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Senior Advisor to the President Valerie Jarrett (pictured) chatted with Esquire Magazine for their “What I’ve Learned” feature series, and her varied musings on her relationship with the President, why she doesn’t keep ice cream in her home, as well as why she switched paths along her professional journey provide a delightful lens in to an accomplished woman’s life.

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While many may know that Jarrett was tapped to become an advisor to President almost as soon as he became the President-Elect in 2008, some may not know exactly how far back Jarrett and the Obamas actually go.

Jarrett actually met the Obamas in 1991, after she interviewed and immediately offered Michelle, who was Barack‘s fiancee at the time, a position at the mayor’s office. Afterward, the young couple reportedly went to dinner with Jarrett, where Jarrett was introduced to Barack.

Their relationship would gel quickly, with Jarrett “introduc[ing] them to a wealthier and better-connected Chicago than their own.” And when Jarrett would leave then-Mayor Richard Daley‘s office to go to Chicago’s Department of Planning and Development, she would take Michelle with her.

And the rest is history.

In her interview with Esquire, the former CEO of the Habitat Company openly talks about the difference between Michelle and Barack, saying, “The President is the kind of person who, the day before the final exam, would open the book, read it, and get an A. The First Lady is the kind of person who, the first day of class when they were discussing dissertations, would plot out how to finish hers.”

Jarrett also talks about her comfort with going from boss to “employee”:

“I spent the first 18 years of our relationship being the older mentor. I liked our relationship like that. It worked for me. One of the reasons it was so easy to have my mentee become my boss is because I respect him.

And if you are wondering whether Jarrett always knew that Mr. Obama would be something special, she says about his Senate run, “I did question the President back when he decided to run for the U.S. Senate. I wasn’t sure it was the right time for him. That has generated periodic humor at my expense.”


If you had asked me on the night when I first met him, could that be possible, I probably would’ve said yes, but it would’ve been a fantasy. But to then live it and share it with my daughter, who thinks it’s perfectly normal to have your mom’s friend become president of the United States….”

Jarrett also sheds some light on how her earlier path as a high-powered lawyer made her “miserable”:

I was the first person in my family to become a lawyer. I was working on the seventy-ninth floor of the Sears Tower. I had a great office overlooking the sailboats on Lake Michigan. But I was miserable. A friend advised me to think about city government. I was hesitant—I was on my path and, miserable as I might be, it was my path.

“But Harold Washington had become the first black mayor of Chicago, and I made the move. I got a cubicle … with a window facing an alley. That was a little jarring. But as soon as I stepped in that cubicle, I felt This is where I belong. I was working with people who shared a common passion in their love for the city. I thought, Hey, I can get used to this cubicle.”

And about that ice cream, “I try not to keep any ice cream in the house because I can go through a pint pretty fast.”

Read the rest of Jarrett’s compelling thoughts here.

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