There’s a lot of personality characteristics that one observes common among technical founders — driven, passion, commitment, and perhaps above all, and underlying desire to be perceived as the smartest guy(gal) in the room. This isn’t just common in the startup world by any means. I’d argue is even more common in information security — go to any conference and you’ll get your fill of this ego-driven behavior, as if all of the skeptism that makes a person great at evaluating the security of system must be complemented by the need to be perceived as not just supremely legitimate but “elite”, with amazing technical chops and all-encompassing know-how.
So how does an outsider that doesn’t fit the traditional mold (e.g., women) start out in this space? You’re surrounded by “rockstars” who seemingly already know everything and if you don’t, you are just a wannabe, probably regarded with mild suspicion or curiosity, at best. You don’t want to embarrass yourself or be called out for your ignorance, but you have to start somewhere, and you have to be able to ask for help.
We all have a tendency to play to our strengths. As a child I had some natural talents — I was a shy, intellectual kid, that kind that did well in school, especially in analytic subjects, like math or science. I was bad at anything to do with my body — I had terrible hand/eye coordination, and I didn’t feel particularly creative. So, I stayed away from organized sports, dancing, art or anything that I felt would make me look foolish, and instead would gravitate toward extracurricular activities that would I would naturally fit into, things that would make me shine — e.g., math clubs or foreign languages.
I suspect this is the natural order of things. We are encouraged in our talents, by our parents and even by our own tendencies — none of us want to look bad. None of us wants to be the worst at anything. And perhaps this is healthy in a way, it’s part of what builds our self-esteem, getting affirmation that when we do well we will be valued for it. But I think by limiting ourselves we lose out not just on experience, but on the lessons those experiences bring. And one important lesson is “Don’t be afraid to be the worst at something.”
Think of something beautiful or amazing you saw and thought… “I wish I could learn how to do that.” I’d wager it’s almost immediately followed by the silent, maybe even thoughtless corollary: “…but I could never try because [I’m too old|I’m too uncoordinated|I’m too uncreative|I’m not smart enough]. I would embarass myself.”
The turning point for me was when I had the self awareness that this essential fear was holding me back. “But really, why is embarrassment so bad? Even if you’re not good at something, if you can get any benefit out of it, why should that stop you?”
If I never had this realization, I would never have left my well-paying job to do a startup. I would have had a totally different life. I may have never even left my hometown or become a programmer. But like most realizations, it’s easy to say and acknowledge, but even harder to internalize and adopt into your life.
So how do you learn how to internalize this? You practice being the worst. You try things you want to try, knowing you’ll probably be bad at them, and you inevitably fail.
I started small, tacking all of the awkwardness I felt about my body. I tried anything I had ever wanted to try but felt afraid to because I would look stupid. I tried aerobic dance classes where I was so awful that the teacher felt sorry for me when I couldn’t follow any of the moves, stopping the entire class at one point to ask me “do you need help?” I took up a musical instrument where my hands shook for many months not just in recitals but in my actual lessons, when my mind would blank out under my teacher’s pitiful stare as I tried to just make it through a 2 minute piece I was learning. I failed over and over again. Yet, I ended up finding and loving some of the best hobbies that I treasure and give my life meaning today. Kyudo. Piano.
Learning music as an adult is a great way to practice being the worst.You are surrounded by kids who are way more talented than you, who have years of experience already, and seem to pick up skills immediately, where you have to struggle and struggle. When you have stood in front of an audience and totally bombed a recital and “humiliated” yourself, you realize there really aren’t the consequences you thought there were. Ok, so you have been The Worst at something, and guess what? You learned that life went on.
Practice being the worst at something. It’s even better as an adult because you have that full adult self-awareness. You have to overcome all of your learned inhibitions. You fail and then you learn how to get back up. You reinforce that getting back up is always possible.
You learn how to walk into a room of technical superstars and being afraid about fitting in or looking stupid isn’t really that large in the scheme of things — you have already been The Worst. You learn that the fear of risking everything on a startup really isn’t that scary — even if you fail, you learn from your failures, and you try again.
But best of all, you learn that with enough time and practice, you will inevitably no longer be the worst. You will get better. You can even be the best.
