So, let’s start at the beginning. Tell me about your early years and where you come from.

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.”