showing yet." "That goal was too ambitious anyway."

It's not that we don't try. It's that the ruler in our hand is one that keeps finding us a way out.

A few days before writing this, I did exactly that. I gave something I'd built a high score, then handed it to someone with no stake in it — and got taken apart. That's when I saw how generous I am with myself.

Grading yourself, you'll almost always overrate. That's not a character flaw. It's just being human.

What actually moves people is the thing that won't flatter you

When I look back at the rare times I actually grew, they all share one thing.

It wasn't that I was trying harder. It was that I happened to have a judge nearby who wouldn't go along with me.

Sometimes a friend who'd say "this isn't good enough" to my face, without worrying about offending me.

Sometimes a number. Zero sales is zero sales. It doesn't comfort you.

Sometimes a system that made me show evidence before I got to say "I did it."

All three have the same personality. They don't care how you feel. They only look at what's true.

And most of our daily life is the opposite. We're surrounded by voices that understand us, explain us, tell us we're already doing great.

Those voices feel good. They also keep us very comfortably in the same spot.

So here's what I ended up doing

I built my AI a ruler — a machine that keeps checking whether it kept its rules, and flashes red when it didn't.

It won't let me off just because I'm in a good mood. I say it's fixed, it tests it again and shows me.

Being slapped, over and over, by a machine you built yourself is not a pleasant process.

But I realized that discomfort was exactly what I'd been missing.

We spend so much energy hunting for feedback that feels good, and almost none building ourselves a judge that feels bad but tells the truth.

In the end

I'm not telling you to go find someone to yell at you, and I'm not telling you to beat yourself up daily.

I just think that if you feel stuck, don't rush to blame your own effort first.

Ask the question that comes before that.

How do you know whether you've improved? Is the ruler in your hand actually measuring — or just comforting you?

Is there anyone in your life who won't do you the favor of agreeing? Or has it been, from start to finish, just a you who's very good at finding excuses?

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