Wednesday, February 12, 2014

Crisis of confidence?

I have been told I seem like a generally composed and put together individual.  However, what you might not know is I have this bad habit of absolutely hopelessly breaking down into a teary eyed, whiny, self loathing, pathetic mess the day before I start anything big and new.  (Attractive, yes, I know.)  Unfortunately, try as I might to resist it, I have always been this way.  It has proven to be a time honoured tradition across time and space.  It happened the night before I left for college, the eve of of my first internship at Goldman Sachs, the day before I started in Equity Derivatives, the night before my first day at General Assembly, the day before I moved to Hong Kong...  I think you get the picture.  Any efforts to prevent it have proven futile and I have found I have no other choice other than to simply brace myself for the breakdown.

With that as my track record, I suppose I can’t be surprised when, most recently, it happened the day before I started my new job in the space of angel investing. Per usual, and especially due to the fact that I have exactly zero experience in this field, I felt hopelessly terrified that I might not be able to contribute in a way that would be useful to my colleague, our investors, or our investments. Ah yes, yet another venture off into the unknown.  It certainly didn’t help that all of my household appliances had broken concurrently, and my inability to overcome the extreme inconvenience of getting them all fixed was making me feel like a totally incompetent adult human being.  My mind and heart were overflowing with fear - both rational and irrational.

Many people have tried to offer me advice on how to avoid these situations, but most conventional wisdom just makes it worse. In fact, I fucking hate it when people just say, “Just be confident.”  “Just be bold and act like you know what you’re doing even if you don't." "Fake it ’til you make it.”   Well, sorry but, I could absolutely never do that because I don’t think I know everything and I am simply not capable of faking it.  I’ve always been one of those people who readily admits when I don’t know, don’t have all the information, or don’t have a strong opinion.  Except for very special circumstances (like I know you’re full of shit, or I’ve had a tad too much to drink), I don’t like to argue just for argument’s sake.  Perhaps part of me assumes that other people are the same way, so if someone is willing to push vehemently for one side of the argument, they must know more than me in order to have so much conviction.

This certainly doesn’t mean I’m a wallflower when it comes to debates or confrontation.  If I do truly know what I am talking about, sense that I know more than the other person, or that they’re running on the fumes of false confidence, there is no stopping me.  I’ll only push hard for things I genuinely believe, and I’m not one who gives up easily on things I really care about.  This means that if I have genuine confidence in myself and what I’m doing, I can go very far.  Unfortunately, this only serves to fuel my crippling self doubt because I am acutely aware of the fact that in many ways, I am the only thing holding me back.  If I could “just be confident”, I would be completely fine.  God dammit, I suck.

Settling for nothing less than authentic confidence may feel respectable, but the reality is that this “all or nothing” view of conviction just doesn’t work.  At the end of the day, I will never have all the information.  In many cases, I will never have enough to feel comfortable having a strong opinion.  Now, it’s actually my job to have an opinion without all the necessary information.  Part of investing in early stage start ups (part of starting anything new, frankly) is to have a strong view, move confidently in that direction, and do whatever you need to do to validate it.  The key is not being blindly bold, but being sure in not knowing enough, not knowing everything — embracing and owning the uncertainty.  It’s not false confidence because I know and readily admit there is plenty I don’t know, but that doesn’t mean I can’t take action.  If every opinion is simply a hypothesis, and then the only respectable thing to do is test it.

And, as I have discovered, there’s no better way to test things than by just shutting up and getting started.  I may have my semi-regular break downs, but as soon as I make it through to the other side, I feel better about things.  I’m one week in to the new job, I’ve stopped questioning, stopped worrying, started learning new things, started asking questions, started thinking of how things could be different or better…. and in the process, my confidence is growing (I think.)  Actively participating means there’s no more room for the self doubt or fear of embarrassment or disappointment.  The more things I do, the more lists I make, the more emails I write, the more people I meet, the more problems I start to solve, the less I wonder what I can do and the more I show myself what I can do.

So, of course, I have no answers, nor do I have any semblance of a cure for my habitual crises of confidence.  Maybe I don’t want a cure.  However, I feel good about the fact that once I get the ball rolling, I don’t need to fake it.