What was the best advice you’ve ever received, who gave it, and when?
My second-grade teacher told me “you’re going to fail again and again, and the real test is going to be how quickly you get back on your feet.” At the time it was kind of a bummer. I mean, no seven-year-old wants to hear that there’s a lot of failure in store, but it was good advice. I had done absolutely horribly on an exam. I wanted to get out to recess, and I just put anything down I could think of because I was so eager to get outside. Not surprisingly, I failed miserably. But I didn’t put two and two together. At that age, you don’t always act particularly rationally, and I was downcast afterwards. The teacher was like, life is going to be full of failures, and the question is what are you going to do with them? At that point, I managed to link cause and effect, and I made the deep and penetrating realization that I was so eager to get out to recess that I had blown the exam. And maybe, therefore, I should take a little bit more time.
What’s the best way to get powerful people to listen to you? How do you say ‘no’ to, or that you disagree with, someone like the president?
It’s very hard. One of the great difficulties those in power have is hearing constructive criticism, because everyone around them wants to fill their ears with compliments. A very good leader will reward constructive criticism and will seek it out. The average leader doesn’t want to hear it; in fact, none of us do. When you know the powerful person very well, since, say, you were in graduate school together, then you can quietly, in the presence of only that person, be a truth teller and damn the consequences. The two keys are trust and privacy.
What’s the one thing people don’t really understand about working inside the White House?
They don’t understand how difficult it is to drink from a fire hose. Everyone assumes that a president or cabinet officer has time in the day to focus on what is important by sifting through the information. But knowing what’s important and making those distinctions is very difficult when everything is coming at you intensely. Secondly, finding time to think and strategize is exceedingly hard, because if you’re not careful, you’re constantly reacting. Also, people who watch ‘The West Wing’ are under the misperception that there are a lot of clever one-liners, and great bonhomie, in the White House. That’s usually not the case. People are under great pressure. The clever one-liners are exceedingly rare, and not everybody loves each other.
How difficult was it for you to grow up as a shorter man? How did you compensate?
It wasn’t particularly difficult until my teenage years, when every blemish and pimple becomes a catastrophe. I didn’t even realize that I was particularly short until some of the girls didn’t want to go out with me. Then I thought to myself, “Is it my personality? I don’t think that’s it. What is it exactly?” Some of my close friends explained that it might be because I was unusually short. Also, in my earlier years, starting at about the age of five, I was subjected to a lot of bullying, but that’s not unusual. I overcame that by making alliances with older boys who would intimidate the bullies.
One of your protectors became a Freedom Rider and was murdered by the Klan. How did that affect you?
I was so appalled and upset at the time that I don’t think I fully realized until years later that the murder of one of my childhood protectors by the real bullies – white supremacists, including officials in Neshoba County, Mississippi – ignited in me a passion to protect people who were vulnerable. To protect them from all kinds of bullies, including economic ones. We’ve gotten to a point in the evolution of our economy and politics where very few protections are left between families and the potentially devastating economic environment. There aren’t the layers, the cushions that used to exist between the harshness of the economy and everyday life for most people. That means that many people are far more vulnerable than they have been at any time since the great crash of 1929.
What’s it like to run for office? When you ran for governor of Massachusetts, did it make you more or less sympathetic with politicians?
It was much harder than I expected. In fact, it was horrendous. I hated every minute of it. I discovered that I am constitutionally incapable of kissing ass. I just hate to ask people for money. I hate to pretend I like somebody when I don’t. I have no natural political skills, and it was a terrible mistake for me to run. As it was, I didn’t do so badly. We just didn’t do the money side of it well enough. My respect for politicians, as a result of that, has increased substantially. Somebody like Bill Clinton loved to be out there shaking hands. In fact, if he didn’t get enough handshaking in a given day, he was sort of depressed. I’m just the opposite. I found it grueling and exhausting. And fundraisers were nightmares.
What advice would you give to the younger you?
I’d say if you want to have any impact on the world at all, you’re going to have to have a very thick skin and you might as well develop that as early as possible. I’d probably say, leave the Clinton administration after the first term, which I did, and I’d say, smart move Bob! Even absent Monica Lewinsky, because personally it was a smart move. I’d say to myself that your proudest achievement and most lasting legacy will be through your boys.
What role does vanity play in a man’s life?
Men are competitive and many need a kind of recognizable achievement, but without adequate self-reflection that can lead to some very unhappy spots, because not everybody can be successful at everything. And not everyone is going to be at the top of the pecking order. If your sense of self worth turns on external achievements, then you’re setting yourself up for some real sadness in life.
There’s an amazing line in the movie, ‘Inequality for All,’ where you speculate about whether or not you’re a failure. Even with all your achievements, do you really feel that way?
Well, occasionally I do, particularly with the issue that I’ve spent a lot of my life working on, which is the widening of the inequality of wealth and opportunity. The country is worse off today then it was 35 years ago when I began writing and researching and making a ruckus about all of this. I don’t dwell on a sense of failure, but occasionally I do worry that much of what I have invested my life’s work in has really become worse rather than better.
Does it still drive you to try to fix that?
Yeah, I am still driven to do something about it. On the one hand, there’s probably an important distinction to be drawn about being passionate about something. And on the other hand, becoming so personally ensnared that if the issue gets worse or is not resolved in some satisfactory way, then you take it personally. I try not to fall into the later trap. It would be the height of hubris for a person to see himself or herself as a failure if an issue of complex social phenomenon or something like nuclear proliferation or climate change did not resolve itself. If I start feeling that way, I say to myself “Don’t be so grandiose.” You can fall prey, particularly in Washington, to a kind of messianic complex, in that you feel that you are far more powerful than you actually are.
How should a man handle getting old?
There are a lot of superficial answers about staying in shape and enjoying the life you have and all that crap, but I don’t think there’s any simple answer. For years, I refused to acknowledge that I was getting old. I teach people, most of whom are in the ages of 18 and 25, and I fall into the trap of thinking I’m between 18 and 25. I go out to lunch with my students and we tell jokes and we talk about all sorts of things. And then I get up from the table and I sometimes catch a glimpse of my students and me leaving the restaurant – in a window and for a fraction of a second I ask myself, who’s that little old man? It’s just shocking. We have the beginnings of a gigantic baby boom entering into old age – 76 million people were born between 1946 and 1964 and the early boomers are all now having to come to terms with aging. With that large of a population facing something as profound as this, you would expect we would have some better answers and we don’t. We’re in the dark ages.
What’s the one thing every man should know about money?
Not obsessing about it is probably the most important thing. My personal financial philosophy has been to buy high and sell low. So I never give financial advice. But having a good life doesn’t require gobs of money. People get deluded into thinking it does. Or thinking that financial worth is the same as moral worth, and nothing could be further from the truth.
‘Inequality for All‘ is out in theaters now.