So I’m from Virginia originally. I have always done fine arts my entire life, as long as I can remember. Then, in high school I was introduced to graphic design. I think illustration will always be my first love, and I thought design would be a good route to follow for that. I went to college for graphic design, the program I was in was very print-design oriented. After college, I worked at a pretty small creative agency in Richmond, Virginia. Pretty much within a year of being in the industry there you work with everyone you’re ever going to work with there because it’s just so small. At some point, I visited the Bay Area with some friends. I really liked it and I was like, “At this point I could go to New York or San Francisco, I guess I’ll try San Francisco [chuckles].” I really wanted to live in a big city and NY and SF felt like the only options to me. I also wanted to live far away. I didn’t really understand the implications and impact of moving to the Bay Area. I knew that “tech” was happening but I was very isolated from the culture of tech. I didn’t know anyone in tech but I guess that’s really my bad for being naïve and not doing my research. By the time I was in it, it was too late. I was like, “Oh, shit. I’ve spent so much time and energy breaking into this new industry and now I’m in this industry that’s really problematic.” Not that any of the other ones are any better, but, I don’t know, if you want to be doing big work, I feel like in design, tech is where you want to be. That’s how I guess I ended up where I am at now. It’s not to say that I don’t like tech, I really like designing and illustrating for screens and tech brands but the culture around it is so toxic.

“I knew that ‘tech’ was happening but I was very isolated from the culture of tech. I didn’t know anyone in tech but I guess that’s really my bad for being naïve and not doing my research. By the time I was in it, it was too late.”

I definitely want to dig into that with you. I’m curious, as someone who also grew up in a small town in the south, what it was like for you growing up? Especially as someone who eventually came out as queer?

My dad was a pastor. I grew up going to Christian school. I had to go to church every Sunday and Sunday school with all the youth groups and mission trips. I was really heavily involved in the Christian community and lifestyle. My parents really threw me into it when I was super young and continued to make me participate as I got older. When I was younger it was the only thing I really knew, all my friends were in the church, it was my whole life. I went to this school where they told us your skirts have to be a certain length so you don’t distract the boys in the class and all that kind of stuff. It was super conservative and old school.

I really hated it and I became really disenchanted in middle school and high school, and I think I absolutely carry that with me as an adult, I really have a chip on my shoulder. I don’t know, ideally I wouldn’t have come out in my twenties, but I just internalized so much of the queer-phobia and homophobia around me that it was just for me not a possibility at all. I was in denial and really “othered” anyone queer I ever knew. I mentally categorized queerness as a perversion as a young child as a result of what I was being taught and that really stuck with me. Then when I lived in a small town called Roanoke. This is like southwest Virginia.

“Ideally I wouldn’t have come out in my twenties, but I just internalized so much of the queer-phobia and homophobia around me that it was just for me not a possibility at all. I was in denial and really ‘othered’ anyone queer I ever knew. I mentally categorized queerness as a perversion as a young child as a result of what I was being taught and that really stuck with me.”

So Roanoke is like, I mean, there’s a lot of nice things about it, but there’s a lot of pretty shitty conservative culture there. Once I got to Richmond it was better, but it’s still like, I don’t know, people there are not forward thinking at all. Richmond is better but it’s still pretty bad there too. So I feel like I didn’t really get to make my escape ’til I got outside that area, I think.

So what was it like first getting here? What were your expectations of Silicon Valley?

I think I was pretty naive about Silicon Valley. I had never been. No one around me did anything in tech, and in college my program was very focused on print design. I spent a lot of time making print mocks and doing book crafts. I didn’t even have anyone in my life who knew anything about it. So I think that I came out not really having any idea, and being kind of optimistic, and like, “Oh, it’s a cool environment to work in. It’s fun, it has all these opportunities.” So I think that’s what I thought to be the case. And obviously there are a lot of opportunities, and there are fun environments sometimes, but yeah, I had no idea that it’s ripping San Francisco apart. The community and people, and it’s such an intense rift here. So I didn’t know that, and I was basically getting into tech around the same time I was coming out. So I was meeting all these queer people, and building that community, and they all really hate tech. So I feel like every time I meet a new queer person, I have to come out about working in tech. It’s super strange, it’s like existing in two different worlds, and I had no idea it would be like that. And they’re upset, and rightly so. A lot of my friends are getting displaced, it’s really weird. I just had no idea [laughter].

“I was basically getting into tech around the same time I was coming out. So I was meeting all these queer people, and building that community, and they all really hate tech. So I feel like every time I meet a new queer person, I have to come out about working in tech. It’s super strange, it’s like existing in two different worlds, and I had no idea it would be like that. And they’re upset, and rightly so. A lot of my friends are getting displaced, it’s really weird.”

What excites you about tech, and what activates you work-wise?

There is a lot of opportunity in tech. I consider myself to be a pretty hungry and ambitious person to make change, and do things that affect people. I think that has always been exciting. I also feel like it’s happening, and I can either avoid it or I can ride the wave, and do good for myself and try to make the space less toxic. I mean tech is happening and I really believe that technology can save lives and do incredible things, but unfortunately a lot of tech companies are focused on solving rich people problems. I just want to be around when the focus switches.

“Tech is happening and I really believe that technology can save lives and do incredible things, but unfortunately a lot of tech companies are focused on solving rich people problems. I just want to be around when the focus switches.”

Okay, let’s go into the dark side. What have been some of the biggest struggles for you?

Yeah, I was hesitant about this interview, because I feel like I have some more bad things to say than I do good things, unfortunately.

It’s okay.

Yeah, bad things. It just feels like, in office environments I’ve made a conscious effort to try to make the workplace safe. Safe for myself and safe for other people, and it just feels like an uphill battle. And I feel like I really want to be someone who’s being active about things and calling people out for problematic behavior. But that’s really exhausting, and so then when I don’t do that, I just feel like I’m internalizing all these bad feelings. It’s pretty soul-sucking. For me it’s really toxic for my mental and emotional health. It’s very bro-y. I walk around and see women getting interrupted and being shut down, and all sorts of people feeling shut down.

It’s these people coming from other cities and they went to some Ivy League school and they immediately get a job. They don’t have any sort of idea of the privilege that they have and all of the sudden they have so much money. It feels like college. All these people live in these fancy apartments right where they work and they’re all best friends. All of a sudden they’re planted in the heart of a community that is experiencing violent gentrification and they just step around its citizens and order fancy food from an app to their apartment. And they don’t even have to really go outside ever. I was having a conversation with someone from San Francisco one time and they said that in San Francisco, life really happens on the streets, and if you’re never on the streets how can you possibly respect that? I feel like that’s really true. It’s just weird. It’s really like it feels like a sci-fi novel sometimes.

“I feel like I really want to be someone who’s being active about things and calling people out for problematic behavior. But that’s really exhausting, and so then when I don’t do that, I just feel like I’m internalizing all these bad feelings. It’s pretty soul-sucking. For me it’s really toxic for my mental and emotional health. It’s very bro-y. I walk around and see women getting interrupted and being shut down, and all sorts of people feeling shut down.”

You’ve kind of touched on this a little bit, but what’s it like being queer and working in tech and straddling those two worlds, one of privilege and one underrepresented?

It’s really weird. I feel in a way out of place in both environments. I actually met someone at work and we ended up dating. And we were dating very obviously for a while. And people were just like, “Besties.” And they just did not at all see it as a relationship. And beyond that with a lot of my friends, like I said, I’ve known people to get displaced. A lot of my good friends are social workers and artists, it’s just an entirely different experience. So, it’s super weird. I feel like I have to be really careful and intentional in how to talk about my work in my queer community. And I have to be really careful and intentional about how I talk about my queer community at work, because people don’t understand it. I end up doing a lot of educating to folks in tech. I have many times become the point of contact for trans and queer issues. Or rather, cis/het people having issues with queer and trans folks. People will just throw their confusion at me, and it’s not typically malicious but they just expect me to explain all queer/trans experiences. I’m not even trans… but people will be like “I know this trans person, why did they do this thing I don’t understand?” I don’t know every trans person and even if I did, no one owes you an explanation. I am definitely happy to educate people most of the time but folks so frequently aren’t even respectful of my time or the fact that I may be feeling tired or burnt out that day.

Only share what you’re comfortable with. But, can you share more about your experience with anxiety and PTSD in the workplace?

So, that’s something that is really hard for me to deal with. I think there’s a bigger problem with just the conversation around mental illness and mental health in America. I’ve had so many days where I’m just having a really bad anxiety day. I call in sick. I’m allowed to do that. But then I feel like I have to lie, you know? Because for some reason I feel like I’m not allowed to say, “I had really horrible nightmares all night. I’m exhausted. I need to think about myself, do some art, and then chill out.” I’m always like, “I have a cold. I have food poisoning,” or something. To have to lie about things like anxiety and PTSD, things that are already shameful or shame-inducing for me personally, and I think for a lot of people it’s just this big shame spiral. It feels really inauthentic to talk about it like that. That’s always really tough for me. And I know for a fact that a lot of tech offices and companies are taking really intense initiatives to promote physical health. They encourage people to take sick days for the flu, to genuinely rest and recover. I’ve never heard anyone encourage mental health days. I mean vacation is one thing, everyone needs a break but there is a special kind of rest and retreat needed for folks with mental illness and no one talks about that. I don’t know.

“To have to lie about things like anxiety and PTSD, things that are already shameful or shame-inducing for me personally, and I think for a lot of people it’s just this big shame spiral. It feels really inauthentic to talk about it like that. That’s always really tough for me. And I know for a fact that a lot of tech offices and companies are taking really intense initiatives to promote physical health. They encourage people to take sick days for the flu, to genuinely rest and recover. I’ve never heard anyone encourage mental health days. I mean vacation is one thing, everyone needs a break but there is a special kind of rest and retreat needed for folks with mental illness and no one talks about that.”

Getting to work in San Francisco and being in an office with a bunch of people, and particularly men, make me very anxious.  I don’t know. I’m super jumpy, and people will tap me on the shoulder to tell me something, and pretty much nine times out of ten, I jump. That’s just part of my anxiety and my trauma. And always people are like: “Oh, [chuckles] didn’t mean to scare you.” I mean, people think it’s kind of funny that I’m jumpy. I guess I understand that, but at the same time, I don’t know. That’s really grating, and that’s really hard, and it’s frustrating that people won’t see that and maybe understand to approach me in a different way. I know it’s ridiculous, but if someone jumps up, if someone startles me, I get really, really freaked out.

People have intentionally startled me as a joke. For me, most days are struggling with a sort of ongoing fight or flight response. That’s what my brain feels like. Of course I’m jumpy. I’ve asked people to be respectful about it and some people are really great and other people… just don’t listen. So then I have to sort of consider outing myself as someone who struggles with this stuff. Like, will someone be more respectful if they understand I’m struggling with PTSD? Maybe I don’t want to talk about it. Maybe I don’t trust this person with that information. It’s frustrating that I’m put into this situation instead of someone just respecting my request in the first place.

Little things like that, I don’t know. Not knowing how to address these stigmas in the workplace has been something that’s caused me to really back out and internalize this. And it manifests in a pretty bad way. Actually, Riggins (my dog) is my emotional support animal. He’s been my little anxiety helper. So, he’s really great. I would like to bring him to the workplace. And I know a lot of offices are dog-friendly, but some aren’t. I think there could just be a lot more accommodations for people struggling with mental illness.

Knowing that this interview will launch after you quit your full-time job job, what was the thought process behind leaving to go freelance?

Specifically what happened was I came back from Christmas break and I was like, “I’m great. I’m feeling so good.” I went back in the office and I was like, “Oh, this is bumming me out.” So I got in touch with Ryan Putnam to see if he had any tips or anything. He was like, “Oh, you should come work with me.” Basically the timing worked out really well, but more specifically as a contractor and a freelancer, people are much more intentional with your time. For example, if you’re a full-time designer, you’re probably going to end up designing ads every day regardless of how experienced you are. And I’m like “I don’t want to do ads. I want to be illustrating.” So that’s something that I’m looking forward to, having my time being more valued, specifically. And also, I just want more flexibility. I’d rather be home more.

I will say, as someone who is now freelance, it is amazing to have control of your time, and who you work with, and what you choose to get better at. As long as you’ve figured out how to first create a savings account. Once you have a little bit of savings, then it’s good. At first, it’s really scary. But then it’s like the most wonderful decision you’ve ever made.

I’m starting this. I don’t know what is going on, but I’m not worried about it at all, for the most part. I’m just sort of letting it set over me and I’ll figure it out. I will be okay. And it just sort of creates this nirvana that I’m ready for. I’d rather take the uncertainty and the control over my time and my life.

Have you found mentors, or people you’ve looked up to for inspiration?

I think that I’m still finding that. Working right now with Ryan Putnam has been great because he has shared a lot of wisdom with me. It’s really nice working with him because I feel like he has been really successful as an emotionally aware and vulnerable person as opposed to shouting the loudest. It’s really nice to see that work out well for someone.

What are your biggest motivators, like, what do you think drives you?

I don’t know that I really know how to do anything else. Illustration is all that I really want to do. Sometimes I think about what it would be like if I went in a different direction with my career and I don’t even know what that would look like.

Yeah, I mean, it’s definitely tough as a creative who wants to make art that feeds your soul but also has to survive financially. That’s hard to do in this city.

Yeah. It’s really tricky. I definitely do a lot of fine art on the side, but I still really enjoy the visual design that I’m doing. And it is really nice to be doing what you love for money. It’s like the ultimate hustle, I really enjoy it.

How do your friends and family from home feel about how far you’ve come, and the work that you’ve done, and how you’ve turned out? How does your pastor father feel?

[chuckles] They’re actually really supportive. They have come a long, long way. They voted for George W. Bush, and now they’re voting for Bernie Sanders.

Really?

Yeah. It was a big change. I mean, when we were growing up, at some point when we were kids, my little sister was diagnosed with epilepsy, and they really, really had to fight to get her health insurance. So, they started to see the light of socialism [chuckles]. And that was kind of the tipping point. And then over the years I’ve just seen them grow. I mean, they’re still the same people, but they think really, really differently now. So yeah, I came out to them, and they have been really great and supportive. I get along with them really well. We have a lot of tough talks about their religion, because they’re still Christian, and the things that I believe in. But they are supportive and we get along really well. My mom sends me job listings that are in New York. She wants me to be on the east coast again. They really want me to come back and I don’t think I’m going to go, ever hopefully [chuckles], but it’s really nice to have their support.

That’s really great.

Yeah, it’s nice.

How do you feel about the state of tech in 2016? How have you seen it change in your short time here? What is exciting? What is frustrating? What do you want to see change?

Why do I feel bad now? I personally feel really, really, very torn about it. As much as I am in the camp of tech is happening, whether or not you’re in it. There’s all these ridiculous apps that get funding and fall through. It’s super weird. I don’t know. I see some good efforts happening and I see also really shitty things. I have a few friends in tech who are women and they have had okay to awful experiences. So I don’t know. I feel not too optimistic at this point. I think that the whole culture needs to shift for any of this to actually be sustainable work. I think the only reason I’m going to be freelancing with tech companies, and the reason I’m continue to freelance with tech companies is because I kind of do it on my own terms, and I think you have to make it work for you, for it to work. But I really hope that it changes, I just want it to be a safe place for people like that. So, not optimistic.

How do you think tech could be more accommodating to folks who are suffering from PTSD or anxiety, or other mental health issues, just based on your own experience?

Yeah, it’s a great question. I think just being able to talk about it. I think that it seems so much of work, even at happy hours, people are talking about work. I think that bringing some shift of people being willing to talk about what’s really going on with them. I just think that mental wellness puts me at my best in the workplace. People are working long hours and it’s demanding work, and I think companies need to create structures and places for people to be able to talk about that.  I think if companies are willing to talk about, it would sort of open the floodgates for people to be able to talk about their own experiences and make it easier. I think just facilitating where to talk about it.

Where do you see yourself in five or ten years?

I would like to be able to get over my fomo enough to move somewhere that’s a little less intense than the Bay area. I don’t know. I think like, ideally, I see myself freelancing or working with like a small dedicated group of really rad designers or creative people. I don’t really see myself in any tech companies.

What about 2016, are you working on any projects either for work obviously building your freelance business, but like personal goals or anything like that?

I’m taking a break from doing artwork outside of work. So I think my focus right now is to do my work and then focus on some more of my crafty hobbies. So nothing big coming up, no projects. I think this year I want to learn how to garden and I’m going to learn how to do woodworking. Those are my very chill goals.

I’m all about it. Learn how to not work for a minute [chuckles], it is its own discipline. Let’s see, my last question for you would be, what advice would you give to folks from similar backgrounds or who have gone through similar struggles, and are getting started in tech?

I know we talked about mentors. I think what’s more important than mentorship or anything like that, and what’s always been more helpful to me, is finding peers and building your community. Just finding other women at work, or finding them outside of work, and really building that community to go back to and have a safe space. I think it is super important. I think at the end of the day, if you’re struggling with something, or having a bad day, or wanting more overtime, I think the most important thing to always remember is you are number one, the company isn’t. It’s so important to focus on yourself and not lose yourself in the noise that is all of this stuff. I think that those two things have really been what’s kept me going.

“I think at the end of the day, if you’re struggling with something, or having a bad day, or wanting more overtime, I think the most important thing to always remember is you are number one, the company isn’t. It’s so important to focus on yourself and not lose yourself in the noise that is all of this stuff.”

I used to be resentful about growing up in Connecticut, but as I get older, I think I become more and more Connecticut-y. It was a very Puritan, affluent, seat-of-the-American-Revolution type of town, and my siblings and I were the token Asian kids in all of our classes. This one time in history class, we were talking about Charlemagne or something, and the teacher said, “Did you know that everyone of European descent is actually related to Charlemagne?” And everyone in the class just turned around and looked at me. So unsurprisingly, I didn’t really feel like a part of the community.

My parents both worked. I didn’t really think anything of it when I was growing up, but I had a lot of time to myself. There was this expectation from my parents: “We’re not going to entertain you. You have to entertain yourself. Go to school and get good grades. Do your own thing.” I drew a lot, wrote little stories, all the kid things. In high school, I was super into smudgy digital paintings of fantasy things and making weird emo websites.

“My siblings and I were the token Asian kids in all of our classes. This one time in history class, we were talking about Charlemagne or something, and the teacher said, “Did you know that everyone of European descent is actually related to Charlemagne?” And everyone in the class just turned around and looked at me. So unsurprisingly, I didn’t really feel like a part of the community.”

When did you first get really interested in tech? Or did you not get interested until you were kind of in it?

I was always into it, I think, but I didn’t know it. My dad encouraged me to code sites. When I was 11 or 12 I was making Neopets fansites and things like that. In high school I had this realization that it wasn’t something girls were ‘supposed’ to do. There was this message floating around, “you’re a geek girl. You built your own computer.” I just did it for fun. From there I thought, “well, I must be a tomboy,” and that became part of my identity. In retrospect it’s very disturbing. “I’m a non-girl. I don’t have girl friends. I’m one of the guys. I am literally not a woman, because women don’t build things.” I didn’t realize how problematic this was until I was in my twenties.

From there, I went to Carnegie Mellon’s design school, which was great. We had a lot of female professors that we respected and my class had a good mix of genders and at least some diversity.

“My dad encouraged me to code sites. When I was 11 or 12 I was making Neopets fansites and things like that. In high school I had this realization that it wasn’t something girls were ‘supposed’ to do. There was this message floating around, ‘you’re a geek girl. You built your own computer.’ I just did it for fun. From there I thought, “well, I must be a tomboy,” and that became part of my identity. In retrospect it’s very disturbing. ‘I’m a non-girl. I don’t have girl friends. I’m one of the guys. I am literally not a woman, because women don’t build things.’ I didn’t realize how problematic this was until I was in my twenties.”

So from there you started in advertising?

I did. Advertising is a weird beast.

Yeah, I have friends who have transitioned from ads to tech, too. They told me about the ad years, which sound way rougher, honestly.

I think everything is just less hidden. I think things are more, “welp! It’s going to be like this, and that’s the way it is!” There’s some truth to the Mad Men stereotype, the glorification, the partying, using client dollars and working yourself into a stupor.

Yeah. I think I saw in the news—a girl in Singapore that worked three days straight and died of heart failure. She was like 20, you know, a copywriter.

It’s so not worth it. But you think, this is what I have to do to get ahead.

Walk me through the path from agency to tech to independence.

In short, I saw what they charged for me and what they were paying me. This was probably true at any creative agency of that era. Not only were they paying me a quarter of what they were charging for me, but they were also lying about there being x numbers of designers on the project. It was just me. I thought, maybe I should just do this on my own, even if I can get only a few clients. If I charged half of what they were charging, I could make a living. At that point, I wasn’t used to making a ton of money anyway.

I graduated during the recession, so I know what it’s like not to be able to get a job. I sent out over sixty applications trying to get my first gig, and only ended up getting requests to interview from two people. This is after attending a great university with a string of internships under my belt. I was ready after graduation to work as a barista or a librarian to move to San Francisco, so I was still up for that as a last resort.

“I saw what they charged for me and what they were paying me. This was probably true at any creative agency of that era. Not only were they paying me a quarter of what they were charging for me, but they were also lying about there being x numbers of designers on the project. It was just me. I thought, maybe I should just do this on my own, even if I can get only a few clients. If I charged half of what they were charging, I could make a living. At that point, I wasn’t used to making a ton of money anyway.”

So this was my first pass at going independent. I had no idea what I was doing, but even with my then-paltry San Francisco connections, I carved out a living.

I was posting on Dribbble a lot, and one day Mark Otto (who was at Twitter at the time) said, “Hey, why don’t you come have lunch?” I still love Twitter and use it a lot. Everyone seemed super nice, and it would be a prestigious place to work, so it checked all the boxes. I stayed for about a year, doing brand and marketing design. The company grew from 500 to 1000 people while I was there, which started to feel too big.

That’s when I started peeking over at Pinterest. It was just 35 people when I joined. What really attracted me was the userbase, which was not a typical techie-first audience. It was people who had jobs outside of Silicon Valley, who lived all across the country, and had families and other aspirations. The ethos of the company felt really homey, where we’d unironically make Valentines for each other. I always wanted to go independent again, but I figured I’d stay at Pinterest for 4 years as my last gig. Then, they grew to 300 people in the space of two years, which was even more stressful than when Twitter grew. I could only take two years of hypergrowth before I had to leave.

“I sent out over sixty applications trying to get my first gig, and only ended up getting requests to interview from two people. This is after attending a great university with a string of internships under my belt.”

I’ve been independent for about two years now.

What are the things that were really exciting that you took away from your time working in-house? And then what was not so great?

I met so many good people working full-time. It’s one of my fantasies to move to the middle of nowhere and have a crazy farm, but it’s hard to leave the Bay Area because I know so many awesome people. I do feel like for all its faults there’s a great community out here, especially a female community, which is something I’ve needed and cherish.

There’s a lot of stuff I didn’t love, too. By the end of my full-time adventures, I was having health problems, things I’d never experienced before. I had full body rashes and new allergies. I was constantly getting sick to the point of being bedridden, and doctors couldn’t figure out what was going on. I don’t have any of these problems today. It’s as if my body was like, nope. You’ve got to chill the fuck out.

Throughout my life, I’ve always wanted to seek creative criticism and wanted to get to the next level, but I never doubted myself. My early 20s and mid-twenties was all doubt, though. When I was leaving full-time work, I was evaluating if I should even stay in design. I was ready to quit the industry, quit being a designer because I’d become convinced that I was not good enough to hack it. I wasn’t producing good work, it was like in sports, I had the yips. It’s really depressing looking back on that era, because I know now that there’s so much out there for me. I’m glad I got out when I did.

“By the end of my full-time adventures, I was having health problems, things I’d never experienced before. I had full body rashes and new allergies. I was constantly getting sick to the point of being bedridden, and doctors couldn’t figure out what was going on. I don’t have any of these problems today. It’s as if my body was like, nope. You’ve got to chill the fuck out.”

I felt similarly in my work in tech, and actually my best friend worked at a big agency where she was an art director, just killing it working on huge global brands. Confidence through the roof, and then she moved to tech, where I met her at my tiny little startup, and I watched our young, inexperienced bosses just destroy her confidence and it’s never really come back even though she’s worked at better and better jobs and does incredible work. And I just still see her not fully believe in her work, even though I’m like “look at what you’re making,” you know? And I’m like, what did tech do to her to make her feel that way?

It’s still a bit of a mystery to me. When I left I had this realization that I was internalizing a lot of things. One example is how old I look. I’m almost 30, but Lyft drivers will ask me if I’m headed to class. A worker at the DMV asked if I was there to take the driving test. I’m sure I’ll be happy about this when I’m older, but it’s easy to feel like my face is betraying me.

I realized it wasn’t my face betraying me, though. It’s my face, it can’t do such a thing. Part of being independent meant I could stop feeling like I was fighting others’ notions of me, that I could stop fighting my own face.

“Throughout my life, I’ve always wanted to seek creative criticism and wanted to get to the next level, but I never doubted myself. My early 20s and mid-twenties was all doubt, though. When I was leaving full-time work, I was evaluating if I should even stay in design. I was ready to quit the industry, quit being a designer because I’d become convinced that I was not good enough to hack it.”

There’s a lot I can’t and wouldn’t change about myself or the way I look, and I want to spend my time solving problems and telling stories, rather than figuring out ways to keep people from being mistaken, offended or threatened by my mere existence. I got so sick of thinking, “Oh, if I dressed exceptionally well (but not too well), people wouldn’t discount my opinions. If I smile the right amount (but not too much); if I use enough emojis in my emails.”

Yeah. You wrote a medium post highlighting some of your experiences in tech, and that resonated with quite a few people, including myself. For those who haven’t read it, who will read this, walk me through some of those experiences.

When I was debating whether or not to leave tech altogether, I was so jaded. I spent about a year being totally burned out. I couldn’t even click on links about “woman sues x for discrimination” or “x scandal” because they would make me so angry. But tech keeps drawing me back in, because of that same attitude I had as a kid, where I didn’t know I was interested in tech. I just wanted to make cool stuff, to express myself, to be heard. Tech is not the point. People are the point, and tech’s supposed to be in service of people. I’m so looking forward to the day when teens are making one-use apps that are like, Beyonce lyrics and things like that. The things we see as deeply technical are going to get more democratic and more accessible until they become as common as shooting off an email. That’s my hope.

In the meantime, I’ve sort of given up the idea that I can succeed in a traditional tech role. I’m sure a job is out there for me, but it’s not going to be in the majority. It doesn’t make much sense for me to look, statistics not being on my side, especially when I can carve out my own business and feel like I have power again.

“Tech is not the point. People are the point, and tech’s supposed to be in service of people.”

I think you can probably relate, where one of my biggest issues was feeling like I didn’t have any runway. And just knowing the work that I could do if I was allowed, and not being able to perform in a way that would have been good for the company. I felt like I was constantly being kept in a box and prevented from helping in significant ways.

It’s like there’s a code you can’t crack. I’d see a problem, see a way forward, a way to get it done. But then I would come up against friction: “You have to do this list of process to get that done.” So, I’d do those things and then the response would be, “You follow the rules too much, why can’t you just take initiative and do it?” So, I’d break the rules, usually emulating male coworkers, and then suddenly I’m branded a troublesome employee. At that point, the game is rigged, isn’t it? There’s no path forward, to the point where I’d ask, “would it be better for me to do nothing?” and I kid you not, the answer was sometimes, “that’s probably for the best.”

This didn’t work for me. I’m genuinely curious if it would work for anyone. I was a very bossy, stubborn child. I was always raising my hand in class in the front row. I was that girl. But after this slow draining, this slow reward after reward for being malleable and feeble, I was becoming one of those people who were averse to conflict for the sake of appearing easy to deal with.

“I’d see a problem, see a way forward, a way to get it done. But then I would come up against friction: ‘You have to do this list of process to get that done.’ So, I’d do those things and then the response would be, ‘You follow the rules too much, why can’t you just take initiative and do it?’ So, I’d break the rules, usually emulating male coworkers, and then suddenly I’m branded a troublesome employee. At that point, the game is rigged, isn’t it? There’s no path forward, to the point where I’d ask, ‘Would it be better for me to do nothing?” and I kid you not, the answer was sometimes, “That’s probably for the best.'”

For you, was it mostly just the sum of a thousand paper cuts? Or was there like a moment when you were like, “Ok. Here’s my plan on getting out.”?

I had this story in my head that I was just an unhappy, ungrateful person. That even if I had the world, I’d still be a grouchy, angry person who wouldn’t be able to sleep at night. It had been building for a while, but I think I woke up one day and thought, this is not sustainable. I have everything, and I’m wasting it. Two generations ago, my family was fleeing war and hiding in haybales, getting bayonetted at by soldiers. For me not to take the leap when I could does nobody honor.

So how much of that has resolved for you working as a freelancer?

It changed so quickly. Of course I had moments where I was insecure, where I worried that no one would want to work with me, where I thought the money would dry up. Instead, I found that there were really loving, enthusiastic people out there who just wanted to make stuff together. It was a revival for me, a restoration of faith. My work immediately improved. It was such a relief.

It’s such a bummer that so many people can go from extremely confident people and end up in an environment where we are turned into people who don’t feel valid whatsoever, end up having to repair it ourselves on our own, and then end up thriving.

It’s a self-fulfilling cycle, when someone says, “I don’t have faith in you.” People would be surprised constantly at my age, my experience, and I realized they were making all of these underlying assumptions about me. There would be people who were like, “Oh, Ash is so sweet.” And I was like, “whoa, that’s an adjective a mother or boyfriend should be using, not you, coworker. Besides, did you not see all the Instagrams I took in the cemetery? All the black I wear?” To undo all those assumptions is a whole ‘nother job.

“It’s such a bummer that so many people can go from extremely confident people and end up in an environment where we are turned into people who don’t feel valid whatsoever, end up having to repair it ourselves on our own, and then end up thriving.”

I had managers call me sweetheart when they weren’t thinking, off the cuff. I’ve had people scold me for writing emails that were not strongly worded in the least. I’ve had people tell me not to go to company sponsored classes because I’d be ‘in over my head,’ that I ‘didn’t have enough experience’, and then I’d see a bunch of men there that were way less experienced at coding than I was. I would have managers not tell me important information because of some virtuous paternalism, and then it would limit my ability to do my job. And that would result in people labeling me incompetent, junior, thinking, “maybe there’s a reason we don’t tell her everything.”

People don’t do it out of malice. Almost all of these people are nice humans, they have families and will smile when you talk to them. It’s just all these assumptions they don’t realize they are making which slowly wear away at women’s reputations.

Did you have any mentors in the industry or people that inspired you on the positive end?

My first job, I worked with a badass art director, Christina Rinaldi. She was my first example of what being a working woman could mean. She was first and foremost a great designer, so creative, but she was short like me and wore heels. She never tried to hide the fact that she was female.

Now I feel fortunate that I’m surrounded by lots of awesome women. My friend Alice Lee uses the term ‘friendtors.’ I have this loving coven around me. I’ve had male mentors as well, which I think is important. I don’t think a lot of men naturally gravitate towards mentoring women, but in this climate it can be hard to find a female mentor.

“I had managers call me sweetheart when they weren’t thinking, off the cuff. I’ve had people scold me for writing emails that were not strongly worded in the least. I’ve had people tell me not to go to company sponsored classes because I’d be ‘in over my head,’ that I ‘didn’t have enough experience’, and then I’d see a bunch of men there that were way less experienced at coding than I was. I would have managers not tell me important information because of some virtuous paternalism, and then it would limit my ability to do my job. And that would result in people labeling me incompetent, junior, thinking, ‘Maybe there’s a reason we don’t tell her everything.’

People don’t do it out of malice. Almost all of these people are nice humans, they have families and will smile when you talk to them. It’s just all these assumptions they don’t realize they are making which slowly wear away at women’s reputations.”

What do your friends and family from home feel about the work that you’ve done?

There are few people I’m friends with from high school still, but I’m in a pretty different place now than I was back then. My parents I think are just pleased I’m self-sufficient. They try to be supportive, but I do think they wonder what I do every day. My dad came to my senior project at school and looked around at our work. He said, “There is some theme here, but I don’t know what it is.”

I’m always curious to know the secret sauce or the common trait that allows people to start their own thing, which is absolutely not what most people want to do. What do you think that is for you?

I can’t say for sure. I’m pretty stubborn, which helps. I think for me, I just want to be free. I want to solve problems and tell stories without all the man-made conflict. There’s a lot of that personality in Silicon Valley, the one that gets a little kick out of debate club, of watching people squirm and setting stuff on proverbial fire. I’ve turned into a giant California hippie. I’m into the idea of cooperation.

I think the other thing is that I’m actually scared and embarrassed most of the time. Like, I have this phobia that my phone is going to bounce into a sewer grate twenty feet away when I’m holding it, I’ve slipped on banana peels and run into glass doors. That constant state of anxiety is a blessing, though, because when I get scared of running my own business, it’s kind of just another fear for the pile.

How do you feel about the state of tech right now?

If someone else tells me tech is a meritocracy, I’m going to fucking scream. I think there’s a lot more awareness that we’re all biased and raised to be racists, even (maybe especially) minorities. And I think the goal of talking about it is to just be more mindful. No need to be perfect, just be aware and try not to do nasty stuff, apologize when you’re hurtful. But some people are still so defensive about it. You can say, “hey, that was kind of misogynist, please don’t say that,” and the response is, “I’m not a misogynist!!” And that totally derails an expression of discomfort into a cosmic, immovable perception of someone’s ego, which was not the point. It’s like saying, “you’re standing on my foot,” and the other person saying, “I’m not fat!”

Wouldn’t you want to be told? I think it’s so ironic, tech is always asking for quantitative affirmation, for data, but the data that says diverse companies do better is ignored. I’m an optimist, though. The way things are going, if you’re going to ignore inclusivity, you’re going to be a dinosaur in a few years and the diverse companies are going to crush you. I guess we’ll see.

“If someone else tells me tech is a meritocracy, I’m going to fucking scream. I think there’s a lot more awareness that we’re all biased and raised to be racists, even (maybe especially) minorities. And I think the goal of talking about it is to just be more mindful. No need to be perfect, just be aware and try not to do nasty stuff, apologize when you’re hurtful. But some people are still so defensive about it.

Wouldn’t you want to be told? I think it’s so ironic, tech is always asking for quantitative affirmation, for data, but the data that says diverse companies do better is ignored. I’m an optimist, though. The way things are going, if you’re going to ignore inclusivity, you’re going to be a dinosaur in a few years and the diverse companies are going to crush you.”

You left the industry as did I. There is so much conversation around pipeline, but not many people talk about retention. What do you think tech could do to not lose more talent?

That’s a hard one, because the only way I could figure out how to work in tech and not have my creativity destroyed was to exist on the fringes. Number one, we need more diverse founders. I saw some sad statistic recently that women founded companies make up a single-digit percentage of companies funded here. There are plenty of female entrepreneurs who don’t do things tech finds glamorous: fashion bloggers, YouTube stars, self-help gurus. So the idea that this is a meritocracy and that women just aren’t interested in being entrepreneurial is ridiculous.

I think we also need to put our monies where our mouths are and be open to criticism and dialogue. Again, it’s just so deeply ironic—people will seek out user feedback and try to get people to bash their apps so they can improve them, but then shrug off any critique on how their company about page is a wall of young white men.

The other thing I’m doing right now that feels more subversive is making things for the female gaze rather than the male gaze. So not everything has to be a stoic flag on a hill. Just be better humans day to day, or try to be.

Have you seen your personality change since you went independent?

Yeah, I feel more like myself. Now if I don’t want to do something, I’m pretty clear about it, to the point where I’ll surprise myself. Like, I didn’t know I had an opinion on that! I don’t put 3 emoticons in every single email. I still put them in because I like them and think they’re funny, but not to seem cute or innocuous. I’m a lot better with boundaries, I won’t check email on weekends—well, I shouldn’t say never; sometimes it’s necessary, but if so, someone’s going to pay Oprah dollars for that time.

Honestly I feel 10 years younger.

People see me and they say, you look great. I’m just like, God, what did I look like before?

Covered in rashes.

Blotchy and sad.

Where do you see yourself in 5 or 10 years?

I’m really enjoying my life right now. I would love to get to a place where I’m doing only independent projects of all kinds. I’ve always been one of those people who’s been interested in 20 things at once, which I think is sometimes punished in full-time work. “Oh, you’re erratic, you can’t focus.” And it’s less about focus than multi-tasking. I want to build apps, I want to keep publishing books, and it all seems possible.

What advice would you give folks who have had similar experiences to you in tech or even just girls hoping to get into tech?

That’s a big one. One thing is that most of the women I know have gone through this deep experience, almost a second, older adolescence where they figure out what they actually want, versus what they are told is desirable. Everyone was pushing me into management. I did not want to stop making things, but people would say, “oh, you have a caring air about you,” and other bullshit like that, or get overly excited if I said I wanted to mentor someone in the company. I think people are very quick to tell women what they want and shouldn’t want. Taking the time to outline what it is you as an individual want is so important. It will probably confuse people (when I left Pinterest, some random guy I knew in high school literally commented “noooooooo!” on my announcement) but if you know it’s what you want, it won’t bother you so much.

“Most of the women I know have gone through this deep experience, almost a second, older adolescence where they figure out what they actually want, versus what they are told is desirable. I think people are very quick to tell women what they want and shouldn’t want. Taking the time to outline what it is you as an individual want is so important.”

I was born and raised in Cupertino, CA. My parents are both from China, and immigrated here in their mid-20s, so growing up, I spent many summer vacations with my extended family in China.

What was family life like? What did your family expect of your career-wise? What did you think you were going to be when you grew up?

My parents are my ultimate heroes in life, and there is no way I can possibly overstate that. They immigrated here from China in the 80s, barely speaking the language and having just finished graduate school. When I was 10, they founded their own individual biotech companies, both as solo founders. They went up against crazy challenges and a language barrier, yet eventually led one to acquisition and one to IPO. As a kid, “growing up” alongside both of their ventures and witnessing the sheer force of their perseverance and hard work became one of my biggest sources of personal inspiration.

When I was younger I had no idea that I would go into the arts, but I always knew that whatever I ended up doing would have some element of entrepreneurship involved. Also, I’ve learned a lot about the value of demonstrating to your kids the importance of hard work and passion for what you do (whether that’s in your work or the values with which you live your life).

Honestly, when I am going through something challenging in my career I think about my parents, and how they came here with few resources, little knowledge of the language or how American society here even functions — and were still able to grow their initial visions into two multi-national companies today. And then I just think, if they can do it, I can do this too. 

To me, they are the true embodiment of the American Dream: immigrants who, through extremely hard work and perseverance, have found success on their own terms. 

How did you first get interested in tech and design?

I’ve always been interested in design, but that was before I knew it was “called” design. When I was younger I’d delight in figuring out systems to make processes more efficient. I went to business school at the University of Pennsylvania’s Wharton School, and my major there was a business-related take on that (Operations & Management). I got into design on my own, taking on internships that were on the business and platform sides, and studying from the designers in my spare time. I’d offer to take on extra projects that weren’t necessarily high priority for them, and in turn I ended up learning a lot about what it takes to ship a product.

How’d you end up in SF and in tech?

I’d been interested in tech throughout college, taking on internships at Microsoft, Foursquare and Path, so it was something I wanted to continue afterwards. I’d always wanted to come back to SF after graduating from college because this is where I grew up. The fact that the tech industry has been in an upswing and was in an extremely optimistic place in 2012 helped too!

What were your first impressions of Silicon Valley?

I had a very positive initial impression of Silicon Valley, partly because I grew up here and a lot of it feels very natural and organically “at home” to me.

It’s funny because often people here will refer to a particular location or “Bay Area thing” in a certain context, and for me it’ll always have specific connotations to high school and whatnot. For instance, sometimes after telling someone that I grew up in Cupertino, people will be like “Oh my gosh! What is it like there? Is it really cool?” and my answer is “Haha! It’s actually really boring.” Or, someone will ask if I want to meet at a certain coffee shop in Palo Alto, and that’s where I remember cramming for my SATs because I did all of my standardized testing at either Palo Alto or Gunn High Schools.

What was the impetus for leaving to go freelance?

There were many reasons but one thing that appealed to me more than going to work for a company was the idea that I could try out a lot of different things within the general world of illustration and art, and have that count as being part of my career. In the same vein I think that independent life is a particularly great option for people who have a lot of different interests that they want to combine in their professional lives.

For instance, one day I’ll be painting a 10×10 ft mural for Slack, and the next I’ll be lettering on a home goods project for Macy’s, and the next week I could be drawing an inventory of in-app product illustrations for Wealthfront. I also do a lot of personal experimentation and am starting to branch into some gallery work, which is extremely rewarding in its own way. It’s a really fun mix and I feel like I would not nearly have grown as much both technically as an artist/draftsman, nor would I be as strong a conceptual thinker had I stayed in one context. Those are qualities that I care about optimizing to the max at this point in my life and career.

What has your experience been like as a freelancer?

My experience has been extremely positive, empowering, and affirming. It is really exciting to constantly feel like I am creating my best work and then see that shipped, live, and in context of a client’s project. I tend to be pretty particular about the projects that I take on, and my clients so far have all been truly wonderful people to collaborate with!

In general, how has your experience been as a woman in tech?

I think a lot of the discrimination that women in tech face is extremely subtle – death by a million paper cuts. I feel the need to be extremely aware of where and who I’m working with because at the end of the day, I really do believe that the values of the industry at large do not include much empathy for people who don’t belong to the “default” identity (ie. white, CIS male, not an immigrant), and if I don’t do this for myself, then no one – not an HR department or my manager – will do so for me. I have really little faith in “things working themselves out” in this industry context unless I proactively look out for myself, and I see tech as one of many industries that I work within as an illustration (ie. from editorial, retail, to broader advertising), rather than a core piece of my identity.

In some ways, it’s somewhat analogous to my parents’ journey as CEOs in the US who immigrated here from another country. They encountered a lot of discrimination, both overt and subtle, especially given that their identity wasn’t accepted as the “default” identity of success (aka white, male, no accent) in our Western society. Perhaps certain things may have come more easily or directly to them had they belonged to that default identity, but I deeply admire their drive in carving out their own extremely unique paths to success that I think greatly trumps what the default path could have given them.

Have you had mentors or people you’ve looked up to for inspiration along the way?

Yes, many of them have been people I’ve gotten to work with (ie. Ryan Putnam, Morgan Knutson, Allison House, etc), and recently I’ve started more official mentorship relationships with illustrators who work in the publishing and advertising industries. I think it’s cool to learn with people who come from a variety of different backgrounds!

What are your biggest motivators?

All I can do in life is try my best.

I also tend to get really inspired by others and their bodies of work; for instance I’m really digging Japanese director Makoto Shinkai’s work right now and I’ve been practicing how to paint in his style. So I think having a lot of true, from-the-heart inspirations of older practicing artists (from the general art/illustration communities, not necessarily tech itself) has been extremely motivating for me.

Where have you found support networks?

I’ve found amazing support networks just in friends as well as this social Slack channel that I’m a part of that Justin Edmund started (designer, formerly at Pinterest, first designer there). It’s a really cool group of people that I would broadly classify as individuals who consider themselves “makers” (ie. designers, engineers, illustrators, writers, founders, etc) and it’s a great place where we’ve been able to talk freely about things that I’d otherwise feel really vulnerable talking about “in public.”

What do you look for in a job now vs. when you started?

I look for a lot of similar things (product and mission that I’m passionate about, solid business plan + trajectory, strong leadership, strong presence of design in the org, etc), but the difference is that now I look for more things like:

What are the HR practices in place to deal with workplace issues? Are there HR processes at all?

How empathetic do the founders, early members, and leadership appear to be?

Inclusion: Are there women in positions of leadership? Is there a woman in a position close to the role that I will be taking who I can potentially talk to? What are the gender and broader diversity ratios in place, especially on the technical side (where I spend most of my time)?

How do you think your background and life experiences impact the way you approach your work?

I think my self-taught path from business school to illustrator who draws and paints professionally has unexpectedly resulted in an interesting pairing between business and art.

So what are you working on right now, either for work or for yourself?

Right now I work with a bunch of companies like Slack, Wealthfront, Macy’s, etc. as well as smaller startups in the tech industry. I’ve also worked on a range of really cool projects, from editorial (ie. New York Times) to animation (Tonko House).

I also love painting and drawing, and this year have started to show as part of gallery shows (Q Pop, Light Grey Art Lab, etc).

Where do you see yourself in 5 or 10 years? Do you think you’ll stay in tech?

Professionally, I see myself expanding into different industries (ie. not just tech, but also publishing, editorial, advertising, etc). Personally, I would like to be more established as an artist and find more of my individual voice. I think I’ll continue to work in tech but my priority right now is to maximize my technical ability as an artist.

What advice would you give to folks from similar backgrounds who are in tech or hoping to get into it?

It’s kind of hard for me to answer this question, because everyone’s experiences are so different. Seeking out mentors, aligning yourself with a company that wants to invest in young talent, and trying to figure out ways to reverse engineer projects and skills are very actionable steps that you can take to grow on your own (in the beginning, at least!).

At the end of the day, all I can do is try, and try my best. Sometimes there are things that get in the way that are beyond your control, but I really believe that where there’s a will, there’s a way. That’s something that my parents’ experiences have taught me too; observing their hard work and optimism through their respective paths became a really ingrained lesson from my childhood.