Dr. Lena Cheng on Leaving Life as a Physician, Reinventing Through Healthcare Marketing, Co-Founding Best Friend Jack, and Finding Strength in Midlife Through Powerlifting and Dance
How do you pivot from a demanding medical career to founding a healthcare marketing agency, and then discover your true physical power in your fifties?
In this episode of No Boxes, Just Verses, I sit down with my friend Dr. Lena Cheng. Lena shares her incredible journey of honoring her internal compass, leaving clinical practice behind, and building a highly successful second career in digital health.
We discuss the importance of utilizing executive coaches, the reality of taking steps backward to leap forward, and how she is currently redefining midlife strength through barbell training and epic dance projects.
Lena Cheng, a physician turned healthcare marketer, has spent two decades leading brand strategy for healthcare companies. After medical training, she successfully pivoted, co-founding Best Friend Jack, a boutique marketing agency for health-tech companies, focusing on clarity and credibility. In her 50s, she embraced physical transformation through strength training, powerlifting, and dance, finding that movement taught her about presence, resilience, and courage. Her framework—Presence over Performance, Power through Resistance, Courage in Motion—reflects her belief that midlife reinvention is physical and a time of ignition, not decline.
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Key Takeaways:
The Immigrant Work Ethic: Lena opens up about growing up in the Bay Area, learning the value of hard work from her nurse-midwife mother, and realizing later that her early creative hobbies were actually clues to her true identity.
The Paris Epiphany: She explains how taking a year to study art and architecture in Paris during her undergrad showed her the expansiveness of the world and proved that other versions of a meaningful life were possible outside the rigid medical track.
The Painful Pivot: Lena gets incredibly vulnerable about the physical and mental toll of medical school, the difficult decision to leave clinical practice, and how she used executive coaches to rebuild her identity from scratch.
Building the Complete Marketer: She shares the humbling experience of starting over as a beginner in biotech, taking massive pay cuts, and eventually working her way up to head of marketing roles before co-founding her own agency, Best Friend Jack.
Courage Through Motion: We discuss her midlife physical transformation, how she fell in love with powerlifting, and why she believes you build courage by simply showing up and putting in the reps.
Lena’s story is a beautiful reminder that it is never too late to change your mind, change your career, or change your relationship with your own body. If you are feeling stuck in a box you outgrew years ago, this episode will give you the permission you need to step into your power.
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Theme Song: No Boxes Just Verses by Thane Kreiner (Suno)
Breaking the Doctor Box: 5 Lessons on Career Pivots and Midlife Reinvention with Dr. Lena Cheng
How do you walk away from a medical degree to start over as a beginner in marketing? And how do you reinvent yourself again as a powerlifter in your fifties?
For Dr. Lena Cheng, the answer is simple: you have to build courage through motion.
Lena is a physician turned healthcare marketer, entrepreneur, and co-founder of the boutique agency Best Friend Jack. On this week’s episode of No Boxes, Just Verses, Lena sat down with me to share the reality of massive identity shifts, the power of executive coaching, and why the most important transformations in midlife are entirely physical.
Here are five powerful lessons from her unboxed journey, told through the soundtrack of her life.
1. Your Earliest Joys Are Clues (Dreams - Fleetwood Mac)
Growing up in the Bay Area with immigrant parents, Lena was taught that hard work and the "grind" were the ultimate strategies for survival and success. Because she spent her childhood in hospitals with her nurse-midwife mother, becoming a doctor felt like the natural, unquestioned path.
But behind the scenes, Lena was lit up by drawing, painting, dancing, and learning French. For years, she minimized these passions as mere "hobbies." Looking back, she realizes those early joys were actually a truthful expression of herself—her body knew what she wanted before her head caught up.
2. Expose Yourself to Possibility (I Still Haven't Found What I'm Looking For - U2)
During her undergrad at Northwestern, Lena took a year to study abroad in Paris. It was a completely instinctive choice that changed everything.
Instead of heavy science courses, she took art history and architecture classes, meeting at the Louvre every week. That year abroad showed her how big the world really was and proved that there are many ways to live a meaningful life. It gave her the first physical feeling of expansive possibility outside of the traditional medical track.
3. Normalize Asking for Help (Stronger - Britney Spears)
Despite her growing intuition that medicine wasn't the right fit, Lena pushed through four years of medical school and three years of residency. The constant grind left her physically sick, depleted, and deeply unhappy.
Making the decision to leave clinical practice was one of the hardest choices of her life, and she didn't do it alone. During her first year of clinical practice, she hired an executive career coach. Lena’s story is a powerful reminder that we need to normalize getting a coach early in our careers, especially when navigating massive identity shifts and untangling our self-worth from our job titles.
4. Embrace the Discomfort of Being a Beginner (Don't Stop Me Now - Queen)
When Lena finally pivoted into the corporate biotech and marketing world, she had to start from scratch. She had no formal marketing experience, didn't know anything about drug development, and didn't even know how to use a 1-800 number for a conference call!
It was a shock to the system, but leaning into that discomfort built her resilience. She learned that the friction of starting over isn't a warning sign to stop; it is proof that you are building something new. That resilience ultimately gave her the confidence to co-found her own successful agency.
5. Reinvention is Physical (Body - Megan Thee Stallion)
Today, Lena is experiencing a new era of leadership by stepping into her physical power. In her fifties, she began barbell training, training for her first powerlifting meet, and returning to her childhood love of dance (including a fully choreographed and filmed Thriller recreation!).
Her song choice, Body by Megan Thee Stallion, represents the confidence of putting in the work, rep by rep. Lena’s ultimate lesson? You don't have to shrink one part of yourself to legitimize another. Midlife is a time for ignition, and true courage is found in motion.