Steve Jobs, Kim Kardashian, and Trying

If you haven’t read Mona Simpson’s eulogy for her brother Steve Jobs that was published in the New York Times last week, you really need to. Besides being an incredible tribute to her brother, it’s also an amazing piece of writing in its own right. One part of the piece that particularly struck me is when Simpson writes about how hard her brother worked and why:

He was never embarrassed about working hard, even if the results were failures. If someone as smart as Steve wasn’t ashamed to admit trying, maybe I didn’t have to be.

The world is a cynical place. At least in 2011 and in America, we expect most things to fail. The economy stinks and most people expect it to get worse before it gets better. The public expects Congress to cause more problems than they solve. We wait for celebrity marriages to fail and our local sports teams to lose in heartbreaking fashion. Lots of people, not just the Occupy Wall Street crowd think that big financial institutions are basically stealing money from regular people. And being cynical doesn’t mean you’re wrong as the Kim Kardashian “wedding” and the near daily use of the filibuster both show equally well.

But being cynical often leads people and societies to stop caring and stop trying. Why paint over that graffiti when someone is just going to come along and re-tag it next week? Why run for local elected office if the big political machines will stop any progress anyway? Why try to start a new business when most fail? Better to leave that to someone else and focus on something easy, simple, or low-stakes.

We’re too often cynical/worried/afraid to try and especially to admit to ourselves and others that we are trying. Because when you admit that you are trying, when you are obviously working so hard, is to put yourself out there as caring, hopeful, and vulnerable. If you are really trying at something, whether it is creating a mass-market personal computer or working as a teacher in a high-need neighborhood of Philadelphia, you are taking a risk that you might fail. And it's no great insight to say that failing sucks and most of us would rather avoid it.

But in such a cynical world, more than ever we need people to try and not be ashamed to admit how hard they are working and how much they care. People like Jane Golden who not only wasn’t afraid to paint over graffiti, but created a whole organization to paints works of art over it. People like Bill Ferguson, who ran for State Senate in Maryland with no political experience because he knew that government needs more people who care about urban education. And yeah, people like Steve Jobs who not only started Apple, but came back to lead it again when most people were predicting it would quickly be out of business. Not only did he keep the company out of bankruptcy, but he led the creation of the iPod, iPhone, and iPad, revolutionizing whole industries.       

Part of what I love about both Teach For America and KIPP comes from this simple idea that it’s ok to try. The problems confronting our students individually and urban education collectively are huge. It would be easy to see these challenges as unsolvable or to say that we can only try to tackle them after something else happens first. But ignoring or waiting means nothing will ever get better. And that's just not ok. I’m really proud to work with people who work so hard and aren’t afraid to try to make a better world for our students.