Why Tracy Sun Spends Time Dreaming Up Solutions For Impossible Problems

Success stories can seem just as fantastical as the fairy tales you (may have) loved growing up: Bold career woman finds herself in the right place at the right time, and poof, her fairy godmother mentor snaps her fingers, transforming our hero into an overnight success who brings home a 7-figure salary, jet-sets the world spreading her you-can-have-it-all gospel, all while looking awesome and Instagramming the whole thing. Umm...really? Why do we so rarely hear the other side of the story — the false starts, the waves of doubt, the failures, and the fuck-ups? Those late-night worries and, occasionally, breakthroughs that are so relatable to the rest of us?

Introducing Self-Made, Refinery29's newest column spotlighting the real stories that fueled success — the wins, the fails, and the curveballs —proving there's no one path to getting what you want.

What do you think the definition of self-made is, as it pertains to you?
To me, self-made means you’ve taken what the world has given you and turned it into something more. You can’t control the cards you were dealt, but you can control what you do with them.

What quality do you think you possess that’s made you a good candidate for self-making your destiny?
I’ve never been one to shy away from big challenges. I am invigorated by dreaming up solutions to seemingly impossible problems. This is why I love being an entrepreneur. I continue to leverage this passion in my current role at Poshmark where I focus on tackling our new growth initiatives.

You went to college to study pre-med and now you work in fashion. How did you end up making such a huge career shift?
I went from wanting to be a neurosurgeon to founding a technology company which is redefining the fashion industry. But the truth is, I’ve always been curious about human behavior. So in this way, my background in psychology provided me with a unique and relevant perspective to tackle consumer behavior in the fashion industry.

Tell us a lesson you keep trying to learn, that you hope to eventually master, business or otherwise?
I’m committed to not being governed by fear. I get scared just like anyone else, but I’m really working hard to learn to recognize the fear and then not let this emotion determine the outcome.

You got your MBA from Dartmouth. How did business school help you get where you are today?
I arrived at business school with a background in neuropsychology which made me very different from the rest of my class who had previously been bankers and consultants. One of the most valuable lessons I learned during my MBA is that the things that make me different are not necessarily a liability. That the diversity in thought that I bring to the table is valuable. This, in turn, helped turbocharge my comfort in situations when I am presenting new ideas or find myself in new situations.

Having said that, I don’t think you need an MBA to start a business. As an entrepreneur, you will never have all the knowledge you need to be successful. You will need to believe in yourself and then ask for help when you don’t know the answer.

What aspect of your path do you think has been the most motivational to other young women coming up through the ranks?
I didn’t have my career path perfectly figured out. I moved from science to fashion to tech, and who knows where I’ll end up in the future. I hope that this can be an inspiration to all those out there who are not sure what their calling is or want to find the courage to make a change.

I also hope that I can serve as a role model to women who want to be leaders in technology. Yes, the tech industry is dominated by men and there are not many female founders out there. But we are here. And we’re kicking some serious ass. So let’s take this opportunity to raise our hands and create change. We need more women in technology, and I want to encourage women to go after what they want.

My advice to existing or future female entrepreneurs out there: spend time and energy believing in yourself — that's the biggest step to getting other people to believe in you.

Before you co-found Poshmark, you had another startup that failed. How did you learn from that disappointment? Women are always told to fail like men, yet it’s still rare to hear women touting their failures.
What I learned is how to fail fast, learn from that failure, and get back up and try again. If I hadn’t tried again, Poshmark wouldn’t be here today. Own it, embrace it, and start all over again.

Silicon Valley is a notoriously hard place for women to be successful. What kind of support system to you rely on? Is there a girls’ club to counteract the boys’ club?I’ve put a lot of energy into building a strong support system comprised of both men and women — I don’t buy into the myth that there has to be two clubs. In my experience, most people in Silicon Valley will lend a hand when you need it, regardless of gender.

Being self-made means committing to self-care, too, to manage the process as well as all the unexpected pivots that come with it. How do you fuel and refresh yourself when shit really starts to get hard?
I have two go-to’s. The first is maintaining a strong support network. Create a trusted group of friends, family, and co-workers and lean on them. Create this network before you need them because once you really need them, you won’t have the bandwidth to invest in these relationships!

I also work hard to maintain a meditation practice. It helps me keep life in perspective. When I feel like shit has really hit the fan, I use meditation to take a step back, take a deep breath, and come back to the situation — things usually feel more dire in the moment than they really are.

What's your Self-Made Mantra, no matter where you might be in the process?
“This too shall pass.” This mantra reminds me not to get attached to feelings of success because those moment are fleeting. Similarly, I shouldn’t get too down when the lows arrive because those moments will pass too.

You announced in May that Poshmark sellers have earned over $1 billion. That’s incredible. How do you see the app continuing to grow?
Thanks, it truly feels like an amazing milestone! I’m so proud of how far our team has come and everything we’ve built. Our community of shoppers and sellers are everything to us, so we’ll always continue growing and innovating the platform for them. My dream is to build the Poshmark seller network into a global community and to continue scaling a platform that empowers men and women to build their own brands and fashion businesses. Seeing our community succeed is truly the best part of my job.

What are you generally doing at midnight?
Sleeping! I used to be a night owl, but I recently made a conscious effort to start going to bed early because I find that I’m most productive in the morning and like to get a jumpstart on the day. I recently moved closer to work, which cut down my commute time significantly. This allows me to get into the office early, put in a full day, and then have time to kick back in the evenings. Lifehack: get more sleep!