Anna Sian

Anna Sianimage c/o karmaloop


How did you get started at Staple – and how does your current role as Marketing Director reflect your personal aesthetic?

My career path was never a straight one. It’s been a circuitous journey, and a seemingly random one at that. But at each step I took risks, lived in the present moment and inched closer towards what I felt deep down was a better match for me. I received my Bachelor’s degree from Dartmouth in Psychological and Brain Sciences. Not because it was my dream to become a psychologist or psychotherapist or really work in brain sciences at all, but because I took one intro class and felt that human behavior, and why people do what they do, was most interesting thing to learn about. Plus, my parents were firmly against me becoming a studio art major, so it was somewhat of a compromise. So I graduated with this seemingly impractical degree and moved back to NYC, where I was born and raised.

What followed in my post-college years were multiple part-time internships and jobs that each spoke to a different part of my personality, which when combined, somehow represented a more holistic version of my Dream Job. Over the years, I edited an art magazine, interned at a human rights non-profit organization and in fashion, freelanced in photography and volunteered with a Filipina women’s organization, and worked as a hostess and runner at Japanese restaurants to supplement my income. Eventually I landed a higher paying job as a marketing assistant at an engineering firm, but I wasn’t passionate about the engineering industry and I felt my creativity being stunted in that corporate environment. And then — as both a blessing and a curse — I was laid off. Unemployed for months, I floated around NYC until my best friend asked me if I wanted to join her band, Ava Luna, which was started by another one of our classmates from high school. I sang backup harmonies at first and later also played the keys. As part of Ava Luna I was able to tour the US and Europe, play at SXSW, the US Open and other memorable shows, but it wasn’t all glamorous and it wasn’t enough to support me financially.

I suppose I was in the right place at the right time when jeffstaple of Staple Design needed a new assistant and I applied, interviewed, and was hired. For the first year I was still playing in the band and begging jeff for more and more time off to tour; eventually I was getting burnt out playing late night shows and coming to work in the morning. I had to choose between the band or the job, and Staple felt like the right choice. A year later, the clothing brand started taking off and there was greater need for marketing, at which point I was promoted. It seemed like everything that I had done in my fledgling career leading up to that point started to make more sense for the marketing work I would begin to do at Staple. Marketing at Staple requires me to use what I’ve learned from the worlds of fashion, psychology, photography, publishing, the music industry and NGOs all rolled into one.

Cultural trends constantly change. What do you do to stay relevant, connected, and ahead of the curve?

Cultural trends do change, like everything else. That’s why I don’t necessarily pay attention to trends. I think what keeps me and my work relevant to others is that I try to really listen to the things that truly interest me – if I myself am not inspired, then I can’t expect others to give a shit. What that means is constantly finding ways to travel outside New York or visit new parts of the city, reading, trying different food, supporting new artists, meeting new people and making unlikely friendships.

How do you keep track of your personal and business goals – and stay creative at the same time (even when you’re exhausted)?

Luckily my personal and business goals require creativity.

How important are mentors? Who is your mentor?

Having a mentor is necessary. My main mentor is my mother, who worked her butt off to get from the Philippines to NYC, started her own business and non-profit organization, all while constantly learning and trying to be a better person with each day.

What is your advice for women entering creative fields or starting their own business?

I haven’t yet started my own business, so I can’t offer any legitimate advice for that, but my advice to any woman entering creative fields is to take risks and say yes to exciting (albeit frightening) opportunities. The future will work itself out somehow, so be fluid – the only thing constant is change.


  • Place that inspires me the most… Crazy Legs Skate Club in Bed Stuy, Brooklyn… But honestly I’m most inspired every time I travel, and inspired again every time I come home to NYC.
  • I feel most powerful when… I am with my friends and family.
  • I love what I do because… My job allows me to be myself.
  • Define your idea of success… There’s little I can say here without sounding trite. But success to me is being able to do what you love while helping others.
  • Best advice I have ever received… Breathe.

Follow Anna on Instagram: @Annamal!

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