Years in industry?
21. I’ve been building applications for the web since 1994. I was lucky to have had the opportunity to get in when the web was new and relatively unformed, and to be a witness to (and participant in) its early stages of growth.

Who or what inspired your career in tech? 
My father was a huge inspiration to me. He was an electrical engineer, and he continues to be fascinated with all things technological. He bought us our first home computer, a TRS-80,  when I was a little kid. That’s the machine that let me learn how to program. Later we upgraded to a Commodore 64 and we worked on making a lot of really interesting projects, including a light pen, a robotic hand, and a morse code encoder/decoder that we interfaced with his ham radio. I got really bored with the games that were available in the early days, so I ended up writing my own. I was pretty sure from a young age that that’s what I would want to do with my life. Luckily I had a computer teacher in high school who recognized my potential. He created an individual curriculum just for me and also had me help him teach the class.

When I got to college I signed on as a Computer Science major. But the first class I took had us writing software for an ATM in C. I was bored out of my mind and it killed my interest in programming as a profession. I switched to English briefly and ended up dropping out of school. But I kept hacking on things in my free time, so I was ready when the world discovered the web, and I suddenly had marketable skills.

What’s been your best hack ever?
I do a lot of pairing, mentoring, and teaching. I used to be pretty aggressive about promoting “The Right Way” to solve a particular problem. When I paired, I would be the one to bring the overall implementation to the table. After a while I realized how patently unfair that approach was; it neither allowed for my partner to contribute to the design nor for me to learn. So I adopted a new technique, based on the idea of the Socratic method of asking questions rather than making statements. This approach allows plenty of space for other people to express their ideas in a constructive way, and it keeps me from rushing to make decisions— often wrong decisions— too quickly. I found that the difference that this makes is huge and frankly pretty humbling. I try to adopt it now in other spheres of life, away from the keyboard, as well.

What has been your greatest career challenge and how have you handled it?
I lost my job the same month that I began my gender transition. So at the lowest point of my life in terms of my self-esteem and confidence, I had to put myself out there and try to find a new job. It was a terrifying experience, but I had no choice. I had to come to terms with the fact that I was in a stressful, uncertain period of my life but that my skills and talents were still valuable. I had to convince myself of this so that I could convince potential employers of the same thing. I know that I was awkward and shy and terrified throughout the whole process, but I was determined to make it work.

I should point out that I received tremendous support from my friends and peers within the tech community and beyond. I don’t think I could have made it without them. The tech feminist community was especially welcoming to me and kept me from bottoming out.

What is your biggest career success to date?
About ten years ago I started getting promoted, from developer to senior developer to lead to architect. Eventually I was made a director, and then Chief Solutions Architect at a small startup. But the higher up I got on the management chain, the less code I wrote. Eventually I figured out that, although I love being a leader, I’m happiest when I am writing code. So I gave up titles and promotions and started over as a regular old developer. I have learned that I can still bring leadership skills to bear and help others be successful without having a formal title that goes with that responsibility. Returning to the code and more personal levels of interaction made me feel satisfied and content. I count that as a success.

Who are your role models?
I have two, one fictional and one real. Alice, from the Lewis Carroll books, has always been my hero. She stepped out of the world she knew into completely unchartered territory, where all the rules were different and everything seemed upside-down and backwards. Yet she persevered, stayed true to herself, and found her way through. I try to live my life that way, too.

My other biggest inspiration is Nikola Tesla. He was an absolutely brilliant scientist who was not afraid to test the limits of what was possible, of what was known. He followed his intuition and never turned away from a challenge. He worked under tremendous constraints, from the tools available to him to a chronic lack of funding, and proceeded to transform the world around us. On the negative side, he had a hard time seeing things through once the spark of the idea was realized. In that way, his rival Thomas Edison surpassed him. Edison focused on repeatability, practical matters like money, and predictable, evolutionary advances. Tesla was the revolutionary thinker. I believe that as technologists we oscillate between Tesla and Edison modes of operation, sometimes following our crazy dreams and sometimes putting our heads down and doing what needs to be done. I think that without Tesla, Edison would have been much less successful, and vice versa. So in my work I always look for that balance, I look for the Edison to my inner Tesla.

If you could go back in time, what’s one tip you’d give your teenage self?
Learn and practice empathy on every occasion. It took a long time for me to realize the importance of empathy in every sphere of life, personal and professional. I think that that lesson would have helped me mature more quickly, learn more from the people around me, and overall be a better person.

What do you do when you’re not kicking butt at work?
I volunteer about 6 hours a week, working to get (and keep) more women in tech. I co-organize Chicago Women Developers, and run our weekly open Hack Nights. I also do one-on-one mentoring for a couple of young women developers. Aside from that, I like to draw, make music, and play board games. I’m also really fond of cinema from the 1930s and 40s.

Flats, heels or kicks? 
Boots. Definitely boots.

Best career advice book? 
I tried reading quite a few of these kinds of books, especially when I started getting into management. I found most of them to be pretty bad. The two that stand out in my memory, though, are Guy Kawasaki’s Rules for Revolutionaries and The Goal by Eliyahu M. Goldratt. Although far from agreeing with many of the points made in either book, they definitely influenced the way that I thought about my career and the work that I was doing.

Who are the women in tech whom you most admire and why?
I have immense respect for the women who are not only holding down their day jobs in tech but who are also working to make the world a better place for underrepresented people in our field. The amount of energy, tenacity, and stamina that this kind of work takes is astounding, and I’m in awe of the people who are engaged in it. I find them very inspiring as individuals and as a community, and I’m thankful for the opportunity to work with them. They embraced and supported me from the very beginning of my gender transition, and I try very hard to pay that forward.

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