MasterClass with Dr. Charlie

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Abstract

This MasterClass lesson explores the inspiring story of Dr. Charlie, a physician and entrepreneur who overcame personal setbacks to create an entire new industry: the freestanding emergency room (ER). Through this lesson, students will learn critical strategies such as turning challenges into opportunities, maintaining financial discipline, and leveraging innovative ideas to solve real-world problems. This lesson highlights principles of accountability, action, and authenticity, empowering individuals to apply these insights toward personal and professional growth.

Part 1: Early Vision — Becoming the Best Caddy

Dr. Charlie’s journey is a testament to resilience, adaptability, and visionary thinking. Born into a blue-collar family in the suburbs of Boston, he grew up surrounded by a culture of hard work and determination. The concept of hardship never fazed Charlie—instead, he focused on creating opportunities and worked tirelessly to achieve them.

At just twelve years old, Charlie took on his first job as a caddy at a local golf course, a seemingly modest role that quietly laid the foundation for his future success. Charlie didn't take the job to earn pocket money. He wanted to build a better life, and he recognized the job as an early opportunity that could put him on the path to more opportunities.

Think of this like planting seeds in a garden: at the time, they may look insignificant, but with time, care, and persistence, they bloom into fruit-bearing trees. Charlie began planting those seeds as an early hustle.

We should all learn from this lesson in personal development. By investing time and energy today, we put ourselves in the pathway for more options in the future. Regardless of where we are, we should think about the relationship between today's decisions and tomorrow's opportunities. Through his role as a caddie, Charlie learned to cultivate discipline, responsibility, and an understanding of human interaction. Those lessons proved invaluable to the career he built.

While many of his peers spent their summers seeking carefree fun, Charlie was hard at work at the Winchester Country Club, carrying golf bags under the sweltering sun. The physical demands of the job didn't bother him, as he routinely carried the heavy golf bags over his shoulder for two 18-hole rounds on each shift. Through those efforts, he mastered the art of anticipating the needs of those he served and embraced the values of perseverance and dedication. Observing the golfers, he absorbed invaluable lessons in strategy, decision-making, and patience—skills that would shape his approach to life and career.

Part 2: Strategy From the Sidelines

Through conversations with club leaders, Charlie noticed a common thread among those who had achieved success: they owned businesses, managed assets, or excelled in distinguished careers as professionals or physicians. Inspired by their accomplishments, he set his sights on a similar path, recognizing that higher education would be essential. Yet, the cost of college seemed insurmountable for his family.

Then he discovered a scholarship program for exceptional caddies. Determined to seize the opportunity, Charlie set a goal to become the best caddie at the club. With relentless dedication, he honed his skills, earning trust and demonstrating unwavering reliability. His commitment to excellence opened doors he never imagined possible.

That hard work paid off when the Country Club recognized his efforts and nominated him for a highly competitive, full-ride scholarship—granted to outstanding caddies who excel academically and embody exemplary character.

Charlie appreciated the reward that came from his dedication and perseverance. The club leaders saw his immense potential and awarded him the prestigious scholarship, a life-changing moment that marked the beginning of an extraordinary journey. His story serves as a powerful reminder that even the humblest roles, when approached with purpose and excellence, can lead to remarkable opportunities.

Part 3: Pragmatism in Action — The Bartender Scholar

During his undergraduate studies, Charlie learned an essential lesson about pragmatism and adaptability. Aware that he needed to support himself financially, he recognized an opportunity that went beyond just earning money. In Massachusetts, 18-year-olds could legally enter bars and drink, making bars a prime space for social interaction and relationship-building. However, without money, Charlie knew his time in such social settings would be limited. Becoming a bartender presented the perfect solution—it allowed him to earn an income, gain valuable skills, and connect with a diverse range of people.

Charlie’s story offers a compelling example of pragmatism in action. Pragmatism, a philosophy rooted in practicality and results, encourages finding effective, real-world solutions rather than being constrained by ideals or theory. By choosing bartending to meet both his financial and social needs, Charlie demonstrated this mindset. He creatively leveraged the resources and opportunities available to him, charting a practical path toward his goals. His story reminds us that success is often about taking thoughtful, strategic steps to address immediate challenges, rather than chasing lofty ambitions.

Through bartending, Charlie gained much more than learning how to mix drinks. The role taught him the importance of connecting with people from all walks of life, listening to their stories, and understanding different perspectives. These interactions sharpened his communication skills and deepened his appreciation for hard work, adaptability, and resilience.

Despite working full-time, Charlie excelled academically, achieving outstanding grades in college. He attended a liberal arts institution, majoring in chemistry—a unique combination that provided him with a strong foundation in both scientific theory and the philosophical and psychological disciplines. This blend of academic knowledge and real-world experience gained behind the bar enriched his understanding of people and the human condition.

Part 4: From Liberal Arts to Lifelong Learning

Charlie’s decision to pursue medical school was influenced by the depth and diversity of his education. During his admissions interview, he was asked what made him a standout candidate. Charlie explained that working as a bartender while studying liberal arts had given him a well-rounded education. He emphasized the importance of a Socratic mindset, and embracing the humility of recognizing how much there is to learn.

"By acknowledging how much I don’t know," Charlie shared, "I’ve committed myself to being a lifelong learner." It was this combination of intellectual curiosity, practical experience, and adaptability that ultimately convinced the medical school to accept him.

Medical school tuition was steep, but Charlie’s pragmatic approach helped him chart a clear path forward. Instead of taking on overwhelming student loan debt, he pursued a military scholarship. Leveraging his exceptional resume and a connection with his uncle, a high-ranking military officer, Charlie secured funding that covered his tuition, books, and living expenses. In exchange, he committed to one year of military service for each year of medical school—a calculated decision that paved the way for his future without financial burden.

Part 5: Growth Through Service

After graduating from medical school, Charlie was called to serve in the military. He was stationed at a base in Texas, where he began treating service members and honing his medical skills. Following his deployment, he advanced to an internship, gaining an additional year of hands-on training. During this time, he immersed himself in various disciplines, including orthopedics, emergency medicine, cardiology, and other specialties. His dedication and talent did not go unnoticed. Recognized by his superiors, he earned a coveted residency in orthopedic surgery—one of the most competitive and challenging fields in medicine.

Despite a significant accomplishment, Charlie shares how he lost the chance to pursue a career as an orthopedic surgeon. A verbal confrontation with a general led to unforeseen consequences. Using his influence, the general blocked Charlie's hard-earned residency. Instead of advancing in orthopedics, Charlie was reassigned to a base in Alaska, where he was tasked with leading a clinic while completing his responsibility and obligation to military service.

While stationed in Alaska, news came that our country had entered into war in the Middle East. As a captain, Charlie had the authority to decide who among his team would be sent to the battlefield. "I lead from the front," he explained. "I knew I had more experience than the other doctors under my command. Plus, I was single, while they were married with families. Although I could have sent them, I chose to assign myself to the mission overseas, fully aware I might not return alive."

After months on the battlefield, Charlie returned to Alaska with a renewed sense of purpose. Determined to complete his residency as an emergency room physician, he also decided to confront a lingering issue. He reached out to the general with whom he had previously clashed, offering a sincere apology for his past behavior. Charlie acknowledged his mistake, admitted the general had been right, and humbly requested permission to return to the Texas base. His goal was to fulfill his final year of military service while mentoring other physicians to excel in emergency medicine. The general, moved by Charlie's humility and commitment, accepted the apology and granted his request without hesitation.

Charlie’s story reminds us that success after a crisis begins with self-reflection and humility. When he faced the consequences of his past mistakes, he could have stayed bitter or given up entirely. Instead, he chose to take responsibility for his actions, acknowledging where he had gone wrong. This is the first step toward moving forward—taking an honest look at ourselves and owning our decisions, no matter how difficult that may be. It’s through this self-awareness that we are able to identify what needs to change and set a course for improvement.

Equally important is Charlie’s courage to take the next step—reaching out for a second chance. This wasn’t an easy decision. He had to risk rejection and revisit a relationship that hadn’t ended well, but he was determined to make things right and find a way forward. When we are confronted with challenges, we must adopt the same mindset. It takes persistence to rebuild trust, ask for help, or open a new door, but each step we take strengthens our resolve. Remember, setbacks don’t have to define us. What defines us is how we respond—by getting back up, learning from our experiences, and taking deliberate steps toward the success we desire.

Part 6: From ER Doctor to Entrepreneur

After completing his military service, Charlie embarked on a journey to build his career. As an emergency room physician, he often felt tied to the hospital, where private business groups typically managed operations. These groups contracted with the hospital to provide services, charging fees to cover expenses, paying doctors their salaries, and splitting profits with the hospital based on prearranged agreements.

For the first decade of his private practice, this system worked well. However, over time, the business group began cutting physician pay, leaving Dr. Charlie disillusioned. Frustrated by trading his time for diminishing wages, he reflected on a lesson from his youth, gleaned from conversations with golfers at the Winchester Country Club: true progress comes from owning a business. Inspired by this principle, Dr. Charlie decided to chart a new course and become an entrepreneur.

Charlie envisioned a solution modeled after freestanding surgery centers. Recognizing an opportunity, he began laying the groundwork for what would become the freestanding ER industry. While working for the business group, Charlie's focus was solely on delivering his services. Transitioning to life as a businessman, however, meant taking on far greater risks and responsibilities. Determined to move forward, he devised a plan and presented it to the bank.

His idea addressed a common frustration: the long hours patients often spent waiting in emergency rooms. Traditional emergency rooms prioritize ambulance cases, meaning someone with a broken arm or sprain might endure lengthy delays. Charlie envisioned a solution—creating a stand-alone emergency room designed to save patients time while offering a superior experience.

He imagined his facility as a haven for walk-in patients and referrals from other doctors, distinct from trauma centers overwhelmed by ambulance arrivals. To turn this vision into reality, Charlie needed capital. Committed to his goal, he put his own home on the line and worked closely with a local banker who believed in his clarity and passion. With a business plan in hand and conviction in his voice, he secured a $350,000 Small Business Administration (SBA) loan.

With these funds, Charlie leased a space in a medical office building and equipped it with approximately $100,000 worth of essential medical tools. From X-ray machines to lab equipment, everything was chosen with patient care and efficiency in mind. He approached the launch with the same precision and intentionality that had carried him through medical school and military service.

On opening day, the team was small but mighty: Charlie served as the physician, his wife ran the front desk, and one nurse assisted with lab tests and patient intake. The operation was lean, but the foundation was solid.

Part 7: Execution Over Ideation

Charlie’s ability to execute distinguished him from passive dreamers. As he often explained, “Ideas alone hold no value without action.” To craft a welcoming, high-quality experience, he drew inspiration from high-end hospitality. “I wanted patients to feel like they were walking into a Del Frisco’s Steakhouse,” he said, not just another sterile clinic. From interior design to staff uniforms, every detail reinforced a premium standard of care.

Marketing was just as intentional. Charlie personally visited local doctors and urged them to refer non-critical cases to his clinic. He was a known figure in the community—respected, experienced, and trusted. That reputation, combined with his hustle, helped bring in the first wave of patients.

Billing was a challenge he embraced. Rather than outsourcing, Charlie took billing and coding classes to ensure every claim was filed accurately. He billed insurance companies roughly half of what hospitals charged, making his clinic a cost-effective solution while still being profitable. He understood that money didn’t come immediately—insurance payouts could take months. That meant he needed to manage cash flow and reserves meticulously, always planning several steps ahead.

Charlie recommends entrepreneurs have at least a year’s worth of capital when starting. He had only six months, but he also had a contingency plan: if things didn’t work, he could return to ER shifts temporarily. Fortunately, the clinic gained traction. The first year brought in about half a million dollars in revenue.

Soon, Charlie opened a second clinic—this time with a partner who offered startup capital in exchange for a share of the profits. The partnership worked at first. The second clinic generated $6.5 million in its first year, fueled by optimized billing and operational experience from the first location.

Part 8: Challenges, Integrity, and New Purpose

However, success brought new challenges. Charlie’s partner refused to honor their agreement to continue building and sharing profits. A dispute followed. Charlie had no patents or legal protections for his freestanding ER model. His partner betrayed him, giving him a painful reminder that business relationships need clear contracts and strong boundaries. Rather than dwell on the setbacks, Charlie leaned into his resilience. He took what he learned and focused on recalibrating.

Charlie’s story is a modern blueprint for transformation. In a subsequent MasterClass lesson, we’ll reveal more about the parade of horribles that followed for Charlie after his partner’s betrayal–it’s the reason he now volunteers with our nonprofit.

Vocabulary Development

1. Hardship - Severe difficulty or adversity.
2. Accountability - Responsibility for one’s actions or decisions.
3. Adapt - To adjust or modify for new purposes or conditions.
4. Action - Striving toward a goal through proactive measures.
5. Pristine - Fresh, clean, and free from error or contamination.
6. Authenticity - The quality of being genuine and true to one’s values.
7. Optimize - To make the most effective or functional use of something.
8. Sustainability - The ability to maintain or support over the long term.
9. Execution - The act of carrying out plans or decisions.
10. Visionary - Someone who imagines future possibilities with creativity and innovation.

Straight-A Guide Lessons Recap

1. Values - Charlie defined success through innovation and patient-centered care.
2. Goals - His SMART financial and operational goals turned vision into reality.
3. Attitude - A growth-oriented mindset fueled his entrepreneurial journey.
4. Aspiration - He aspired to redefine patient care through efficiency.
5. Action - Taking decisive steps, he overcame financial hurdles to scale his business.
6. Accountability - Pristine documentation reinforced trust and progress.
7. Awareness - Charlie identified market inefficiencies and provided solutions.
8. Authenticity - Guided by honesty, he built valuable relationships.
9. Achievement - Milestones such as opening additional clinics reflect his tangible success.
10. Appreciation - Charlie’s mentorship exemplifies his gratitude and desire to give back.

Self-Directed Reflection Questions

1. What specific steps can you take to hold yourself accountable for your personal transformation?
2. How can adapting to challenges strengthen your ability to achieve your goals?
3. Why is maintaining pristine documentation and financial discipline crucial in both personal and professional contexts?
4. What actions have you taken recently to transform setbacks into opportunities for improvement?
5. How do authenticity and honesty build trust in relationships, both personally and professionally?
6. Why is taking risks important in the pursuit of long-term success?
7. How can observing successful individuals in your community inspire personal growth?
8. Why is continuous self-education essential for sustained development?
9. What lessons can you draw from Charlie’s entrepreneurial process to apply to your current goals?
10. How can you use the principles of resilience and adaptability in your own life?

Sample Response

While incarcerated, it’s important for each person to work on personal development, just as Charlie did. I provided the self-directed questions above as a prompt. Consider each question, and work to come up with an answer. There are no right or wrong answers. But prepare yourself to defend them. You should build this body of work to show the future stakeholders whom you will meet have you’ve continuously worked on personal development, even while in the face of adversity. As an example, I’ll write a sample response. I’ll write from the perspective as if I were just starting my term in prison, sharing the lessons I would have learned from working through this MasterClass on Doctor Charlie.

Question: What specific steps can you take to hold yourself accountable for your personal transformation?

Response (from the perspective of someone newly incarcerated):

When I walked into prison, I knew I had two choices: I could waste the time, or I could use it to prepare for a better future. I didn’t know how long the road would be, but I understood that no one else could transform my life for me—I had to own that responsibility.

After watching Dr. Charlie’s MasterClass, and working through the lesson, I saw a reflection of the mindset I want to build. He didn’t wait for ideal circumstances—he made the most of every opportunity, from caddying at twelve to learning medical billing on his own. That lesson hit me hard. If he could do it with limited resources, so could I.

So here are the specific steps I’m committing to for my own transformation:

1. Daily Journaling: Each day, I’m writing about how I spent my time—what I read, what I learned, how I responded to challenges. This will help me stay accountable and create a record of growth.
   
   
2. Setting SMART Goals: Like Charlie, I’m breaking down long-term goals into short-term, measurable steps. Right now, my first goal is to earn my college degree. I’ve set a deadline and a weekly study schedule.
   
   
3. Seeking Mentors: I’m identifying positive role models in here—guys who are using their time constructively—and I’m learning from them. I’ve also reached out to programs like this one to stay connected to outside mentors.
   
   
4. Documenting Progress: I’m building a personal portfolio—writing essays, completing program certificates, and saving letters of support. Like Charlie’s attention to documentation in business, I want my efforts to speak for themselves one day.
   
   
5. Self-Reflection: Once a week, I reread my journal and evaluate my progress. Where did I fall short? What can I do better next week?
   
   

I may be locked in now, but I’m building the foundation for the man I want to become. That’s my way of taking control. That’s how I hold myself accountable. And one day, I’ll be able to look a judge, an employer, or a parole board in the eye and say, “This is what I’ve done with my time. This is who I am now.”

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Supplemental Book Recommendation for Independent Study

Title: Grit: The Power of Passion and Perseverance
Author: Angela Duckworth

Summary of the Book:

Grit explores what makes people successful—not talent alone, but the combination of passion and sustained persistence over time. Angela Duckworth, a psychologist and former teacher, shares stories from West Point cadets, spelling bee champions, and business leaders to highlight how grit—not genius—is the key predictor of achievement. Duckworth also dives into scientific research and her own life experiences to offer insights into how grit can be cultivated in ourselves and others.

Why This Book Relates to Dr. Charlie’s Lesson:

Dr. Charlie’s journey is a living example of grit in action. From caddying at twelve years old, to bartending through college, to overcoming military setbacks, and later risking everything to build a new industry—his story reflects the very qualities Angela Duckworth defines as grit: sustained passion, deliberate practice, resilience in the face of failure, and the refusal to quit.

This book deepens the core takeaway of Charlie’s lesson: it’s not brilliance or privilege that drives long-term success, but perseverance and purpose. Learners will benefit from studying how grit is developed, and how they can apply that mindset to transform their own lives—whether they’re navigating hardship, reinventing themselves, or building something new from the ground up.

Title: Can’t Hurt Me: Master Your Mind and Defy the Odds
Author: David Goggins

Summary of the Book:

Can’t Hurt Me is a gritty, unfiltered memoir by David Goggins—an elite Navy SEAL and ultra-endurance athlete—who overcame extreme childhood abuse, poverty, racism, and self-doubt. Through brutal self-discipline, mental toughness, and relentless accountability, Goggins transformed himself from a 300-pound exterminator into one of the toughest men alive. The book shares his story while offering “challenge exercises” for readers to push past their own limits.

Why This Book Relates to Dr. Charlie’s Lesson:

Like Dr. Charlie, Goggins didn’t come from privilege. He forged a new path through intentional suffering, self-reflection, and extreme personal ownership. Both men faced institutional rejection—Charlie lost his orthopedic residency, Goggins was turned away by military recruiters. Both responded by looking inward and fighting forward.

Goggins’s message—that we’re all capable of much more than we think—reinforces Charlie’s example of transforming pain into purpose. Readers who engage with Can’t Hurt Me will be inspired to reframe adversity as training, and to adopt the mental armor necessary to pursue long-term goals through discomfort, discipline, and action.

Of course. Here is a third book recommendation that aligns deeply with the themes in Dr. Charlie O’Hearn’s story:

Title: The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph
Author: Ryan Holiday

Summary of the Book:

Inspired by the ancient philosophy of Stoicism, The Obstacle Is the Way teaches that adversity isn't something to avoid—it’s something to embrace. Ryan Holiday draws from the lives of historical figures like Marcus Aurelius, Theodore Roosevelt, and Amelia Earhart to show how they used obstacles as fuel for growth. The book lays out a practical framework for turning hardship into strength using three disciplines: Perception, Action, and Will.

Why This Book Relates to Dr. Charlie’s Lesson:

Dr. Charlie’s path exemplifies the central thesis of this book. Whether it was being reassigned to Alaska, losing a coveted residency, or navigating broken business partnerships, Charlie continuously faced obstacles that could have derailed his future. Instead, he reframed each setback as a stepping stone—much like Holiday teaches.

The Obstacle Is the Way helps readers shift their mindset: from frustration to focus, from helplessness to resolve. It reinforces one of Charlie’s greatest life skills—turning challenges into catalysts for reinvention and impact. This book will help learners internalize that power, reminding them that the way forward is often through, not around, adversity.

Challenge

Develop a personal profile on Prison Professors Talent. Use this space to document how self-directed learning has prepared you for success and to show the extraordinary actions taken to grow while overcoming adversity. Highlight your accountability, authenticity, and action for stakeholders who support your path to a law-abiding, contributing life.

Don’t be a complainer. Learn how to master your environment and put yourself into position to seize new opportunities. It’s never too early, and never too late to get started.

Challenge

Develop a personal profile on Prison Professors Talent. Use this space to document how self-directed learning has prepared you for success and to show the extraordinary actions taken to grow while overcoming adversity. Highlight your accountability, authenticity, and action for stakeholders who support your path to a law-abiding, contributing life.

Don’t be a complainer. Learn how to master your environment and put yourself into position to seize new opportunities. It’s never too early, and never too late to get started.

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