Valley of Stupidity: More Knowledge, Less Confidence

So this happens a lot.

I’d come across something interesting. Decide I want to write about it. Start more research on it.

But the more I learn about it, the more I learn how little I know about it.

Wait a minute… I actually don’t know what I’m talking about.

The more I learn about something, the more unqualified I feel to write about it.

I’d feel like an impostor.

Turns out this is pretty common. 


The Dunning-Kruger effect reflects initial high confidence despite knowing so little.

As you become self-aware of your ignorance, you start to descend into the valley of despair. During which, you feel less confident even though you objectively know more than before.

Valley of despair sounds too dramatic though. I prefer calling it the Valley of Stupidity.

Impostor Syndrome is the inverse of Dunning-Kruger.  It’s feeling out of your depth despite actually knowing something.

Atlassian co-founder Mike Cannon-Brookes did an excellent TED talk on this. 


So what?

First, when I talk to someone that sounds overly confident about something, I ask myself, “Have they long passed Mt. Stupid or are they still making their way up?

It’s not always obvious. Some people are just so well-spoken. But once you ask how they learned of this and throw some follow-up questions, you should get a rough idea.

I don’t do it all the time of course. That would be exhausting. But I’m more likely to if they say something that contradicts something I read elsewhere. If I’m convinced they’re on Mt. Stupid, I’d still listen because it’s interesting hearing their perspective.

Second, I’d apply the same sniff test on myself.

If I feel really confident but haven’t yet passed through Stupidity Valley, I’d raise a red flag. And take more cautions not to do anything stupid with my incomplete knowledge.

One litmus test is if I find that I’m not able to articulate something clearly, then I probably don’t understand it well enough. Clarity in communication first requires clarity in thought.

Refraining myself is harder than it sounds though – I still end up offering opinions on topics I’m grossly under-qualified for. Which is why it’s so important to have friends that call you out on your bullshit.

Third, when I do descend Mount Stupid for a given topic, I’ve learned to do it in a safe and enjoyable way. 

But embracing stupidity is much harder than it sounds.

Descending Mount Stupid

I’ll admit I like feeling smart. Don’t we all?

Colleague: “Hey Daesol, how do you do an INDEX MATCH on multiple conditions again?

Me: “SUMPRODUCT(–(output array)*(input array 1 = condition 1)*(input array 2 = condition 2))

Colleague: “Genius. Thank you.

Feels good. I’m awesome. Dopamine hit.

But I’ve grown increasingly fond of feeling stupid too.

You know, those moments when you feel like an idiot. When you feel small. Naked. Feeling like the stupidest guy in the room.

I’ve grown to like that feeling over time.

Most people don’t like being told, or finding out that they’re wrong. But such a mindset breeds the perfect conditions to remain perpetually stupid.

This notion has been expressed by many others before.

“The more I know, the more I know that I don’t know” – Socrates

“Stay hungry, stay foolish” – Steve Jobs, 2005 Stanford commencement speech

“The biggest mistake I see smart people making is assuming that they’re smart. They’re not.” – Elon Musk, conversation with Jack Ma (Sep19)

How does one re-wire themself to feel good from feeling stupid?

I’ve tried two approaches.

Approach 1: remove the negative feelings

The default emotions that come from low confidence are usually negative. Expel this negative sentiment. Brute force the negative out, and brute force the positive in.

But this is exhausting. It’s unsustainable. It lingers. And it just doesn’t really work.

Approach 2: transform the negative feelings

Rather than rejecting a negative emotion, embrace it. Acknowledge it. Work with it. 

Have confidence about your inconfidence. Therefore, be confident on a higher dimension.

Recognize that descending into the Valley means you’re making progress, despite your primitive mammalian emotions telling you otherwise.

Recognize the difference between actually being smart and feeling smart. Remember you care more about getting it right than being right.

I’ve found this kind of zen-Buddhist-style school of thought really effective with managing emotions.

“Western medicine emphasizes surgery too much. Doctors want to take out the things that are not wanted. When we have something irregular in our body, too often they advise us to have an operation. The same seems to be true in psychotherapy. Therapists want to help us throw out what is unwanted and keep only what is wanted. But what is left may not be very much. If we try to throw away what we don’t want, we may throw away most of ourselves. Instead of acting as if we can dispose parts of ourselves, we should learn the art of transformation. We can transform our anger, for example, into something more wholesome, like understanding. We do not need surgery to remove our anger. If we become angry at our anger, we will have two angers at the same time. We only have to observe it with love and attention. If we take care of our anger in this way, without trying to run away from it, it will transform itself.” – Thich Nhat Hanh, Peace is Every Step

Cyclic Mountains and Valleys?

Maybe it just never ends and you trend upwards with higher-highs and lower-lows. At least this is what it feels like for me for most topics.

If this is true, it’s even more important to recognize when you’re being over-confident, and know how to enjoy rather than tolerate the descent into the Stupidity Valleys. Because all this might just keep on going.

Meanwhile, I haven’t fully mastered the ability to feel good when feeling stupid. So in some ways I feel like an impostor writing about impostor syndrome. Which if you think about it is kind of the point. Isn’t it?

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