88. Is it better to be underestimated or overestimated?

Don’t worry about the picture. It’s about underestimating someone.

I’ve just had a breakthrough in understanding — both of myself and of others. I’m still not completely sure what to do with it, but it feels kind of profound.

Yesterday, I wrote a blog post. Some people found it insightful. Some people found it provocative. One of my good friends got hopping mad about it. This sometimes happens when I post something. In such cases, heated discussions follow, and there’s always something to be learned.

In this case, the aha-moment came when I was talking to my wife, Marie, about the whole thing. It’s been a standing joke-with-truth-at-its-core in our marriage that I tend to overestimate people’s capabilities, mental health and power, while she tends to underestimate them. I’ll be convinced that someone is doing just fine, and she’ll be sure they’re on the verge of a personal crisis. I’ll say “Of course she can do that” and she’ll say “I really don’t think she can”.

Often, we land somewhere in the middle, and while there’s no clear-cut ratio of who’s more wrong, it leads to interesting talks about both ourselves and the world.

Yesterday, spurred by the debate that followed my post, we talked about this again, and I realised something critical.

Marie prefers it when people underestimate her.

I prefer it when people overestimate me.


That’s damn interesting, we both thought, so we tried to pick it apart and find out what’s in play there.

What followed was a long and complex discussion, but here are some of the highlights.

Of course, neither of us are objectively right or wrong in our way of approaching the world. We each struggle with our respective demons, and we each try to grow better at dealing with the world.

The reason this was such a breakthrough to my understanding was that I hadn’t realised the underlying mechanics. I’ve always felt that I insulted people by underestimating their capabilities, and I’ve never grasped that the meaning of phrases like “Who are you to judge me?” wasn’t necessarily what I thought.

I’ve always thought that expressions like that were to say:

“Who are you to make a judgement about me and expect it to be right, without knowing that it might not be?”

Turns out that it wasn’t necessarily that.

And whether this keeps me out of unneeded conflicts over the subject in the future remains to be seen, but it was definitely an eye-opener.

I’d still rather be overestimated than underestimated, but I’ll do my best to not assume that this is logical, and try to see that as personal preference instead.

*And the picture? It’s of me playing an evil prince at a larp, disguised as an old beggar lady. The kids tried to steal from me because they thought I was old and slow. So when they put their hands into my beggar’s cup to take the money, and I grabbed their hands, they were mighty surprised. In this case, it was fun to be underestimated, but then again, I was player a character. ;-)

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Director at The College of Extraordinary Experiences, Coach at McKinsey & Founding Partner at The Global Institute For Thought Leadership. Author of 31 books.