Startup general interest

On cynicism and admitting when you don’t know

By January 13, 2014 6 Comments

A long time ago someone shared this Roy H Williams quote with me (although I didn’t know it was him until now when Google helped me out):

A smart man makes a mistake, learns from it, and never makes that mistake again. But a wise man finds a smart man and learns from him how to avoid the mistake altogether.

I thought that was pretty smart and have tried to live by it ever since. One of those ways is to hoover up ‘lessons learned’ posts, so when I saw Ben Milne, CEO and founder of Dwolla had written 2013. Hard Lessons Learned I clicked straight through.

The first thing to say is respect to Ben for a post that’s beautifully written, humble and insightful. It’s long but it’s great, and captivating enough to get you through to the end. I’m going to pick out two of his lessons here, but I heartily recommend you click through yourself and read the original (I’ve linked to it twice to make it easy for you).

The first lesson is on cynicism:


The moment your view is too cynical to see what’s good, you’re nothing but a paperweight that processes food and drink to simply deposit it in holes along life’s depressing way.

Cynicism is rapidly becoming my number one pet hate. It’s easy to be cynical and it’s hard to do stuff. Many people adopt cynicism as an intellectual cover for their inactivity, and that sucks. It sucks for the people on the whip end of cynical comments, but it also sucks for the cynic who, as Ben says is in danger of becoming an empty vessel. There are times when plans are very unrealistic and a degree of cynicism is useful, and as a venture investor I see my fair share of those times, but the key is to combine an awareness with what won’t work with what is good and will work.

The second lesson is on having the courage to ‘fess up in the face of ignorance:


One of my favorite questions in this life is and will likely forever be “what does ______ mean”. You see, I don’t know what every word means and I constantly ask people what something means if they use a word I don’t understand. That or I file it for later.

Someone not too long ago informed me that I had a “rather nihilistic” view of identity on the internet. I had to look up nihilist to understand his context. So what.

The world is changing so fast these days that the speed with which you learn new things is far more important than the body of knowledge you’ve already accumulated. When someone says something that you don’t understand that’s a learning opportunity. Not taking it will hurt you in the short term because you will struggle to get the most out of the situation you are in, and in the long term because you will face the rest of your life a little less smart than you needed to be.

That’s easy to say, but hard to put into practice, I know because for the last six months or so I’ve been pushing myself not to let anything I don’t understand slide past me. I’m supposed to be a smart guy, and admitting I don’t know something when it might be an obvious thing that I really should know is sometimes tough. I’ve come to understand that it’s a confidence thing. If I’m confident in myself and in what other people think of me then asking a question that might be a dumb question isn’t that scary a proposition. I’ll come through it in the short term, and so long as most of my questions are smart then I’ll be good over the long term too. Moreover, sometimes you end up looking dumb when you don’t ask.