Digital Diplomacy
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Digital Diplomacy

Leaving Microsoft to work in Government.

A millennial’s odyssey to serve in civic technology.

Here’s a photo of me at work in December of 2018… and this is me now.

It’s 2019, I left my cushy millennial tech job at Microsoft, moved across the country, and took a role in US Government as a White House Presidential Innovation Fellow. Some people think I’m crazy, others think I’m brave. But everyone seems to have the same question — What made you decide to take this leap? Why now? Why leave a “good deal”? And why Government?

Here’s my best attempt at explaining what led me on this crazy voyage. The truth is, there was no single moment, no bite-sized answer. I didn’t wake up and suddenly have the conviction to flip my world. My journey to government is the culmination of a chain of events that eventually reached a tipping point. This is my story.

Part 1 — Genesis

Where it all began.

Before I explain how I got to this destination, I think it’s important to start with where I began. While I was born in a small town in Wisconsin, I grew up in Hong Kong — one of the most densely populated metropolitan cities in the world. I was constantly surrounded by two things, people and structures. The city orchestrates a seamless harmony of 7 million people every day. Small optimizations, and well designed micro-experiences, made tremendous impact at scale. The train running 2 minutes behind for 7 million commuters meant losing 9722 collective days of work. I was enamored with this concept of scale and efficiency from a young age, and I grew an appreciation for how everyday design could influence our lives.

This has largely been the river that’s run through my life. My favorite subjects in school? Design & Technology, Art, and Human Geography (I took them all at higher-level for IB some decade ago). Building experiences for people, and telling stories to audiences, became my thing. Drawn to endeavors centered around mission, design, and scale, I worked at Disney, NASA, and Adobe before joining Microsoft. I’ve spent the last 5 years designing experiences for hundreds of millions of global users.

Journey at Microsoft

I came to Microsoft to fulfill a dream: to design user experiences that made people’s lives better every day. The first team I worked on when I joined the company was Microsoft Edge. It was an opportunity to reinvent the single most used application on Windows, the browser. The promise and opportunity was (and still is) immense — to be a part of a team that shapes how we experience modern life. The browser has become nothing short of our window to the world. I was bright eyed and bushy tailed.

Microsoft taught me everything I know today about building product. It taught me how to call a server from a client, how to manage a never-ending inbox, and how to build with user-empathy in mind — I learned about inclusive design and the importance of accessibility (things they don’t teach you in art school). I shared the same vision they had for the world — needless to say, I drank the corporate Kool-aid.

But like clock-work, every early-in-career employee has an existential crisis about two years in. The difference for me? Mine coincided with the last election. While not personal, it felt personal. I asked myself how we got here… How I lost sight of things. And why I was spending my days helping a giant corporation monetize attention spans, or sell homepage shopping scenarios. That week, my 1–1 with my manager was extra philosophical. I think I even told him I was ready to leave, and when he asked me where I wanted to go… I responded “I have no idea… maybe the Peace Corps.” He said, “before you make any rash decisions — I want you to think about what you came here to do, and what would be something you would want to work on if you stayed.” I took to the drawing board and reminded myself of how I got here.

Finding my corner of the Company

Over the next few nights, I put together a new pitch “Browse and Give” — it was a product-engineering approach to driving impact and engagement through our products (and not just through our philanthropy). I was convinced Microsoft wasn’t going to win a 20 year browser war over speed or security (regardless of exceeding competitor performance benchmarks). But I fervently believed we could position ourselves as a product leader with a mission — a force for good. After all, Microsoft has a longstanding history in giving back. Ignited by a fire fueled by our social-political climate, I was on a new mission. I came to the realization that our world’s reality is a by-product of everyone’s collective action (or inaction). It was in that moment when I made a pledge with myself — that I would never spend my human ingenuity on things I didn’t passionately believe in. Confronted with myself, I was determined to find a way to reconcile my day-job with my soul.

Moving like a hurricane, I socialized my new pitch across the company. I started with soliciting feedback from mentors far and wide, refining and hardening my ideas along the way. Once my napkin drawing graduated into a full fledged product deck, I set up meetings with as many senior leaders I could reach… from Azure to Bing to Xbox. Eventually, I had an opportunity to present it to my Corporate Vice President, and soon after, got the green light to drive this strategy full time. I began reporting to his Chief of Staff, and managed to carve out my own role at Microsoft. Looking back, this was a unicorn millennial dream job. Having sponsorship, resource backing, autonomy, and end-to-end ownership of a new project. This incredible opportunity kept me at the company for another two years, in which time — my personal voyage for purpose completely transcended to new heights.

Part 2 — Transformation

This is where the plot thickens.

Convincing someone to bet on me is the easy part. Actually figuring out the job is the hard part. Truthfully, I had impostor syndrome. I was given an opportunity to own and shape an ambiguous body of work. Outside of being a value-driven person and wanting to “do good”… I didn’t actually have experience in building social-impact product. But I’ve never been one to shy away from a challenge, and the antidote to impostor syndrome is expertise. So I dove head first into anything and everything social impact.

I spent the first 6 months applying our innovation process to dissecting and understanding the impact space. I quickly became a preeminent expert in my org on social-impact initiatives — researching over 200 case studies of companies and projects from the fad of Toms, to failed Pepsi ads.

Like “method acting,” “method research” is a user-centered approach my organization took to the next level of customer obsession. The premise? In order to deeply understand building for a given user, you must live, empathize, and experience their reality to immerse yourself in understanding its complexity — as fully as humanly possible. So I did just that.

I put myself in the shoes of the stakeholders, users, and experts I was about to design for. Little did I know, taking the journey itself was about to change everything.

Nepal — The Trip that Started it All

Two plane connections and an 8 hour bus ride later, I arrived in a remote village in the countryside of the Himalayas. The school was merely a physical structure. There were few desks, a handful of dated textbooks, and it was completely void of technology (and electricity). I visited with the intention of understanding how technology might be able to help a partnering nonprofit achieve their mission of poverty reduction, or be a gateway to unlocking access to literacy and learning. I was dumbfounded when the Principal said I wasn’t the first person from Microsoft to visit this beyond-remote school. I saw a placard on the wall from an organization called Room to Read.

I looked up the organization’s story. As it turns out, the nonprofit was started by a former Microsoft executive, John Wood. After a backpacking trip through Nepal in the late 90's, John left Microsoft at the height of the (former) glory days of Windows 95 to pursue bringing literacy to children everywhere. He even wrote a book about it…

Book: “Leaving Microsoft to Change the World: An Entrepreneur’s Odyssey to Educate the World’s Children”

The title of this post is very much an homage to John. Title alone, his story planted seeds in my mind and ignited a spark in me to begin my own search for a higher calling. If I was wrestling with a corporate existential crisis before, this book made things much worse. I continued to ask myself “what is something worthy enough for me to drop everything to pursue?”

Days for Girls — The cause that inspired me to “Lean In”… for others.

I began making a list of causes I cared deeply about… climate change, plastic in the sea, education, and advancing women’s rights. The last one was easily the most personal. As a woman in tech, this conversation is inescapable. Unlike the other causes, this was a battle I was already in the trenches fighting.

In a conversation with a non-profit leader, I shared my passion for empowering women and girls to thrive. The leader lit up and remarked — “I would love to introduce you to Days for Girls.” That’s when I met Celeste Mergens, one of my heroes, and the founder of Days for Girls International. After watching her riveting TED Talk and story, I couldn’t help but get involved with the organization. Days for Girls is a nonprofit focused on bringing women and girls access to sustainable feminine hygiene solutions, as well as economic opportunity. Here’s my 3 minute bit on it…

How do we not have a universal way of managing something so fundamental? At first, I didn’t know how to reconcile the emotions I was flooded with. I worked at a workplace where pads and tampons are free. And the monthly discomfort, if any, was a question of whether or not I remembered to bring my own preferred brand, or instead need to sucker up and use the generic.

Not a day goes by at Microsoft where we’re not reminded of our corporate mission…“To empower every individual and every organization to do more.” The opportunity behind this mission completely changed for me after learning about “period poverty.” Forget syncing email, designing spreadsheets, and breaking glass ceilings… “empowerment” for hundreds of millions of women around the world today is as simple as being able to be productive every day of the month. In this moment, I realized that the most important problems our society faces, aren’t the most technical. By virtue of my interest in scale and impact — I may have just found a cause worthy of all my attention.

Effective Altruism — Pausing to get tactical.

But amidst all this social impact research, I interrogated business models, frameworks, theory of change, and operationalizing social enterprises. After all — make no mistake, I understood that my day-job (and bonus) still depended on figuring out how to turn a buck for Microsoft.

In synthesizing my research, one concept surfaced time and time again: effective altruism. It’s basically a talent-resource supply-demand optimization.

Effective Altruism = Greatest Superpower + Greatest Need

As an example, lawyers volunteering to pack lunch bags might not be more valuable to a cause than simply donating one billable hour, and allowing them to allocate spending. Thus, the most effective way you might be able to provide meaningful altruism may not feel the most rewarding. It’s about driving lean impact.

I thought about what I could uniquely offer this organization, and where my talents were needed. Instead of sewing kits or making posters, I joined their Board of Directors — offering my talent and passion for organizational leadership, strategy, evangelism, and strategic partnerships. This work continues to be incredibly humbling and rewarding. And I’m so grateful to get to support and strengthen their mission in a way that they need. So my search for purpose in my day-job continues.

Leadership Tomorrow — the catalyst to step up in civics

Few training's have changed my life in the way Leadership Tomorrow has. Leadership Tomorrow is a 9-month civic leadership program that brings 80 leaders across the private, public, and nonprofit sector together. The premise is to cultivate leadership in the Pacific Northwest to tackle issues facing our region. I went in expecting a training on unconscious bias, and gaining new awareness for personal blind spots. If I was lucky, I might even walk out with a few new tactics to navigate those. I got what I expected, and so much more.

I felt like I not only went on a personal leadership journey, but also a woke racial-equity journey, AND a power and privilege intervention all together. Without being overly dramatic — it was a transcendent experience for me during this searching phase in my life. The course focused heavily on race as a leadership issue. We dissected, interrogated, and tried to unpack the layers to this onion. It was deep. It was personal. It was emotional. Race in our country has historically been a black and white conversation. But I began unpacking the topic of race synchronously as Asian pop-culture was on the rise — Ali Wong, Crazy Rich Asians, Subtle Asian Traits. Timing put this all in the forefront of confronting culture, and I began challenging what this all meant for me as an Asian-American woman.

Leadership Tomorrow shifted paradigms within myself. I realized I wasn’t on a journey of becoming, I was on a journey of defining. The question I had to ask myself wasn’t if I was going to become a leader, but rather what kind of leader I want to be. For the first time, I consciously stepped-in to understanding (and exercising) my power and privilege.

The one-two punch of Leadership Tomorrow? Each month, we learned about a different social issue: homelessness, education, affordable housing, the opioid epidemic, redlining, and many more. This was when I truly grew a heightened interest in Government. For the first time, I was exposed to working alongside cross-sector leaders trying to solve complex social issues. And I realized just how critical of a role local, state and federal Government play in the overall health and well-being of our communities. So when I learned about the Presidential Innovation Fellows, the US Digital Service, and 18F, I felt like I found the thing I was looking for all this time. For once, I saw a meaningful way for me to participate in Government. I applied for the job, and several interviews and fingerprints later — I had an offer.

Part 3 — Pulling the trigger.

So I got a job offer in government... But what gave me the confidence and conviction to actually do it?

The Commencement Speech I Never Forgot

Anytime I’m about to make a career change or job switch in my life, I come back to one habit — watching commencement speeches for wisdom and inspiration. There’s one speech that throughout the years I always come back to, and that’s Admiral McRaven’s 2014 commencement address.

Watching this video, I thought to myself… Could I look back at my career and be able to say “[Doing this thing] has been the greatest honor of my life.” Honestly, I wasn’t completely convinced.

This speech was also so patriotic, it reminded me of one of the greatest speeches of all time, JFK — “ask not what your country can do for you, ask what you can do for your country. I thought deeply about this, placing it in my own reality. My life was largely oriented around my workplace. At the point where your company takes care of your transportation, health care, education programs, fitness incentives, retirement planning, and beyond, it effectively plays the role of providing social services for its employees. Mimicking and replacing the role of government on the individual level, big tech has become a haven for “corporate socialism.” So I pondered a notion…“ask not what your corporation can do for you, ask what you can do for your corporation” — I couldn’t even finish the thought before acknowledging to myself how ridiculous and laughable the thought of this was. There’s no such thing as corporate loyalty. And that’s because companies don’t really take care of people — they take care of financial interests. Which is why millennials change jobs faster than they change yoga instructors.

In that moment, I realized that regardless of sector, industry, or structure, I simply want to spend my time doing something honorable and worthwhile. Something mission driven where I was in the trenches with passionate, talented, capable people trying to be a part of something bigger than themselves. I want to leave a legacy that isn’t just my own. That would be epic. That would be the greatest honor of my life.

Amidst everything from election integrity, to the failed launch of, to gross wealth inequity on the rise — there’s never been a more pressing time to participate in Government.

Why the US Department of Veterans Affairs?

I interviewed with a few different Government agencies but decided to join the US Department of Veterans Affairs (VA). Here’s my math on this…

Greatest Need — Our government services are failing to keep up with the demands of the 21st century. Veterans are some of our most vulnerable citizens across America today. They serve and protect our country with their lives — they deserve our service back.

Greatest Superpower — I’m not a very technical PM, in fact, I’m not a technical PM at all. But I’m a hustle-PM. I identify opportunity, translate concepts, and sell strategic visions. I herd cats, and manage hairy cross-team dependencies. Working under a Chief of Staff, I inadvertently got to watch what it took to run a giant organization — how to build consensus, unblock roadblocks, identify instrumental people, and find alternative paths to getting things done. Above all else, I straddle design and PM, being a steward for human-centered design and inclusive design in building large-scale consumer experiences.

Effective Altruism — There’s no tougher customer design challenge than building digital services for Veterans. Age, access, accessibility, connectivity — if you can build successful product here, you can build successful product anywhere. With over 370,000 employees, the VA is also notorious for endless bureaucracy. Having a heightened tolerance for people-politics and stamina for herding cats is not just needed, it’s necessary. As a Presidential Innovation Fellow, I get to bring my core functional strengths to an agency that needs it the most. In hindsight, Microsoft was basic training for Government.

The Green Elephant in the Room

What about my “career” future? My velocity? My bonus… perks… pay cut? Why leave a great deal for a headache? There’s been no shortage of people asking me this, so let me address the green elephant in the room. Especially since, as a woman in tech, it seems counter-intuitive to leave money on the table.

My answer? Gratitude, paying it forward, and having the courage to step into my power and privilege. For peers that share a similar educational background and path to big tech, we are often living a multi-generational American dream. Our parents tirelessly worked middle-class jobs to provide a brighter future for us. We went off to college, picked a major out of moderate interest, and if we were serendipitous enough to find our path to tech, we graduate into a jackpot job. With just 1 day of work experience in big tech, we’re making more money than many of our parents are at the height of their careers. $XXX,XXX for just showing up.

It doesn’t take long scrolling through Blind, to find that this sentiment is pervasive. But privilege is no one’s fault. And for those who have been handed it — it’s my belief that we should have the courage to be responsible in how we exercise it. We get to live gloriously today as a factor of what the previous generation has built and given to us. Every single day, I’m grateful for how hard my parents and grandparents have worked so that I could live comfortably and thrive. The real question is — what future are we giving to the next generation? What world do you want your children and grandchildren to live in? What world do you want to grow old in? The answer should be one better than today’s. It takes courage and sacrifice to protect this promise. To all my peers rising alongside each other, we hold more power than we realize. And the burden will be on us to solve today’s greatest challenges.

Hope is not a strategy.

So for me, honoring those who came before me, and service to those coming after me, matter more than “just taking mine.”

Inspiration is the greatest placebo.

Finally, one of my dearest mentors at Microsoft, Dona Sarkar, continues to be my hero whether she fully realizes it or not. She’s a total boss lady. Anytime I’ve been at a fork in my career or just needed a pep talk on impostor syndrome, she’s always given me the time of day to talk through this together. Beyond that, she leads by example. She inspires me because she fearlessly pursues things she’s either passionate about or believes in. She’s not afraid to take on the unknown. She talks about everyone having that “thing” that they want to do, but there’s an invisible wall and they’re afraid to do it. She coins it #DoTheThing — just do the thing you’ve been dreaming of. But actually. Simply start. Like, today. Because… the world needs it. Seeing her do the thing, inspires me to do my thing. My thing is different. It’s not writing fiction or becoming a fashion designer — it’s telling stories, connecting with humans, and building experiences that move people. While Dona didn’t necessarily materially do anything to lead me to take a job in government — inspiration is the greatest placebo. If she can #DoTheThing, I can #DoTheThing. And you, yes you, can #DoTheThing. Surround yourself with good vibes — it pays dividends to the soul.

Present day.

So… One woke journey to Nepal. Effective Altruism. JFK. #DoTheThing. And a culmination of our circumstances has given me no choice but to pack up my Prius, drive cross-country, and embark on my great American journey. It was either the perfect storm, or the universe repeatedly smacking me in the face with a higher calling. Courage isn’t built in a day. And truthfully, you’ll never be ready for the scariest leaps of faith. But you shouldn’t do things just because they are easy, or trivially hard for that matter. You should do them because they matter. And fixing our systems, our communities, our country, and our government has never been more important.

Going from Microsoft to Government, people seem to think I’m going to be traveling back in time. But in reality, I’m here to help build the future.

Join me in engineering a brighter tomorrow, because — it’s ours.




Tech, digital, and innovation, at the intersection with policy, government, and social good.

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Clarice Chan

Clarice Chan

Creative. Technologist. Conversation enthusiast.

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