Apple Editor Turned Artist


Windy Chien is many things. Not only is she an artist, she’s a tech consultant, music expert, and teacher, and much more. Nowadays, she creates stunning fine art out of her airy studio in the Mission District of San Francisco. As an Asian American breaking into the indie rock and punk music scene, or a woman diving in the world of male-dominated world of tech, Windy doesn’t let being an outsider stop her.

“I really absorbed the feminist lessons of the 70s, and lessons of America— that you can be whatever you want.”

Full audio interview with Windy will be up soon.

Rather, she has taken the opportunity of being an outsider to self-define and create her own path in the world. We recently sat down to chat with her about how she made multiple career jumps in her life, what it’s like being an outsider, and her art work, and more.


A trailer for our talk with Windy Chien.


by Nanette Wong

Photos by Nanette Wong. Video by George Ko

GR: Tell us more about your three lives. How did you successfully transition from independent record store owner to App store editor to fine artist?

W: I like to say that I’ve lived three lives already, and to me that’s very comfortable. I think it’s natural for me because I want to experience all that life has to offer. I first moved to San Francisco in the 90s, which was the pre-ipod, pre-digital music age. If you were into music, the first place you’d visit is the record store. That’s where you’d meet all your new friends, learn about what shows were going on, and where you could read about music. I’ve always been drawn to what’s happening in the moment, and I first began working in record stores. Then, I came to own my own independent music store, Aquarius Records, that I moved from Noe Valley to Valencia Street in the Mission. I did it for 14 years. By the end of 14 years, I wasn’t unhappy, but I wanted to know how the rest of the world lived. It was really hard to leave because my whole identity was Aquarius Records. It was really hard to leave that identity, and that kept me there a little longer than I should’ve been there.

When I finally left, I took a year off, then eventually found Apple. Music was the connector there— it was the early days of iTunes. I helped build up it up to the store we know it is today. When I first started there, it was only a US music store. I was there for the next five years of explosive growth, adding movies, iTunes U, iBooks, and eventually the birth of the App Store. Then, we expanded to 140 territories around the world. I jumped to the App Store, where I built and managed the Editorial Team. I did that for three years.

After eight years at Apple, I was increasingly becoming very envious of other people’s creativity. I began to realize that my entire career at Apple and at the record store, was in a way, about supporting other people’s creativity. By that time, I was in my mid-40s, and I realized, I just want it to be all about me, me, me, and my own creativity.

And I felt like I earned it.

By that time, I was in my mid-40s, and I realized, I just want it to be all about me, me, me, and my own creativity. And I felt like I earned it.

So I took the leap. Again, it was hard, not because I was leaving my identity, but leaving security— the fancy job, the approval of my parents. Leaving the safety net. But I did it, and it was a really great decision. I took a year off, frantically trying to figure out what I was going to do next, and it took awhile for me to relax and let it happen. But eventually, it did. And out of all the different art forms I tried, the ones that really stuck were wood carving and rope. I started out with a very traditional form of macramé, then quickly decided that the few knots that macramé artists used were very limiting. I started learning more and more knots, and then more and more knots. That’s what led to my Project, The Year of Knots, and everything’s been great since then.


GR: What’s your advice for those who are interesting in taking a daunting leap of faith?

I feel like our parents, especially our Asian parents, would always focus on the worst case scenario. What I’ve discovered now, about three years into doing the art and after leaving Apple, if you work hard and you’re pretty smart, you’re probably going to be fine. You’re not going to be worst case scenario.

W:It’s also important to have a safety net, but it doesn’t have to be huge. All you need is enough money to pay rent and a bit to eat. Set aside enough money for your living expenses for ___ months. You decide how many months. Why this is genius is because you’re making this decision once, rather than once every month. You don’t have think at the end of every month, do I have enough money for rent or food for another month? You’re taken care of for x amount of time, and you don’t have to worry about it. Then you’re free to hear the voices inside of you telling you want you want to do for the rest of your life.

On knowing when it’s time to take the leap— I think that when the impulse to try something else or change becomes strong enough, you’ll know. If it’s not that strong yet, then it’s probably not time.

On knowing when it’s time to take the leap— I think that when the impulse to try something else or change becomes strong enough, you’ll know. If it’s not that strong yet, then it’s probably not time.

GR: Which transition was harder? Leaving Aquarius or leaving Apple?

W: The first one was harder. By the time I had transitioned out of Apple, I already experienced leaving an identity or major phase of your life. By the second time I did it, I knew I was going to be fine.


GR: How has being an Asian American affected you/your work/you art? If it affected them at all?

W: Being an Asian American, I’ve always felt like an outsider. Being an Army brat, I grew up all over the US— from New York to Colorado to Georgia to Hawaii. Growing up, I was always the only Asian kid around until I moved to Hawaii. I’ve always felt like an outsider, being Asian American, and as a kid growing up in the United States, you get used to being that role. Then it’s up to you to either grab it by both hands and run with it, or be damaged or bitter. There’s a myriad of reactions you can have towards feeling like an outsider.

But to me, my outsider status has worked. The perspective that you take being an outsider is very comfortable to me. I like being on the outside. You get to self define. When you’re a black sheep, or when people don’t know what to do with you, you get to self define and that can be a blessing. It can be freeing.

GR: What is your creative process like?

W: Most of my large scale work is improvised. I often get ideas first and sketch them on paper, but you often don’t know how something is going to look until you actually make it and experiment. And nine times out of ten it’s not that exciting. But one time out of ten, you make it, and it has this pulsating life to it and that’s when you know— I’m going to keep making this.


GR: What does a day in your life look like?

W: My day typically starts with doing some admin work in the morning. I head into the studio around 11am. First thing I do is make a knot— get my hands working immediately, which gets me into that state of flow and gets the creative juices flowing. Now that I’m not making a brand new one everyday, I still like to get my hands moving doing something small. Then I get going on a big project, by continuing one or sketching out a new one. I spend all day here in the studio, then leave around 6 or 7. I usually work one weekend day.

GR: What’s next for you?

W: I would like to break into the fine art world, understanding it and experiencing it. Mainly because I like exploring new worlds. That’s why I’ve had three phases in my life. I’m super fascinated to see what the fine art world is like, and do it on my own terms and figure it out. A show at a proper art gallery, which is already scheduled for later this year, will go a long way towards that. I would like to sell The Year of Knots as an art piece. I will make two editions and sell one and see what happens.



See more of Windy’s work, and stay updated on her future work here.

The music in the video is Chopin's Third Ballade.

Played by George Ko, CEO of Giant Robot Media.