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Michelle Obama's Next Act

Michelle Obama is quietly planning her next act


Michelle Obama, right, in October with Melissa Winter, a longtime aide who will serve as the first lady’s chief of staff as she embarks on her post-White House career. (Lawrence Jackson/The White House)

As Michelle Obama prepares to leave the White House, she’s been talking publicly about how eager she is to return to normal life. “I want to open my front door without discussing it with anyone — and just walk,” she told Oprah Winfrey in an interview last year.

She has also said she wants to sit in a yard, stroll through a big-box store and open a window in her house, all things she has not been able to do for eight years.

Yet a team is already laying the groundwork for what’s likely to be a somewhat busier post-White House schedule for a popular first lady who has signaled her eagerness to continue her advocacy work of recent years — and has proved to be a compelling voice in American politics.

After a long break, Obama plans to get to work with a small staff that will move into office space in Washington. The group will be led by Melissa Winter, the first lady’s longtime deputy chief of staff. A veteran Capitol Hill aide, Winter was the first lady’s first hire during her husband’s 2007 campaign.

“Mel has been by my side from Day One. There is truly no one I trust more completely to make order out of chaos and take an idea from inception to execution,” Obama said in an email. “For the past decade, she has been one of my most trusted advisors and dearest friends.”

The shadow of the commander in chief by its nature makes a first lady’s work smaller. But the post-presidency has been a chance for some former first ladies to find new missions, and Obama’s next moves will largely be hers to decide.

“Right now it is an empty plate,” Winter said. “I really think the most important thing is to give her time to breathe and get acclimated to being a private citizen again, knowing that she doesn’t have to tell people where she’s going to go, and we don’t have to put out an advisory if she’s going to go walk around a museum.”

After that, “we have space, [and] an idea of the size of the staff” Mrs. Obama will need, Winter said. “Because she’s not the president, we don’t feel the same sense of urgency” to be up and running as soon as the administration ends.

Laura Bush described her first few weeks at home after her husband’s presidency ended as a relief. “I would get in bed at night and think, ‘Oh, now what do I have to do tomorrow?’ And then I would take this deep breath and think — ‘I don’t have to do anything tomorrow,’ ” she told The Washington Post in 2014.

Obama also needs time to “feel what it feels like to feel bored,” Winter said — although she adds there is a “hunger” for her voice in public life.

“When she’s ready, our group will come together, and we’ll do strategy. And we’ll talk about what does the first event for the new Michelle Obama look like. How do we want it to feel, and how does she want it to feel?” Winter said.

Their overarching strategy for Obama’s next phase is “sometimes less is more.” “She has such a powerful voice. You don’t have to augment with a lot of things,” Winter said.

The family will also need income, to support themselves as well as the post-White House staffs they are building. Obama, who was once her family’s primary breadwinner, hasn’t earned a salary in eight years. To earn money, former first ladies and presidents have accepted paid offers to speak — not always without controversy — in addition to championing favorite causes.

In the meantime, the president has said his wife is working on her memoir — another typical income-generating project for former first families — which is expected to net a multimillion-dollar advance.

“Probably down the line [there are] many books in her,” Winter said. “I think she’d be a wonderful children’s book author. We haven’t set up a process for that, [but] down the line it would be a natural way to exhale from an experience like this.”

In final speech, emotional Michelle Obama tells young people ‘don’t be afraid'

During her final official speech as first lady, an emotional Michelle Obama urged young people to be empowered and lead 'with hope, never fear.' (Reuters)

Now that she has held her last official events, Michelle Obama and Winter’s most pressing concern is moving from the White House to the 8,200-square-foot home the Obamas will be renting in Washington’s Kalorama neighborhood. The family will stay in the city for at least two years while their daughter Sasha finishes high school.

Winter served as the point person in the White House guarding the Obamas’ time together as a family and overseeing the compilation of the first lady’s briefing books — a job focused more on logistics than policy.

Winter has practically lived with Obama since February 2007, first in Chicago and later on call to the White House, said Tina Tchen, the first lady’s White House chief of staff. (Tchen will not stay with Obama in the post-presidency; she plans to return to Chicago, where she was a corporate lawyer and early political booster of Barack Obama.)

Winter “knows what [Michelle Obama] needs on the weekends. She knows what the girls need, and she has a relationship not just with Mrs. Obama, but with the entire family,” said Tchen. “And now, after this long period of time, [she] can anticipate what kinds of things will they need to know about.”

She also has an uncanny memory for Michelle Obama’s events — and attire.

“I have felt like I have always worked for a family before a first lady,” Winter said. “I have made it my priority when we are in meetings and doing long-range planning [to remember] things like ballet performances, sporting events, parent-teacher conferences. All that stuff comes first.” She also knows Obama’s disparate groups of friends and has helped her move easily around Washington for her exercise classes, concerts, restaurant dates and walks in Rock Creek Park, a circuit she is likely to continue as she stays in the city as a private citizen.

“Washington to politicians is like L.A. to actors. At some point, they become less interesting,” Winter said of Obama’s experience. “She goes all over town to different SoulCycle classes and people see her, and it’s almost passé. People don’t necessarily whip out their cellphones anymore, and they definitely don’t approach her.”

Obama told Winfrey recently that she has given up hope of anonymity but aims to find a new normal.

“I’ve found that if you just flow into a pattern of life with people, they give you space to come in. That’s happened at my kids’ school and the places where I go and work out,” she said. “I hope to find a way to seamlessly work my way into a normal life. It’s going to take time, but I’m going to slowly.”

Krissah Thompson began writing for The Washington Post in 2001. She has been a business reporter, covered presidential campaigns and written about civil rights and race. More recently, she has covered the first lady's office, politics and culture.  Follow @Krissah30