Self-Deprecation vs. Accurate Self-Assessment

I’ve been thinking a lot lately about the idea of being self-deprecating. I often enjoy being around people who are modest, self-deprecating types. I often try to be so myself. As Paul Ingraham puts it, quintessentially:

“Candid self-deprecation is very disarming. I’m terrible at it, but I do my best.”

Self-deprecation is often a person’s way of saying they care more about making you feel comfortable than about showing off. Much of the time, self-deprecating types tend to be good people, and not too full of themselves.

I’m also enthusiastic about the idea of accurate self-assessment, though. Sometimes these two proclivities come into conflict. Too much self-deprecation starts to look disingenuous or obnoxious (the concert pianist who describes themselves as “not very good”).

Take an example: I tend to think that I’m smarter than most people*. This presents a problem: I like making people feel at ease, I like being self-deprecating, and all of that. But I also think honesty, both with yourself and others, is important. I think people who are good at thinking, writing, baking, candlestick-making, etc, should say so.

I used to identify much more with that line from Ten Things I Hate About You: “So, you’re disappointing from the start, and you’re covered, right?” Set expectations low and you can only exceed them. Then if someone gets in a relationship with you, you can only end up being better than they expect. Whereas if you oversell yourself, you might disappoint someone. I’m a skeptic, though. Eventually, I picked up on the fact that there’s a flip side: if you’re a good person to be in a relationship with, and someone decides not to be in one with you because you represent yourself in a relentlessly self-deprecating way, it’s your fault that person missed out on the experience of you.

The best thing to do is, well, be honest and try to be accurate, I think. Old habits die hard, though. I can’t help but be uncomfortable being explicit about the fact that if I’m honest, I think I’m smart, decently witty, good at making people feel comfortable, far above average at communicating (though I still have much to learn), and can kick your ass at word finds. If I’m honest, a part of the reason I wanted to start a blog is because I think I have important things to say. Saying that out loud, though, remains uncomfortable.

I like figuring this out, though. I like that part of the justification for it (underselling means people might miss out on you) requires me to think about the fact that I am something someone could reasonably be described as “missing out on”. So that’s something.

*I’ve elected to leave out the story of the long period between my realizing that I thought this and deciding I was probably right for the sake of brevity. However, for the sake of assuaging my nervousness about being thought of as arrogant, I’ve elected to include the previous sentence explaining that there was one.