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Learning how to be a leader through life’s challenges

Date: October 12th, 2022 in Faculty, JABSOM News, OB-GYN    Print or PDF

“My journey is one where…I feel like somebody is expecting to hear this very ambitious drive that got me from Point A to Point B to Point C. It’s not like that at all,” Dr. Holly Olson, prefaced her talk for this year’s Women in Medicine Speakers Forum.

Her talk, which chronicled her upbringing in Ohio to her journey of medicine in Hawai’i, was filled with many ups and downs. She shared her story “to let you know that challenges are the things that make us who we are and they help us define our priorities.”

The Women in Medicine Speakers Forum was part of JABSOM’s Diversity Matters 2022 series. It was also part of the American Medical Association’s Women in Medicine Month, which had the theme of “Leading with Purpose.”

For Olson, Associate Professor of Obstetrics and Gynecology at the John A. Burns School of Medicine (JABSOM), purpose is what served as her motivation to leave her native Ohio after high school, in light of the recession in the ‘70s.

Purpose is what brought her to West Point Academy to pursue a chemistry degree, where she battled imposter syndrome alongside her female classmates, constituting only 10% of the Corps of Cadets. Purpose is how she found the discipline and time management to join the school’s soccer team.

The idea of being a leader of a platoon, though, terrified her. The thought of having to lead a platoon in the army after graduation seemed overwhelming. That’s when she opted for medical school because she “could take tests, learn things, and medical school seemed like a good place to do that and use my chemistry degree.”

She was accepted to the Medical University of South Carolina. On graduation day from West Point, she got engaged to her husband, who she credited as a key part of shaping her leadership skills. In her second year of medical school, she was pregnant with her first child and decided to move in order to be with her husband. With the help of the dean of her school, she was able to transfer to Vanderbilt University School of Medicine after a leave of absence and with the permission of the Army, as the costs of her medical degree were funded by the Health Professions Scholarship Program (HPSP.)

Life threw Olson and her husband another curveball when her husband was deployed to the Middle East during Operation Desert Storm, leaving her to raise their newborn for the majority of her time left in medical school.

When her husband returned, they relocated to Hawaiʻi so she could begin her residency program as a Captain on active duty at Tripler Army Medical Center. During her second year of training, she found herself pregnant with her second child. She noted that raising her children helped shape her mentoring styles with her current trainees today.

Olson faced one of the biggest challenges in life in 2001, when her husband was killed in an Army helicopter training accident. A year later, her mentor and program director at Tripler, Dr. Michael Yancey, also passed away unexpectedly. In the months before his sudden passing, Yancey was training Olson, who was serving as the associate program director at the time, to take his place as director.

Suddenly, Olson found herself a single mom and in charge of running an entire residency program. She decided what was best for her, her family, and the program was to seek help and guidance from her department chair. The decision turned out to be a very important lesson in leadership for her.

“It was really this important lesson for me that, if you don’t ask for it, nobody is going to give it to you,” she said. “Nobody’s going to take something off your plate, if you don’t acknowledge…that you’re gonna drop that plate.”

It was also important for her, as a leader, to destigmatize the way people, namely her trainees, perceive getting mental health treatment or therapy. Olson spoke candidly about getting therapy as a way to cope with grief and the hurdles of being a single mom.

“It was so important for me to be able to tell my trainees that as a lieutenant colonel, I was getting therapy,” Olson explained. “Your career will not suffer if you get help.”

At the end of her talk, a Q&A forum opened up to allow attendees to ask Olson further questions. When asked what she hoped for the future of women in medicine, Olson replied with conviction that her hope was to continue to improve the working environment for women practicing medicine. To her, this included having access to family planning resources and making sure work schedules are flexible for those planning to or already have children.

“Creating an environment that is accepting of every woman as she is and her choices that she makes is so important,” Olson replied.

The choices, she explained, were the decision of whether or not to have children, and the timing of having and raising children while working. When asked about those next steps, Olson recalled a time she took a course on coaching, which she said she would use as her next steps.

“There is no way I alone can change the world, but if I coach other women to rise to their full potential, then together we can all change the world.”


The Women in Medicine Speakers Forum was part of the Diversity Matters 2022 series, an annual series presented by the Native Hawaiian Center of Excellence and JABSOM’s Office of Faculty Affairs. The series also included a presentation, “From Hawaiʻi to the White House: How I became a physician advocate” given by Kimberly S.G. Chang, MD, MPH, a Family physician and currently serves as Commissioner on the President’s Advisory on Asian Americans, Native Hawaiians, and Pacific Islanders; and a session titled “Freedom through Forgiveness” presented by Dr. Winona Lee, who served as co-chair of Diversity Matters alongside Lori Emory.

By Janell Agcaoili, JABSOM Communications

Watch the full video of Dr. Olson’s talk here:

Lori Emory, co-chair of Diversity Matters 2022, fixing Dr. Holly Olson’s lei for her presentation. Photo courtesy of Vina Cristobal.

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