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Dreaming Big, Date Nights, and Redefining Failure with Dr. Rupa Wong

The Fabled blog brings together diverse women in medicine to inspire uplifting conversations about life as a medical practitioner. We want to create an empowered community through open discussions about traditionally off-limits topics such as self-care and non-linear career paths. We hope that by participating in these conversations, our readers will go on to live more fulfilling lives. Our new interview series shines a light on the power of personal style, mindfulness, and more.

Our Women in Medicine Q&A series continues with Dr. Rupa Wong, an ophthalmologist, entrepreneur, and managing partner of Honolulu Eye Clinic, where she specializes in pediatric ophthalmology and adult strabismus. Dr. Wong is the founder of Attending Lounge, an online community that empowers female pre-meds, medical students, and those in training. She is also the co-creator of Pinnacle, a community and conference dedicated to addressing the challenges faced by women physicians in private practice. Dr. Wong recently launched It’s Good To See You, a podcast about balance, time management, and being a boss. Read on to learn about her path towards medical school, her commitment to mentoring young women, and her penchant for sheath dresses and heels.

What inspired you to become a doctor? We want to hear it all: The good, the bad, and yes, even the ugly.

I come from a family of physicians. My mom and various aunts and uncles are all physicians. So, I grew up in the world of medicine, and it's always what I wanted to do. In fact, my parents tried to convince me to do something else, like law or engineering. My mom is a child psychiatrist, and I distinctly remember how hard it was for her to find someone to cover her private practice. My dad saw the stress and challenges that my mom faced as a physician, and they wanted me to choose an easier path.

What’s your #1 tip for young women entering a career in medicine today?

Don’t be afraid to fail. The word “failure” has such an ugly connotation, and we avoid it at all costs. I did the same: I remember poring over the course catalog when I was a sophomore at Duke, looking for the teachers who graded more easily or had good reviews. I was afraid I wouldn’t do well. As a result, I avoided challenging myself. But when you look at failure as a process of growth, it loses power over you. I have failed plenty in my journey as a physician, practice owner, and entrepreneur, but I have always grown from those experiences. 

Can you tell us if your Indian heritage influences your work, and if so how?

I can't say that my Indian heritage influences my work as a physician, but it has impacted my social media presence. When I started my account, I never anticipated the types of messages I would receive from South Asian women just starting out on their educational journey. Of course, there are a lot of South Asian American physicians in hospitals, but not as many in the media. I think sharing my personal story—the discrimination I've faced, the bullying when I was younger, and marrying someone who is of a different culture and faith—really resonated with my South Asian followers.


Dr. Rupa Wong


What inspired you to start Pinnacle?

The idea for Pinnacle came from something I've always thought about: Teaching women how to navigate the business side of medicine. I had no roadmap when I started my private practice with my husband 13 years ago. There was no one I could speak to about these topics, no mentor, no form of guidance. When I met my Pinnacle co-founders Dr. Natalie Crawford, Dr. Danielle Jones, and Dr. Pam Mehta, I knew they would help bring my idea to fruition. Pinnacle is now a space for women to dream big. To become more. And it's been amazing to watch.

Women supporting women is a big theme in your work. Can you talk about how this came to be a defining element for you?

I passionately believe in female mentorship, and pulling back the curtain of our daily lives so that others can learn from it. The same themes kept popping up in the questions that women would ask me. They spoke of feeling less than, and not good enough to succeed as a physician. I realized that younger women don’t just need the tools to ace their MCATs or their boards. They need the mindset strategies to be truly successful. That means learning how to overcome your limiting beliefs, how to deal with competitiveness, how to navigate work-life balance, and how to push past failures. These issues are what I address in my online membership site, Attending Lounge. So much can be accomplished when women support and collaborate with one another.

What do you love to do outside of your medical work?

I serve on the Board of Directors of three non-profit organizations, and I love to play tennis and enjoy Hawaii life with my three kids. I’m also absolutely addicted to my Peloton, and love lifting weights and working out at the gym.


Dr. Rupa Wong


What’s your favorite self-care ritual?

Date nights are a big deal for my husband and I, since we also work together. There’s a tendency to solely talk about the practice or the kids, so carving out date nights help us find time to connect. 

What do you wear to work, and how does it make you feel?

I’m usually a sheath dress and high heels kind of girl, even at work. But this past year had me living in scrubs and sneakers. To be honest, they were designer sneakers, but still! That's why I love Fabled so much. Fabled scrubs are like a suit: They look put together, but they’re still comfy. Plus, I can still wear my heels with them!


What does the idea of personal style mean to you, and how does your sense of style empower you?

I spent a month in Madrid when I was 16, living with a family friend. That period in my life really influenced my sense of fashion. I love the idea of putting your best self out there when you leave the house. I can still remember how dressed up the mom of my host family would get. Then, when she got home, she would change into her “comfy clothes.” Today, my style is very classic. I like pieces that will stand the test of time. My clothing empowers me. It makes me feel confident and strong. But it's not about impressing someone else. It's about my own self-acceptance.

Dr. Rupa Wong

Lightning round!

What song can you not stop listening to right now?

Harry Styles’ “Watermelon Sugar.” My kids love it. We put it on in the minivan and all sing super loud. 

What skill do you most want to master?

I'm starting a new podcast, so that's a skill I hope to master!

What TV show are you currently binging?

I just finished binging Shadow and Bone on Netflix.

Photographs courtesy of Dr. Wong.

We love talking with women in medicine who manifest self-care and self-expression. If you know someone who can teach us a thing or two, email us their details!

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