President Obama on “Undercover Boss?”

I’ve been quite fortunate to be spending a few days in Chicago while reading Obama: From Promise to Power by David Mendell. Mendell is a Chicago Tribune reporter who followed Barack Obama during his run for the U.S. Senate in 2004.

Virtually anyone who’s been to Chicago knows that it’s a city made for walking. Its neighborhoods are rich in ethnic flavor and all but the wealthiest ones are microcosms of issues facing most Americans. As Mendell points out, Barack Obama knew the neighborhoods of Chicago when he was a community organizer and even during the time between graduating from Harvard Law and first running for political office.

As a community organizer, he kept his anonymity most of that time and essentially went wherever he wanted. He could talk with whomever he liked. He was a sponge; soaking up information from people struggling to pay rent, get the housing authority to remove asbestos, or put more vital resources into schools.

As I walked just a few of the streets of Chicago, I was saddened with the realization that this was something Barack Obama used to do and has not done for years. It may be that the poison fruit was the first campaign contribution he took which took him away from the streets and made him a child of Chicago’s Gold Coast, northern suburbs, and the fashionable part of Hyde Park. What he needed from Chicago then was money and votes. That’s a far cry from the tremendous thirst to learn about how the “common folks” lived.

There was a time when Barack Obama would spend days interacting with people trying to make a go of it on the south side of Chicago. Now he spends most of his days speaking with the likes of Tim Geithner and John Boehner.

A week without Geithner

On TV’s  “Undercover Boss,” the CEO of a company takes on a disguise to learn what life is like for the “ordinary employees” of his or her company. I cannot think of a more enriching experience for Barack Obama. Ever since his stirring speech at the Democratic National Convention in 2004, he has lived in a bubble. Every action he takes or doesn’t take has been thoroughly scrutinized.

Suppose that he could wear a convincing disguise and come back to his home state of Illinois for a week. He could meet with people in neighborhood restaurants. He could shoot a few hoops on a glass-strewn inner-city court. He could ride public transportation and see the joy, or lack thereof, on people’s faces. He could go to Walgreen’s or CVS and see how many people are scrounging for coupons. He could go to a pay day loan shop and see the anxiety and anticipation on customers’ faces. He could go to a casino and see people drink, smoke, and gamble away what might be meager savings.

He could travel the rural roads south and west of Chicago and talk to family farmers about everything from how new technology is increasing their yields to how they are threatened by big agribusiness. He could visit small towns to learn about how downtown businesses are trying to survive when a new Wal-Mart is about to be built close-by. He could go with a home-owner to a bank to talk about the mortgage that no longer can be paid.

It would be a week of reconnecting with the people who for so many years he was trying to directly help through community organizing including economic development. It would be looking at dollars and cents the way in which most families do; not the way that Tim Geithner or other top economic advisors do.

Back to DC

It would be too great a leap to say that Barack Obama would return to DC and like the “bosses of “undercover boss,” he would be so moved by the hardships that his constituents face that he would change his basic mode of governance. However, he would reconnect with the Barack Obama of earlier years and possibly feel a need to bring some advisors into the White House who don’t even have resumes. They just have life experience.

Not Likely to Happen

For any number of reasons, Barack Obama is not likely to be an undercover boss. But the need remains for him or any other leader to stay connected with the lives of those living ordinary lives or those truly in distress. Maybe he could sneak out of a fund-raiser early and show up unexpectedly at a hole-in-the-wall restaurant. Maybe he could go into a drug store to buy a pack of cigarettes, and then think better of it and buy a pack of Nicorette. Maybe he could ask a farmer if he could have dinner with the family.

As I walk the streets of Chicago and am constantly stimulated to think about the fiber of the community, I can’t get out of my mind that in that regard, I am more privileged than Barack Obama. He can’t take that walk, or at least he hasn’t been doing it. I just hope that somehow he can find time to reconnect with the people whose needs propelled him into politics, and do so without White House advisors and campaign handlers hovering over him. That’s my dream of my president.