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Ex-Microsoft Exec Living The Boomer Fantasy: Meaningful Work

This article is more than 10 years old.

This story appears in the June 23, 2013 issue of Forbes. Subscribe

"I wanted to get my hands dirty," Stonesifer says later, her palms still purple-tinged, as she explains why in April she became president and CEO of Martha's Table.

At 57 Stonesifer could afford to do anything or nothing at all. In her 30s she was the highest-ranking woman at Microsoft, running its interactive media division and overseeing the development of MSNBC, the online magazine Slate and Encarta, one of the first digital encyclopedias. But when she turned 40 she no longer felt fully engaged in the business and "retired" to get more involved in her two kids' lives and, she says, "figure out what that next chapter for me was to be."

She didn't have long to think. In 1997 Bill and Melinda Gates recruited her to launch their library foundation. "My job at the beginning was connecting hundreds of libraries to the Internet. So it was very boots on the ground, sleeves rolled up. It was fabulous--one of the happiest times in my life," she recalls.

By 2000 she had become the first CEO of the Bill & Melinda Gates Foundation, the largest private charitable foundation in the world, with $36.4 billion in assets and 1,116 employees as of the end of 2012. Her role, she says, became that of the "benevolent bureaucrat": She built an organization, personally reviewed more than 100 of the 3,000 grant applications received each month and traveled the world, pursuing partners for the foundation's work promoting solutions to global health crises.

In 2008, with her kids grown and Gates about to relinquish the day-to-day running of Microsoft to focus on the foundation, Stonesifer figured it was time for yet another new act. She resigned as CEO and took on a variety of projects, including a three-year stint chairing the Smithsonian Institution's Board of Regents and the chairmanship of a White House council that President Obama created to look for solutions to the problems of out-of-school, out-of-work 16- to 24-year-olds. (She still chairs it.)

Stonesifer and her second husband, journalist Michael Kinsley, the founding editor of Slate, started dividing their time between Seattle and Washington, D.C., and last summer they decided to make the nation's capital their full-time home (in part because Stonesifer's daughter lives there, working for USAid). Then, last fall, she heard through a friend that Martha's Table was looking for a new CEO.

It represented, among other things, a chance to get back to her philanthropic roots. Stonesifer's Irish-Catholic parents had nine kids and a deep commitment to helping the poor in their Indianapolis community, working in food banks and soup kitchens and taking foster children into their already crowded home. "You began realizing you were to be responsible for the community, literally right inside the house," she recalls. "There was even one foster girl named Patty, who shared my room. The biggest lesson of a big family is that it's not about you." Even while running the Gates Foundation, Stonesifer volunteered at a Seattle soup kitchen when she could, bringing her two teenagers along, just as her parents had brought her along to work.

She certainly had other options. No doubt a national charity would have been thrilled to hire her. But after leaving Gates, Stonesifer says, she used the transition period "to ask, prestige aside, title aside, what did I want to do all day?" Her answer, delivered in her unaffected Midwestern style: "What I wanted to do is to get close and understand and stand with families and individuals who are trying to address poverty at the community level, at the personal family level."

Stonesifer's résumé is one of a kind, but she is also a poster child for a broader movement among those approaching what used to be considered retirement age. Instead of dreaming of sitting on the beach, baby boomers, in their fantasies (and sometimes in reality, too), are shifting into personally meaningful work for their second or third act.

She points to other bersuccessful corporate types--including New York Mayor Michael Bloomberg--who have gone on a career-shift path in one way or another, and reports running into lots of not-so-famous folks undertaking what she calls the "trusteeship" period of life. "We will see more and more philanthropic second-acters going forward," she predicts.

Sidebar: Tips For Moving Into The Non-Profit Sector

Stonesifer is adamant, however, that her new job is not an example of another boomer trend: downshifting. "I don't think I'm downshifting because that's when you are slowing down," she says. To the contrary, her latest move is part of a lifelong determination to stay fully engaged and to move on if she's not. "Keeping the neurons moving is what, to me, is full engagement," she adds. "Accepting this job is really about immersing myself in ideas and information and experiences that really take everything I've got."

A morning spent watching Stonesifer shows the meaning of full engagement. First up is a 7:30 a.m. breakfast meeting with a potential donor at Le Pain Quotidien (a moderately priced Belgian chain). Martha's Table receives about $4 million in cash and $2 million worth of food and clothing donations a year. But Stonesifer insists she won't be using her platinum-plated national contacts for fundraising.

"Our gifts are running a little ahead of last year, but it is not because I am going through my Rolodex," she says. As a grassroots local charity, she explains, Martha's Table must be built on "year after year after year of support by community members" who see it as "an important part of their trusteeship of being a citizen."

Before 9:00 she arrives at the charity's blocklong headquarters on 14th St. NW, just outside downtown D.C., and starts making the rounds, comfy in her $80 Tom's cotton-and-hemp ballet flats. (Besides being practical, the rubber-heeled shoes make a statement: Tom's pledges to give a pair of new shoes to a poor child for every pair you buy.)

She visits with the babies, toddlers and preschoolers at the day care center within the facility. The educational component was a big part of the charity's draw for Stonesifer, who considers it key to breaking the cycle of poverty.

Currently, there are 93 kids, almost all minority, in the program, which serves children from 3 months to 4 years. But in a city with 110,000 residents--30% of them children--living in poverty, the need is greater, and this fall Martha's Table will use a government grant to boost enrollment to 119.

The charity also runs an afterschool program for 250 older kids. In the summer they spend all day in a program with education, meals and a full plate of enrichment activities, ranging from trips to the National Archives and Mount Vernon to computer classes to tending a greenhouse garden. (Preteens are offered a program where they work with legal mentors and learn to debate issues.)

Then Stonesifer heads down the hall to visit with what is, on that day, an all-female team of volunteer retirees chopping their way through 50-pound bags of carrots, onions and potatoes to make shepherd's pie for the night's meal. Martha's Table makes prodigious use of volunteers--more than 10,000 annually, including schoolkids and the homeless as well as the Obamas and corporate CEOs. Yes, 10,000 sounds like a lot, but Martha's Table has spent years building ties to local churches and schools. (See box.)

She zips across the Anacostia River to the opening of Martha's Outfitters, a thrift store in Washington's poorest quadrant. The store, the second of its kind the charity has opened, provides free clothing and housewares to low-income families referred by partner agencies such as Catholic Charities. It also sells donated items to raise funds.

With the discipline of a former Microsoft exec, Stonesifer budgets her time carefully: She aims to spend a third of it working on broad issues related to child hunger in D.C. and nationally; a third on a strategic plan for the future of Martha's Table; and a third interacting with staffers, volunteers and clients.

Given her Microsoft wealth, she takes no salary from Martha's Table, just as she took none from the Gates Foundation. She's also a longtime board member of Amazon.com, where directors are paid in stock grants; her current holdings in the e-commerce giant are worth more than $10 million.

"I was lucky that I had a lot of success really young," says Stonesifer. With a nod to the burdens of others, she notes that not having to worry about paying for her kids' college or her parents' care freed her to think about what matters to her. The place she has come to is summed up by a motto imprinted on her personal notepaper: "If you want to go fast, go alone. If you want to go far, go together."

Sidebar: Common Ground

How does a relatively small nonprofit like Martha's Table bring in 10,000 volunteers a year?

Call it commitment. Or smart marketing.

Since its founding in 1980 by a sociology professor and a Jesuit priest, Martha's Table has engaged in relentless outreach: to the poor and homeless on one end, and to schools, churches, synagogues, workplaces, seniors groups and other sources of volunteers at the other.

Martha's Table is now an institution, a Washington destination for visiting dignitaries and locals alike.

Over the years volunteers have included President Obama and family; BET Chairman and CEO Debra Lee; Microsoft founder Bill Gates; and the wives of Mexican president Vicente Fox, President George W. Bush and Russian premier Boris Yeltsin. PricewaterhouseCoopers, the Royal Bank of Canada and Exxon Mobil all regularly send workers. On Thanksgiving whole families descend on the place.

The result: Besides feeding the poor, Martha's Table now feeds a fragile sense of community in what is by and large a transient and divided city.

For more tips for moving into a job with meaning:

Follow me on Twitter, @KerryHannon I'm the author of Great Jobs for Everyone 50+: Finding Work That Keeps You Happy and Healthy … And Pays the Bills (John Wiley & Sons), available here www.kerryhannon.com. Check out my column at AARP. My weekly column  at PBS's NextAvenue.org is here.