Work Friends

Melissa Winter

Chief of Staff to Michelle Obama

Melissa Winter was not supposed to end up in the White House. In fact, in the ‘80s she was an art history major with no aspirations to work in government at all. That was until her brother accidentally landed himself two Capitol Hill internships in one summer and Winter was pushed to join him, intended to take over one of the esteemed intern positions her mother had already paid living expenses for. From that summer on, Winter’s future looked completely different. She enjoyed public service work so much that she negotiated a new internship role the following summer, parlayed it into a paid opportunity, and when she graduated college, she moved from her native San Diego to D.C. the very next day.

However, it was after serving two offices early on in her career, with Congressman ​​Norman Mineta and Senator Joe Lieberman, that Winter found herself in the home of First Lady Michelle Obama, then the wife of a Chicago senator and presidential hopeful. The two clicked and Winter signed on to play an integral role on her team, working closely with her schedule and her family. It’s a responsibility Winter oversaw before, during, and after the Obama administration, and one she takes very seriously.

About 15 years after that first meeting, Winter continues to serve as the Chief of Staff to Mrs. Obama, but that’s not to say her role has remained the same. Instead, it’s in this very moment—now working outside of government guidelines for those in office—that she’s experiencing one of her most exciting chapters yet. Winter’s role has shifted from supporting those in the highest office to helping orchestrate a 33-city book tour for Mrs. Obama’s bestseller, Becoming, and working alongside Higher Ground Productions and the Obama foundation. The common thread throughout? Winter makes things run, often on a profound scale. And though her efforts are sometimes invisible to those who are only focused on the principles she stands behind, her ability to keep things operating smoothly—be it government offices or arenas full of book lovers—is nothing short of awe-inspiring.

"Public service has never been more important than it is right now...And more than ever, we have to bring our friends and family along so that people understand the connections."


The first summer before I interned in Capitol Hill I couldn't have told you anything about anything, other than the drinking age was 18 in Washington D.C. at the time and that sounded like fun. So with that, I felt I could take over the summer internship from my brother. I registered to vote, studied up on Congress, and when I arrived, I landed an internship for Congressman John Bryant from Texas. I had an incredible summer. I lived in a dorm at Georgetown University, made a bunch of new friends, and because of that experience, I realized I really loved public service and politics.

The next summer, I wrote to the Congressman’s office and said I wanted to come back but I wanted to have a paid role. I wrote to the program that I interned through and said I wanted to be an RA so I could have my housing covered at Georgetown. They all said yes, for some reason. I came back that second summer and it really solidified the path forward for me in public service.


One of the reasons I have been successful in my career is because I figured out early on what I was good at and what I enjoy. If I had tried to force myself into doing legislative work I don't think I would have had the same level of competency. I loved being a scheduler. It was one of my favorite jobs to this day. I loved letting Senator Lieberman know when he needed to be in a committee hearing or telling Congressman Mineta he needed to get to the floor for a vote. The rush of juggling multiple things at once—keeping the trains running—was what kept me totally engaged and happy in the job and ultimately successful.


After President Obama won, I went into the White House as Mrs. Obama's Deputy Chief of Staff. Again, I knew that I did not want to be doing policy work, I wanted to run things: being behind the scenes and making sure that operations ran smoothly. First and foremost, I wanted to continue my work with the family, which also meant overseeing Mrs. Obama's scheduling, correspondence, and working closely with the social office. I understood the importance of her family time. We crammed everything that we needed her to do into her work days, but she was home when the girls got home from school. That was super important and that was a role that I took very seriously.

Then over time, my responsibilities increased and by the end of the administration in 2017, it was a given that I was just going to continue on with Mrs. Obama. I don't even remember us having a formal conversation, it just was understood that I was going to run her D.C. office and team.


In my professional life, I’ve basically had three bosses: Congressman Mineta, Senator Leibman, and Michelle Obama. And each one of them is an extraordinary individual. And what I learned from each of these principals was the value of public service and giving back. None of these people did what they were doing because they wanted to make a fortune. In fact, our politicians are woefully underpaid. 

While I may have come to D.C. initially because I wanted to have a fun summer as an intern, I learned so much from the people that I worked for and I resisted the urge of so many of my friends in college to be business majors just to make money. That was never a priority for me. I wanted to do good and give back. One of the things that I loved when I was an intern on Capitol Hill was just interacting with all kinds of different people and giving tours and talking to constituents and seeing what was on people's minds, and that is what kept me interested and engaged in politics for the next 20 plus years.


When I was working for Senator Lieberman, I could have never anticipated he would be picked to run for Vice President along with Al Gore and then for me to be on the road with him from August 2000 until the election in November. I was part of a historic election that didn't end up the way we had hoped. But with a little hindsight, I now see that, while Al Gore and Joe Lieberman understood what was at stake, they handled it like professional politicians and gentlemen. The world moved on. And living through that was, in many ways, a precursor to seeing what has happened in our current political system through a different, and disappointing, lens. 


Public service has never been more important than it is right now. If people have the ability and resources to be able to work at the state level for the legislature, intern for a member of Congress, work on a presidential campaign, or do whatever they can do to understand and immerse themselves in the system, it’s so important. And more than ever, we have to bring our friends and family along so that people understand the connections. For example, how many people know that the United States Senate confirms Supreme Court justices? And, do they understand that if you don't vote in every election, then you might not be voting for the Senator who reflects your values? And then those senators can confirm Supreme Court justices who make rulings that perhaps devastate you. 


I don't necessarily want to stand out with my clothes, but I try to be prepared to go anywhere at a moment's notice. I don’t want to ever worry that my wardrobe might in some way reflect poorly on my boss. My job is always to be the person behind the person. And because I've traveled so much with Mrs. Obama, I look for clothes that make me feel comfortable, clothes that aren't forcing me to constantly “correct” something. I want to have the buttons be in the right place, I want there to be pockets in absolutely everything, and I want things pinched at the waist, but generous up top. Because you know how you feel when you know you look good. You're better at everything, you're more efficient, you're happier, and you're moving through your day in a different way than you are if you're fidgeting with your clothes.


One of the most interesting parts of this job, which I never predicted, is the variety of things that I'm learning and getting access to. Not only did Mrs. Obama write this blockbuster book after leaving the White House, Becoming, and I got to be a part of that process, but she also has a production company where there are podcasts, films, and documentaries, as well as the Obama foundation. The diversity of projects on my plate on any given day has kept me so interested that I haven't cast about to see if there's something else I want to do because there's always something new coming in. I feel like the job that I'm in now is the reward for all of the long hours and hard work and low pay of the early years in government. I feel like this is what I've been working towards.

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Find Melissa on Instagram.