W hen I graduated college, I got hired at EMILY’s List, which helps elect pro-choice Democratic women. I went to Oklahoma to work for this candidate who was running in a primary. I worked on the campaign for three months, and she lost. I was up all night, and I had booked a flight home early the next day out of Tulsa. It was my 25th birthday.

On the way to the airport, I hit a raccoon. Another mile or two down the road, there’s smoke pouring out of the car and I have to pull over. It’s early. I don’t know anybody. How am I going to get to Tulsa? Can I call this candidate who just lost an election and ask her to help me? I start to cry.

I remember stopping and being like, No one is going to get you out of this mess. You are going to have to figure out how to deal. So I pick up my cellphone and call her, and she sends a friend to pick me up, and I make it back just in time to celebrate my birthday with my family. Whenever I face any challenge, I think back to that moment in the car: You need to get it together.

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I was put in a gifted track in elementary school. We were learning Mandarin, and we had pen pals overseas. The kids who were not in the gifted track? They took a sixth-grade field trip to the state park. It occurred to me that it was the kids who weren’t on the gifted track who needed a fuller experience. I said “Why?” to our principal. He was a big dude. He bent down and said, “Look, they do get stuff.” I didn’t buy it. He said, “Well, we can disagree about that.”

Years later, I was teaching history at Englewood High School. Arne Duncan, who was in charge of CPS then, came over with the aldermen in tow to tell us that they were going to close the school because of test scores. I thought that they should’ve been in there saying, “We’re going to pump this place full of resources. We’re going to figure out how to meet the needs of the students.” My principal back in elementary school had been gracious enough to engage with me. They did not engage.

I began to question: Was I an agent for change, or was I helping perpetuate the system? That’s how I find myself at the teachers' union.

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I ’m a first-generation college student from a small village in England. I received a government grant because I came from a low-income family. When I got to the University of Manchester, I had not experienced the world the way many of my peers had, many of whom had gone to private schools and traveled to India and Thailand. It was eye opening.

My senior year, I decided to take a research trip to New York. That was the first time I got on a plane by myself. My parents were horrified. My adviser had written me a check in case I ran out of money. I was trying not to cash it. There was this kiosk that sold bagels, and I would get a bagel with a brick of cream cheese in it and just eat that all day. I saw lots of cinema, went to lots of bookstores. I did research at the New York Public Library, not knowing that one day I would work there as director of exhibitions.

I learned that I could do literally anything. I could get myself on a plane and get off the other end, travel freely and learn and meet people. From that point forward, the world was my oyster. And I returned that check.

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W hen I was a freshman in college, I went to a national leadership conference in upstate Michigan. As part of that, we were basically dropped into sand dunes with a compass and told to navigate our way to another place, where there would be food and sleeping bags for the night. Then we had to navigate our way back.

At the first stop, there was food, but it was rice, and it was uncooked. So we had to build a fire and figure out how to cook the food. It was getting very late, and we were not at the campsite yet, walking in chest-high water and carrying lanterns over our heads because the beach had eroded. Not everybody knew how to swim.

I had no intrinsic deep fear. It felt like an adventure to me. That was the first time I recognized that I had something different in terms of my ability to navigate through ambiguity, to calm people when they were worried.

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I was a sportswriter at Northwestern covering men’s tennis, football, and basketball at a time when women were not allowed in the locker room. I would stand outside and wait for everybody to do interviews inside, and then I would chase the players to their cars, hoping to get a word or two. My quotes were inevitably very short, because everybody had said it all inside.

I hoped to be one of the first women sportswriters in Chicago. When I left Northwestern, I became a producer at WIND radio, where at one point I delivered the morning sports report on Dave Baum’s show. I was the first woman to do it. And then Dave decided he wanted to do his own sports. I remember being totally crushed. After that I made the switch to news.

Now when I’m trying to get an interview, I try the front door, back door, side door, window. I’m like a terrier who has ahold of the politician’s pants leg. And maybe it’s all because I couldn’t get into those locker rooms.

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