Willow leads the Customer Operations team at Scale. She is a former director of logistics at Amazon.com, a graduate of MIT’s Leaders for Global Operations program, and a former captain in the U.S. Army’s Military Police Corps.

I am a transgender pioneer within the military and corporate world, with a career spanning 12 years in the U.S. Army, MIT, Amazon, and Scale. Here are some of the things I learned along the way.

Why I decided to change my gender

I had decided to change my gender while in a concrete shelter from rocket attacks right before returning from deployment in Afghanistan. Rockets in this context were not particularly threatening, but sitting in a concrete shelter at night waiting for the sirens to go off can naturally lead to introspection.

I had no intention of being a pioneer. It was a simple search for my own personal happiness. I felt like any other choice would be the wrong one. It was too much of a big and scary decision to think at all about how my career would shape out.

There were deliberate risks I took and risks that I didn’t expect and needed help with.

Back in the states, I was the first officer in my military unit to be out as bisexual after the repeal of “Don’t Ask, Don’t Tell” (DADT). This was a deliberate risk: my personal and professional lives didn’t intersect, but I thought that someone should be out as an example if other soldiers wanted to come out.

I still felt like I had a vulnerable secret, as being transgender was still prohibited, and my plans to transition after departure were carefully guarded even as I changed my legal name and started living as female while on leave. My commanding officer was overtly hostile towards the repeal of DADT. After one staff call in which he used “faggoty” as a term of derision, I grew concerned about whether or not I would be able to leave the Army on my own terms. I need not have been concerned, however. Senior members of the staff met with the commander over his comments, and he decided to leave the Army over the pace of change. Like me, but for different reasons, he was voting with his feet.

Returning to graduate school, I was the first openly transgender person in my program. I was one of two transgender students to tell my story to the school’s leaders in an ultimately successful bid to change insurance coverage policies for all students. Not all was respect and smooth sailing; in one emotionally crushing case, two teachers complained to my program admin about me using the restrooms that matched my gender identity (it seems strange to type this - much has changed in eight years). My friends calmed me down, and school administrators used the complaint as a teaching moment for the faculty.

The only [other] in the room?

As my civilian career advanced at Amazon and at Scale, I became more aware of how being transgender would shape my approach to work. No matter the realities of my professional role, I always feel like a bit of an outsider. It has been argued by folks more articulate and demonstrated in studies that diverse perspectives lead to better decisions, and clearer identification of risks. This is a good thing.

The downside to feeling like an outsider is always feeling the need to push myself harder, to prove myself better, and to hold myself to an extremely high internal standard - and to always fear slipping. This approach to work has helped me advance quickly, and made me bold, but it is exhausting at times and ultimately rooted in fear.

One of the factors in my recent decision to join Scale was that many company leaders identify with the LGBTQ community. I want to help build the future without worrying so much about how I fit in it. Taking a role at a smaller, fast-moving startup with less formal structure has been awesome. There’s a sense of purpose and mission and a rapid flow of ideas that I feel I can really be part of.

Transgender people have always existed in one way or another, before society’s own peculiarities and social constructs started calling it a “new thing.” I wrote earlier that I was the first openly transgender applicant at my grad school program. It is highly likely that there were transgender people there before, and it is likely that some of my classmates were transgender and simply hadn’t decided to transition yet. It is important to remember that an individual story cannot represent a community, especially with big variation in opportunity and privilege shaping peoples’ lives.

Advice for folks feeling like outsiders

There are a few things that I wish I’d known earlier in my career. One piece of advice I got from a friend has stuck with me: “You will always think about yourself a lot more than others think about you.” That feeling of awkwardness, that one thing you did - most people simply won’t notice or remember. Our memories are inherently selective. Learn from your mistakes but choose to remember the good parts.

The other thing I wish I’d understood better earlier is to not be afraid to pick a mission with purpose. Early on, I picked assignments that seemed like the best value for the company’s ability to save money or expand programs and to advance my career. I left jobs and teams that I enjoyed to seek out the external trappings of success. Many people do this, but the feeling of validation seemed so necessary when I was uncertain of my place in society. Finding a team and a voice that makes me feel at home and a mission that serves a purpose I believe in has ultimately been more gratifying. Now, what the people around me think matters more than what the world thinks.

Scale believes there is tremendous potential for AI technology to drive a revolution in true efficiency and productivity, across industries - this is a change for which I want a front row seat. I am glad I am able to take that seat feeling like I am no longer an outsider.