Anna Fieler on finding the juiciest challenge

Anna Fieler is the Executive Vice President of Marketing at POPSUGAR Inc, where she oversees marketing for the company’s portfolio of brands including fashion shopping platform ShopStyle, lifestyle media property POPSUGAR, and monthly subscription business Must Have. Anna has a passion for building disruptive venture-backed businesses. She cut her teeth in Silicon Valley at eBay during its hyper-growth period, leading strategic marketing initiatives that contributed to the company’s growth from $430M to $7.5B in revenue. 

What did you want to be when you grew up?
An opera singer. Singing was my passion growing up and I took lots of voice lessons. In college I even took a semester off to prepare my audition tape and portfolio so I could apply  to transfer to a conservatory. Then I had a coach who said she would only recommend opera singing as a career if it was the only thing that could make me happy and that nothing else mattered as much. It felt like such a heavy question at 19-years old. I knew it made me happy but I wasn’t sure it was the only thing that could ever make me happy. She said that if I didn’t have the determination then I’d end up as a talented waitress in New York City. That gave me pause and made me think harder about not just what I loved but all the implications of such a choice.

Who would you invite to your dream dinner party?
Mark Twain: For his sense of humor, wit and sharp insight
Leonardo Da Vinci: I imagine him to be the ultimate Renaissance man
Mozart: Perhaps he could be inspired to compose and perform on the spot
Aristotle: Especially late into the night. He'd be the most interesting guest and the last to leave!
Maria Callas (American-born Greek Soprano): Just to be in her presence
Oprah: She would do an amazing job facilitating the conversation

What single book had the greatest impact on you?
Mindset by Stanford Professor, Carol S Dweck. The principle of the book is that your belief of who you are has profound impact on your life. In her research she has identified two mindsets: A Fixed Mindset or A Growth Mindset. A Fixed Mindset views attributes like intelligence as a fix attribute, whereas a Growth Mindset is much more about effort.

It's been really informative to how I think about my own career and how I think about certain situations where I catch myself facing things with a certain mindset. Especially how I view failure. For the Fixed Mindset, failure says something about me, whereas the Growth Mindset, failure is feedback for future effort. They are very different.

It's also had tremendous impact on my approach to being a parent. I've got two kids and I read a lot of parenting books but I feel Mindset been a very succinct framework for how I think about raising my children. I want them to view failure as feedback and not be afraid to fail. So the book as had tremendous impact on me, personally, professionally and  as a parent.

When do you go to bed and when do you get up?
On weekdays I go to bed at 10pm and wake up at 5am.

What is your favorite time of the working week?
Between 5:30am – 9:00am and 6:30pm – 9:00pm. I have a long commute and usually take a really early train. It's my uninterrupted time when I get to set my own agenda for the day. I always have my big cup of coffee, and I really treasure it. It's a gift of the routine.

Can you briefly explain your career path to date?
When I was at college my passion was opera and I was a Psychology Major. I was really interested in what motivates people to do things. When I went to college I didn't speak English very well and so Math was my strong suit. I had this weird combination of left-brain and right-brain. I was very confused about what I wanted to do with my eclectic combination of talents and interests. Unfortunately I didn't have many role models growing up so I wasn’t exposed to different career options.

One night when I was a senior in college, I walked by this lecture hall and I heard opera music pouring out of it. I walked in and it was a presentation by the legendary ad agency Leo Burnett. They were recruiting on campus. They were presenting a case study on a cheese brand that wanted to reinvent itself to be authentic Italian cheese. They demonstrated the process in researching the audience and understanding what the consumer wanted to unlock the insight. The Opera music in the background was the creative execution that convinced them that this cheese was now authentic Italian Cheese. Then they showed numbers and how it helped clients grow their business. I sat in the audience pretty dumbfounded. This seemed to be one career that combined arts, psychology and metrics. It felt like one career path that combined everything that I was either good at or passionate about. I left feeling extremely inspired and contacted the agency and subsequently did a week’s internship at the agency. That was my entree into the world of advertising.

After college I came to New York and worked on Madison Avenue at Ogilvy. I worked on Dove, which in the 90s was repositioning itself from a bar of soap to a beauty brand. It was a tremendous time to work on this iconic American brand at the precipice of transforming itself. After a few years in advertising, the internet was coming onto the scene and I was seeing the writing on the wall that advertising was going to become a much smaller piece of the puzzle. So I went to Business School.

I attended Harvard Business School and the dotcom boom happened. So after school I moved to Silicon Valley and worked at EBay for seven years during the time when EBay was very young and employed around 1000 people. By the time I left it was a big global business. That was my training ground into consumer technology.

From there I took on a few different "Head of Marketing" opportunities at different consumer companies. Most notably I was Head of Marketing and one of the early team at Tiny Prints. I helped build that brand from being a niche business to the leader in online customized stationery. The company was acquired by Shutterfly so I stayed and helped manage the transition and led marketing there. Then I went onto Stella & Dot and now I'm at POPSUGAR.

The common thread in my career is that I enjoy working on brands that speak to women and on products that really delight and service women. POPSUGAR is a brand that is very much about empowering women to be happy and healthy. I'm passionate about  helping  women lead a more fulfilling life.  

At POPSUGAR I head up marketing. The company is a unique intersection of content and commerce and has three distinct brands, so I have a unique marketing team for  the POPSUGAR media business, another for the SHOPSTYLE fashion search engine business and one focused on POPSUGAR MUSTHAVE subscription business.  

What is the biggest obstacle you’ve overcome in your career?
My personal obstacle was definitely motherhood. It stopped me in the tracks of my career. I didn't grow up with a biological mother so I had this idealized vision of motherhood. When I had my first child I was overwhelmed by the love I had for my baby and I thought being a good mom meant I could only focus on him, leaving me no room for an ambitious career.  I was in my early 30s and early in my career, and frankly my job wasn't always fulfilling. I wasn't calling all the shots or making all the decisions. Plus with the expense of high quality childcare it didn’t seem to make sense to continue working.

But I had also invested a lot in my career. I had attending business school, and I wanted both – career and motherhood. At that time I didn't have role models or clear vision and I interpreted balance in a very narrow sense of the word. I thought balance meant hours, how many hours I was working versus hours with my children. So I opted to take a part-time role. I remember a conversation with a manager back then, which went something like this: You can take this part-time role and spend more time with your kid or you can take this all-consuming promotion that won’t allow you time with your newborn. Of course I was going to choose my baby. I certainly felt like I would be a bad mother if I had chosen the other route, rather than thinking, could I have both?

So I gave up and was on the mommy track for a couple of years and even though my hours were balanced and I was getting paid a good salary, I didn't think I had picked the juiciest challenge I could be tackling. I felt like I'd opted out and I wasn't happy. Even though my hours were balanced, my energy was off-kilter because I wasn't being authentic and true to myself.

When I was on maternity leave with my second baby I reached a point where I needed to decide whether I would completely opt-out or put my foot on the gas because this pseudo-balance wasn't working for me. I worked with an executive coach to help me think through this issue and she encouraged me to think about balance more broadly. Funnily enough, it came back to that Fixed and Growth mindset. My Fixed Mindset was saying: You're either a good mother or you can have an ambitious career.

She encouraged me to adopt the Growth mindset of: could you have your cake and eat it too? So instead of opting out, when I came back from my maternity leave, I quit my cushy part-time job and leaned into a full-time role at a fast growing start up and completely went 180 degrees in the other direction.

I wouldn't say everyday is easy but in an odd way, I feel more balanced. It's taken a lot of soul searching, organization and figuring out what I can let go of. For instance, I like home cooked meals for my kids but store bought healthy meals are okay. My kids aren't always turned out neatly pressed in matching outfits and that's okay. We're still living in our starter home with the same furniture we got for our wedding gifts but that's just fine. I've really had to step back and ask myself, of these things, which one actually matters?

At the end of the day that's not what I'm going to derive personal satisfaction and balance from. What I've really had to learn is doing away with all the "shoulds".

What motivates you?
Creating an impact in somebody else's life: in the life of customers or the life of my team. It doesn't need to be grandiose. I don't need to be saving the world to create that impact but the fact that POPSUGAR's mission is to empower happiness, to me that is noble enough of a mission. It motivates me to work on a mission-driven business that seeks to create positive impact.

Personally, from the whole experience of seeking "balance", what motivates me is to be ‘in flow’ as much as I can. I really work on being present and trying to do things that really matter.

What advice would you give to someone at the start of his or her career?
Always find the juiciest challenge.

Don't be afraid to fail, take that as feedback.

Believe in effort and hard work.

What do you consider your greatest achievement?
I feel like I have a "balanced" life. I have a very happy life and I'm very satisfied with what I created.  When I was a child, I wouldn't have necessarily dreamed of this life I have today, so I feel like in some ways I created the life I wanted.

What do you believe has been the key to your success?
Tenacity and resilience.

What is the most important lesson life has taught you?
Life is what you make it and only you have the power to create your own path.

I was born in Taiwan and I never knew my biological mother. My father never went to college and didn't speak English. When I was 11-years old he decided to move the family, my stepmother and half-sisters, to the Dominican Republic.

I was in the sixth grade and put in a bilingual school. I didn't speak a word of English or Spanish and had to somehow navigate. Somehow by osmosis I learnt the languages and when I was 14-years old I met a girl in my class (who is still one of my best friends) and she introduced me to opera and all things Western. She also said she was going to boarding school in America. The concept fascinated me and I wanted to go too. Out of my own initiative I looked into all these boarding schools in the United States, made my father let me go and off I went.

After boarding school I stayed on to go to college and that's how I made it here. Then in college I was introduced to advertising... Fast-forward, three years into advertising and I was assigned to have a mentor through Advertising Women of New York. Upon meeting me in my very first meeting, my mentor suggested that I’d really enjoy business school and because she went to Harvard she recommended I give Harvard a try. And so I said, “why not!” A year later I was at Harvard Business School.

As a child from a broken home in Taiwan or even in the Dominican Republic when I didn't speak a word of English or Spanish, I could never imagine that I would one day live in California with a loving family of my own, complete with a house with white picket fence.  Although I didn’t know my destination or would even know a way of getting there, I seized opportunities as they presented themselves to guide me.

My greatest lesson has been to take charge of my own life and say "Circumstances be damned! I'm driving this agenda!”

What do you believe are the personality traits of great leaders?
Visionary: You want to paint the future state so that people will want to follow you.
Great Communicator: So you can communicate that vision.
Emotional Intelligence: ability to express and control your emotions, and also to understand and interpret emotions of others.

Do you believe there’s a secret to rising to the top?
Yes. I think it's being very comfortable with discomfort because rising to the top implies you're leaning in, you're pushing yourself and you're asking for things. That’s uncomfortable.

That discomfort can even initiate from the desire to want to be at the top. Every step of the way you've got to lean into the juiciest assignment that could stretch you and push you out of your comfort zone. You could be asking for a promotion, or an opportunity, or a raise... and that can be really uncomfortable. You may have to work with people who are challenging and difficult.

It's something I'm still working on. I think it's also something that women aren’t as good at than men. As women we're taught to make everybody happy, build consensus, make sure everybody feels good... rather than leaning into that discomfort.

Who do you turn to when the going gets tough?
My husband. We definitely have a 50/50 partnership. He's my best friend, my co-parent, my intellectual equal and my career advisor.

What's next?
I feel like POPSUGAR is at the precipice of becoming an iconic brand for American women. Making it bigger and making it global is extremely exciting. I’m driven to build it out as a multi-dimensionalized experience beyond digital.

For me personally, I feel like I’ve spent the last decade focusing a lot on my work, my family, and my immediate circle. Within the next year I’d like to get more involved in the community. I'm ready to expand my circle of influence.


As told to Caroline Hugall at POPSUGAR New York Office on Monday 27th April 2015.