THE BLOG
08/04/2011 06:59 am ET Updated Oct 04, 2011

Obama and Me

We're pretty much the same age, similarly overeducated and both raised in predominantly white neighborhoods (but I'd trade Oahu for Hamden, Connecticut, any day of the week). We're both recovering nerds and his meteoric rise was like rocket fuel to my own love life when I was single.

We're both corny, old-fashioned patriots and pretty hawkish for Democrats. I wrote a play about the Tuskegee Airmen that continues to tour around the country and that centers around his historic election. Though I haven't met him since I gave $100 to one of his senatorial fundraisers, the Ivy Buppoisie being only but so big we have more than a few friends in common. I'd like to think that we could be friends.

That doesn't stop me, however, from vociferously criticizing some of the decisions he and his administration have made and their negotiating tactics. I haven't gone down the road of Professor Cornell West but I am concerned, dismayed and depressed by several of the president's positions since taking office.

And hopeful.

It is extremely difficult judging someone whom you feel is so much like yourself. It can't help but make you reflect on your own psyche, your own imperfections. I had one of the most insightful conversations of my life with Stanford's Dean of the School of Education Claude Steele about how difficult it is for black men to pivot from ambitious striver to Head-Negro-In-Charge. The very skills we had to develop to navigate the treacherous waters of white underestimation: the conciliation, the perpetually even temper, the disarming charm are not always the most effective if we ever actually make it to the top of the heap.

The pivot to becoming the "decider," as the president's predecessor put it, the one who no longer has to care so much what everyone below him thinks, is a terrifically hard one to make. It takes time to understand that you no longer have to react to a received reality but with will and constancy you can create a new one.

It's like moving from dancer to DJ.

Our president is clearly one of the brightest to ever hold office. His political team refreshingly, clinically ruthless for Democrats. Despite the many missteps of this first term I am hopeful that in a second, freed from the need to ever again campaign, President Obama will finally help usher in change that we can believe in.