The Great Life of Being Self-Employed While Being Employed

This Week’s Real-Life Lesson

There’s something deeply gratifying about watching a colleague rediscover joy in medicine. Recently I met with a coaching client, let’s call him Dr. Happy, whose story beautifully captures the best of both worlds: the stability of employment and the autonomy of self-employment.

Dr. Happy is a real physician I’ve had the privilege of coaching through PEA-SimpliMD. For privacy, I’ve changed his name and omitted identifying details, but his experience is genuine, and it perfectly illustrates the power of structuring your professional life with intention.

He’s quietly built what I call the “Employment-Lite Life.” A rural family physician still delivering babies, managing a thriving clinic, and smiling about it, he told me, “I like being self-employed without feeling self-employed. I like the safety net of a great hospital relationship and the freedom to branch out.”

That single sentence captures the dream many of you share.

The Setting: A Doctor Who Designed His Own Framework

We met over Zoom one crisp fall evening. His community hospital, tucked away in a small Midwestern town, buzzes with the familiar rhythm of rural medicine: call schedules, clinic flow, and the upcoming implementation of Epic’s ambient AI documentation tool.

While most physicians feel trapped in that machinery, Dr. Happy has learned to work with it. His professional micro-corporation lets him operate in an “employment-lite” structure, receiving the security of a highly aligned contract with his hospital work that is translated into 1099 income through his own company for his professional services. He is also able to diversify his 1099 income through medical directorships, expert-witness legal work, and even creative woodworking projects.

It’s a hybrid model we teach inside the Physician Entrepreneur Academy (PEA-SimpliMD) is designed to give doctors the financial advantages of entrepreneurship while preserving the stability they value.

The Plan: Financial Freedom by Design

During our session, we refined his 10-year glide path, a plan to practice through age 62, then pivot to outpatient-only medicine with an option to retire by 67. His target? A $6 million net worth, built through thoughtful diversification and deliberate pacing.

His pillars are clear:

• Passive income through timberland and real-estate.

• Asynchronous expert-witness work for flexible, location-independent earnings.

• A micro-business foundation to capture the tax and benefit advantages that traditional employees miss.

He isn’t chasing an escape. He’s building alignment, medicine designed to serve his life, not the other way around.

The Joy of the “Employment-Lite” Model

Here’s why Dr. Happy’s approach works so well:

1. Hospital Collaboration + Independent Contracting: He enjoys self-employment W-2 perks like steady salary that he determines—and 1099 write offs like malpractice, CME—while channeling his side venture money as well through his 1099 entity.

2. Tax & Benefit Optimization: His micro-corp covers CME travel, retirement contributions, and deductible licensing expenses.

3. Lifestyle Flexibility: Asynchronous income streams let him visit kids scattered across the country without stress.

4. Purposeful Workload: One new OB patient a week keeps him clinically engaged without exhaustion.

5. Creative Expression: His woodworking studio produces joy and community connection more than profit.

It’s a life engineered for balance, the psychological safety of employment blended with the creative satisfaction of entrepreneurship.

The Bigger Picture: Your Best Life Is Built, Not Found

I often remind physicians that freedom is a function of structure. (do you remember that from biology??)

Dr. Happy didn’t torch the old system; he reshaped it. Through his micro-business, he became a doctor-owned enterprise within the institution, rather than an employee inside it.

This echoes my post “Say Yes to Self-Employment” where I argue that autonomy doesn’t require rebellion, it requires redesign. You can still collaborate with hospitals, leverage their infrastructure, and yet own your professional destiny.

If you’ve ever wrestled with the tension between safety and freedom, the “employment-lite” model may be your solution.

He didn’t reinvent medicine—he re-engineered his relationship with it.

The Wealth Accumulation Flywheel

If you’ve seen my Physician Wealth Accumulation Strategies framework, you’ll recognize the pattern: employment → self-employment → business ownership → freedom.

Dr. Happy now sits in the sweet spot, turning earned income into appreciating assets that compound his time as much as his money. His planned timberland investment, for example, will fuse passion with profit, offering tangible value and tax advantages all while fueling his love for wood working.

What You Can Learn from Dr. Happy

1. You Don’t Have to Quit to Be Free. Start by carving out a 1099 stream within your current setup.

2. Use a Micro-Corp as Your Freedom Vehicle. It’s more than a tax strategy, it’s your professional control center.

3. Design Your Career Around Your Life. Don’t wait for administrators to offer balance, create it yourself. (Download my free e-book “Design Your Career Around Your Life” for a step-by-step guide.)

4. Think in Decades, Act in Quarters. Big visions require small, consistent execution.

“Is This Deductible?”

Question: Can I deduct my IMLCC license fees for multi-state telemedicine work?

Answer: Yes. When you operate through a professional micro-corporation, IMLCC and state medical licensing fees qualify as ordinary and necessary business expenses, they directly support revenue generation and compliance.

The Surprising Insight

What struck Dr. Happy most wasn’t the money, it was the peace.

“I feel content,” he said. “I’m busy, but not too busy. I’m home for dinner most nights. I still get to deliver babies, and I actually enjoy it again.”

That’s the hidden ROI of entrepreneurship: calm confidence. When your structure aligns with your values, work starts to feel like calling again.

Join the Movement

“Freedom is the oxygen of the soul.” — Moshe Dayan

Thousands of clinicians are rewriting their careers through micro-business ownership. Ready to join them?

👉 Join the PEA Explorer Membership to access the community, courses, and coaching that help you design your own employment-lite life.

And download your free guide, “The Entrepreneur Physician’s Guide to Escaping Corporate Medicine” to get started today.

Final Thought

There’s a myth that independence requires quitting your job. It doesn’t. It requires owning your structure.

As I ended our call, Dr. Happy laughed and said, “I feel like I’ve cracked the code.”

He truly has. He serves patients with joy, supports his family, travels freely, and controls his professional destiny. Proof that the great life of being self-employed while being employed is absolutely possible.