My Job in One Outfit: The Microsoft Program Leader Who Writes Books and Designed Her Own Jacket

Can you say "polymath" again?

Street fashion, Bag, Urban design, Tower block, Commercial building, Condominium,
(Image credit: Tyler Joe)

When I was explaining the concept of this new series—professional women and heroic displays of badass-ery all condensed into a single exemplary ensemble—Dona Sarkar, leader of the Windows Insider Program, stopped me. For her, at least, it should be "My Life in One Outfit," because she hasn't got just one job.

Building holograms. Identifying applications for those holograms (like remote surgery or city planning or children's stories). Leading a team of developers. Starting her own fashion line. Writing novels. Here, see the outfit that defines her incredible, kaleidoscopic life—even though, yes, summing everything up would be impossible to do. 

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(Image credit: Tyler Joe, design by Dana Tepper)

1. "The Surface Book has changed the way I create, because I'm an analog creature. Whenever I'm planning something, whether it's a product, a novel, or a fashion project, I have to go get paper and a pen, and draw or write it. My old process was drawing something, taking a picture of it, and losing it. So the Surface Book completely changed everything because the rubberized tip of the pen makes it feel like I'm writing on paper even though I'm writing on a screen. And I just click the top of the pen, it opens a OneNote. I draw or I
write, and it saves it in the cloud immediately. So I've never lost anything since. I've written an entire novel on it on a plane."

"I found that, rather than changing to fit other people's expectations, I'm just going to be myself and show that a software engineer can look like me."

2.  "These boots I call 'the negotiation boots.' They're Jeffrey Campbell Litas, and I've had them for six years. I got them as a gift to myself after I got a promotion. I call them my negotiation boots because whenever I'm about to go in for a negotiation, whether that's for myself or for my team or on behalf of a product or customer, I put those on and I stand taller, I'm fiercer, and I've never lost one." 

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(Image credit: Tyler Joe)

3. "Ted Baker makes these midi sheath dresses that I love because they work so well for evening, but with a jacket over it, it works incredibly well for day. It's long and really great neoprene fabric, no wrinkles—I travel a ton. So I just throw this in my suitcase and can pull it out, and it always looks good, no matter what. And I love that it's a color and a print. In a place where I have to meet someone, I can tell them I'm in the printed dress rather than 'I'm in the black jacket or blue backpack,' or something generic." 

4. "I designed it in 3-D and spent a lot of time tweaking the shoulders and the waist and walking around it, just rotating this object over and over. Then I made the prototype sample. I'm working with a factory in Hong Kong to actually make the production. It's got a very strong shoulder because people carry a lot of weight on their shoulders. So the shoulders are there to remind people that their shoulders are broader and stronger than they even imagine. I want the person who wears that jacket to be noticed the second they walk into the room, and I want it to make them stand up taller. And when people see them, they realize, that person means business, that this is not a person I should mess with."

"'The height of my heels has nothing to do with my technical abilities. They're not related.'"

"At the very beginning, of my career, I would show up in over-the-knee boots, 5-inch heels, and people would just stare at me and ask, 'Oh, you must be in marketing.' And I said, 'No, I'm a software engineer.' And they'd say 'But you don't look like a software engineer.' I found that, rather than changing to fit other people's expectations, I'm just going to be myself and show that a software engineer can look like me—because if I changed who I was then, that stereotype lives on, that someone who wears over-the-knee boots cannot be a software engineer. And the reason that the stereotype has lived on so long is that people have changed to fit the mold.I've gotten a number of emails and texts and messages saying 'I've never seen someone present such hardcore technical content wearing over-the-knee Stuart Weitzmans.' And I said, 'The height of my heels has nothing to do with my technical abilities. They're not related.'"

5."Last weekend, I organized a hackathon and invited 100 developers, art, sound people to come together and think about the various industries they're involved in. We had a lot of people from medical, we had a lot of people from architecture, we had a lot of people from art. So they came together, they formed teams, they came up with an idea. My team and I taught them to build a holographic app to solve a specific problem. Always be hustling."

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(Image credit: Tyler Joe)

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Chelsea Peng
Assistant Editor

Chelsea Peng is a writer and editor who was formerly the assistant editor at She's also worked for The Strategist and Refinery29, and is a graduate of Northwestern University. On her tombstone, she would like a GIF of herself that's better than the one that already exists on the Internet and a free fro-yo machine. Besides frozen dairy products, she's into pirates, carbs, Balzac, and snacking so hard she has to go lie down.