A few years ago I was fortunate enough to be in the same room with the chairman of the Washington Post. Don Graham was at an event put together by “The Academy of Achievement,” attended by students from NYU and Harvard who had earned a fellowship in social entrepreneurship.
Don got to the podium and spoke about the history of the Washington Post and its plans to confront the digital threat. It’s 2010. I remember not liking his approach to tech and thinking that he really doesn’t know what he’s talking about. Others in the room are more receptive and ask him friendly questions. I wait my turn and ask him a question that challenges many of his assumptions about his approach to the web.
At the end of his speech, he stops while walking out the door, and, in full view of everyone, hands me his card then tells me to contact him. I thank him, and for the rest of the event friends congratulate me and ask what I will do with his email. I laugh it off and tell them that I don’t have any plans. “A job at The Washington Post is not something I want.” I never messaged him.
I’ve made a lot of mistakes since 2010. It took me far too many years to realize how many levels of a miss this was. Don is revered for a reason. His staff loves him. Mark Zuckerberg is friends with him. He ceded control of his legacy this year because he believes the mission of the Washington Post is far greater than his own ego.
I bring this story up because it’s a mistake I often reflect on and try to learn from. Knowing the difference between arrogance and confidence is one of the hardest things to do when you’re trying to make something new. If you lack confidence, you’ll submit to the will of people who are confident. If you’re full of arrogance, you’ll chronically overestimate your own ability.
Arrogance and confidence have many overlapping qualities. They both inevitably involve believing something that many others do not. They both require writing a check you know you can not yet cash.
It’s hard to control whether people see you as confident or arrogant because most of their opinion is based on whether you’ve recently been successful. A football coach who goes for it on a fourth down and gets it is seen as confident while the one who doesn’t get it is arrogant.
You can’t stop people from making hindsight fueled-judgements, but you can stop yourself from thinking in a particularly arrogant way.
The difference between confidence and arrogance has everything to do with empathy.
When you truly believe in a goal you believe that, with enough time, anyone can be convinced to share that goal with you. Everyone who walks around Earth is a potential convert.
When you’re arrogant, you believe only a certain type of person will be able to share your goal. This is an innocent seeming difference, but it ultimately becomes something that will warp your ability to make good decisions.
If your goal is at all bold or worth fighting for, you’ll soon find people who will reject your idea and want to burn you to the ground. Some of these people will deliver meaningful, thought-out criticism and some will dismiss you. If they dismiss your idea from a position of power, they’ll seem arrogant, and a knee-jerk reaction will be to mimic them.
Arrogance is a seductive feeling. When you dismiss someone in response to them dismissing your idea, you can feel as if you’ve taken back some power. This is temporary.
The problem with arrogance is that it makes your world smaller. The more you dismiss people as incapable of understanding your idea, the easier it becomes to do again. You create a category that they fit into, and when you assess a new person you turn attention to yourself. Instead of sitting down with someone to search for common ground, you sit down with them and try to rapidly figure out whether they have a predisposition to understand anything that you’re telling them.
Yes, your time is limited, and you can only connect with so many people, but if empathy is what guides you, it can make all the difference. The more you draw lines in the sand, the more others will do the same. You isolate yourself. And the more you’re alone, the more you’ll need to inflate your own ego and sense of ability to make up for the loss.
Arrogance crushes you. It makes you feel big in exchange for a network that is small and a mind that will never be good enough. Your desire to achieve your goal twists into a desire to prove others wrong.
When I was 22 years old I was confident enough to ask the Chairman of the Washington Post a derailing question. I was not confident enough to take the opportunity that he then literally handed to me.
My thought process was warped. Don was a dinosaur. Old Media. He gave a speech that reflected this. I thought of him in such a mediocre way that, when he gave me his card, all I could think was that he wants to hire me and this is something that won’t work. I didn’t think that he just wanted to talk. That his opinions are malleable. That he, like me, was just trying to figure out how to thrive in this crazy new era of news.
Who knows what would have happened if I followed up. We could have become BFFs. It could have been nothing. And this is the point. You don’t know. You never will know if you come in with those kind of expectations.
If your goal is huge, something that hasn’t been done before, your network of support will need to be unconventional. It will come from the places you least expect.
Open yourself to them.