Inside the OB-GYN mind: Career moves that shaped doctors’ paths

There’s no single blueprint for the obstetrician and gynecologist (OB-GYN) profession — and rarely is it a straight line from medical school to an “established” career. Rather, for most clinicians, the path is shaped by a patchwork of ambition, adaptation, and trade-offs: lifelong values, detours that don’t feel ideal, logistical compromises when unforeseen life events happen, and encouragement from peers along the way. 

It may not be an easy or simple task to build a sustainable career as an OB-GYN. But Dr. Jennifer Boyle, OB-GYN at Massachusetts General Hospital, and Dr. Allison K. Rodgers, reproductive endocrinologist and OB-GYN at the Fertility Centers of Illinois, offer examples of two distinct trajectories: one rooted in generalist care and academic medicine, the other in subspecialty training. 

Here, the pair — who both sit on Flo’s expert board — discuss what got them where they are today and share advice for younger clinicians looking to carve their own path.

Discovering a calling in female health

Dr. Jennifer Boyle has been a general OB-GYN at Massachusetts General Hospital since 2012, where she splits her time between clinical work and teaching medical students. She also spends one day a week working at a community health center. She completed her residency at the University of Colorado after earning her medical degree from Rush University Medical College and is also a member of the American Board of Obstetrics & Gynecology.

But before any of this, Dr. Boyle studied an undergraduate degree in Spanish at the University of Notre Dame in Paris. It was here that she found herself most engaged by classes that examined feminism, humanity, and culture — and where her draw toward female health began.

“Women can be held back by health and medical concerns that affect women specifically,” she elaborates. “I wanted to go into medicine with the primary goal of advancing female health and, through this, women’s lives and place in society generally. Plus, when women are healthier, their families and children are also healthier — and our society as a whole is healthier.”

Dr. Allison K. Rodgers, meanwhile, has been a reproductive endocrinologist at the Fertility Centers of Illinois, US, since 2014. After getting her medical degree at the University of Michigan Medical School, Dr. Rodgers completed her residency in obstetrics and gynecology at MetroHealth and Cleveland Clinic before pursuing a fellowship in reproductive endocrinology and infertility at the University of Texas Health Science Center. She is also a popular creator on Instagram and TikTok, with 1.4 million combined followers.

“I just loved learning about reproductive health,” she says, reflecting on her time at medical school. “Being a parent is the most important thing in most people’s lives, and helping people grow their family and become parents seemed like the best job in the world.” That realization crystallized her decision to pursue OB-GYN work — and eventually reproductive endocrinology.

Choosing a path within obstetrics and gynecology

It’s no secret that obstetrics and gynecology is a particularly broad specialty, spanning general practice, high-risk care, and subspecialties such as fertility, oncology, and surgery. 

Dr. Boyle, for one, always knew she wanted to remain a generalist. Rather than subspecializing, she was drawn to the diversity of caring for patients with a variety of needs — and to working with medically underserved communities, particularly Spanish-speaking patients. “I liked the idea of working in a learning environment, where I could continue learning new things and be exposed to new ideas and research,” she says. And teaching medical students and residents felt like a natural extension of her work. 

Peers and mentors influenced Dr. Boyle heavily along the way. Those who inspired her most weren’t defined by grand titles or accomplishments but by how they showed up for patients daily. “I looked up to people who put caring for their patients first,” she says, “above research and even above teaching.”

For Dr. Rodgers, the decision to subspecialize in endocrinology emerged from her love of problem-solving. “I love solving puzzles,” she explains — from jigsaws and word puzzles to the intellectual challenge of identifying what’s wrong and how to fix it. Infertility medicine, with its diagnostic complexity and emotional stakes, felt like a perfect, and deeply meaningful, fit for her.

Residency, however, tested that conviction. Working more than 80 hours a week in emotionally and physically draining conditions, Dr. Rodgers found herself questioning whether she could see her fellowship through. But, similar to Dr. Boyle, it was a mentor who kept her going. 

“One of the fellows in my program insisted that I should pursue my dream, that it would be worth it,” says Dr. Rodgers. “She was so right.”

Detours, compromises, and unexpected growth

Career paths rarely unfold exactly as planned, and early misalignments can feel especially destabilizing in a medical career. But it’s helpful to know that one is never alone in this. 

“My career got off to a pretty twisty-turvy start,” admits Dr. Boyle, starting with what felt like limited guidance during residency. Afterward, she struggled to get herself set up in Boston, where she had no contacts, and after eventually interviewing for an academic generalist position that felt like her “dream job,” she didn’t get it. 

“I ended up taking a private practice job in a nearby suburb, which had not been my plan,” she says. “Part of what made me take the job, however, is that the head of the practice cared for his patients in a way that really resonated with and inspired me. I learned things from him that I still carry with me today.”

The following years brought more pivots: an unexpected move between private practices, an international detour into maternal–child HIV research in Botswana, and finally, a long-term dream role at the community health center.
Looking back, Dr. Boyle remembers feeling embarrassment and shame, assuming the instability reflected personal failure. Her advice to clinicians whose careers don’t start as planned? Make the best of it. Remember that “things don’t happen in straight lines,” and try not to worry about what it “looks like on paper.”

Dr. Rodgers’ compromises looked different but were no less significant. During training, she and her husband navigated years of uncertainty dictated by residency and fellowship matches — a system that often prioritizes institutional needs over personal lives. “He had to put his career as an attorney second so I could pursue my dreams,” she says. Once training ended, they chose stability, settling in Chicago, where they’ve now lived for nearly 15 years.

Facing the hardest parts of the work

Both physicians are candid about the intensity of OB-GYN work and the distinct kinds of difficulty it entails. 
Dr. Boyle describes two “buckets” of hardship. The first includes the grind: sleepless nights, endless documentation, patient expectations, and the many pressures of corporatized medicine. “The second bucket contains the things that are beyond hard — the things that feel like they can crush you,” she says. “These are the complications and the tragic outcomes — the times when you beat yourself up thinking you could have or should have done something different or better.”

To manage the first bucket, Flo’s guide to time-saving tips for overworked OB-GYNs can help. As for the second, “that’s the real challenge,” says Dr. Boyle. Writing, exercise, prayer, meditation, reading other physicians’ stories, and practicing gratitude all help get her through — but above all, she emphasizes the importance of accepting imperfection. 

“Trying to accept the contradictory dichotomy of needing to strive for perfection — and yet at the same time knowing that perfection is always beyond our control — is the key goal of surviving in medicine, and perhaps in life in general as a human,” she says. 

Dr. Rodgers echoes the emotional weight of obstetrics in particular. Medical training exposes clinicians to some of life’s deepest hardships, and there are days when doing everything right still isn’t enough. Still, “caring for people and helping them through the most difficult moments of their lives is a privilege,” she reminds us. “And to do it with compassion, knowledge, and strength makes it worth it.”

Working with Flo on the journey

Working with healthtech is just one of the newer opportunities for OB-GYNs among today’s shifting landscape. Both Dr. Boyle and Dr. Rodgers sit on Flo’s board of 100+ medical experts, helping shape and review the app’s content and features.

“Signing on with Flo really helped me find new energy in my career,” reflects Dr. Boyle. “Writing has always been something I wanted to do, and it helped me work on those skills — giving my life a spark of creativity that I really needed.”

It also helped Dr. Boyle fine-tune her patient education skills. “I’ve learned better ways to phrase and explain things to my patients. I’ve learned more about what interests them and what questions they have. In addition, I’ve learned so much about so many different topics by researching the amazing articles and questions that Flo generates.”

Taken together, these stories help illustrate that impactful OB-GYN careers aren’t defined by flawless planning or uninterrupted ascent. But whether through generalist care, subspecialty expertise, academic teaching, or healthtech, the common thread is intentionality — a willingness to reflect, adapt, and remain connected to the reasons the work mattered in the first place.

For clinicians still finding their way, that may be the most reassuring takeaway of all: Meaningful careers are built with time, often through paths that only make sense in hindsight.

Are you an early-career OB-GYN? Don’t miss these five lessons OB-GYNs wished they’d known earlier in their careers.