Insight: Overestimating and underestimating

by Calvin on October 23, 2014

I just realized: I have shame around overestimating myself. If I overestimate myself and my capabilities, especially in the way that I present myself to the world, and I get caught, then that’s really really shameful. I’m a fraud, I’m an egomaniac, I’m self-absorbed, I’m a hot-air balloon, and whatnot.

Somehow underestimating myself dosen’t carry that same level of shame. Underestimating myself is noble, humble, righteous, virtuous, admirable.

But in reality, underestimating myself is just as bad as overestimating.

By underestimating myself, I hold myself back from doing the things I’m capable of, which ends up robbing other people of the gifts and talents I have to offer.

And underestimating is possibly even worse than overestimating: Since we tend to gravitate towards our self-image, perhaps having a somewhat inflated self-image could possibly help us get there, and be even better positioned to share even greater gifts.

If you’re trying to stay precisely on a given line, but straying to one side of the line is deadly, and straying to the other side is relatively harmless, or even “noble”, guess which side you’re going to err on?

If both are equally bad, there’s a much greater chance of you staying on that line.

That’s how I want to think about underestimating and overestimating myself.

If you’re not willing to overestimate yourself sometimes, you’re bound to underestimate yourself all of the time.


I thought of starting a new blog series titled “Ramblings of a Man Desperately Trying to Distract Himself from Stepping Into His Purpose”.


Because that seems to be what I’m doing.

I know my purpose involves being on stage somehow. I know I’m here to teach and entertain. I’m here to share spiritual truths from somewhere deep within my soul, I’m here to make people laugh, I’m here to play music.

And yet, what am I doing?

I write software. I go to other people’s comedy shows. I learn how to make cocktails. I spend hours and hours cooking elaborate meals for friends. And I’m getting a New York driver license.

The driver license in particular is interesting.

I told Sam, one of the handymen in my building, that I was studying for my written test. He looked at me like I was an idiot. “Why are you studying? Are you crazy?” Uhm, no, didn’t think I was at least. “I just went and took the test, figured I would know enough already without studying.”

Good point. I studied. I spent at least 5 or 6 hours reading through the driver’s manual and the motorcycle manual to make sure I knew all the specific US rules.

What did I get for my effort?

Sure, I aced the test. I got 40 correct answers out of 40 possible (I had to take two 20-question test,s one for car and one for motorcycle). The guy at the DMV said it didn’t happen too often.

But a total of 28 correct answers, 14 per test, had been sufficient. I overshot by over 40%. I’m pretty sure having aced my written test will do nothing whatsoever for my driving experience going forward. I won’t get cheaper cars, cheaper insurance, cheaper tickets, I won’t be allowed to drive faster or bend the rules any more.

I will get absolutely nothing for my effort, other than the knowledge that, yes, I’m capable of studying for a really easy test and ace it.

And that, my friends, is how you stay busy with meaningless stuff so you can avoid stepping into your purpose.

Stay tuned for the next installment…