When a Corporate Title Threatens Your Freedom: A Wake-Up Call

The Entrepreneur’s Life: When a Corporate Title Threatens Your Freedom: A Wake-Up Call 💼✨

This Week’s Real-Life Lesson

A few days ago, I opened an email that stopped me in my tracks. It was from a physician reader, a specialist who had built a thriving independent professional business after years of W-2 employment. He had just been offered something he used to dream about: a Vice President role at one of the hospitals where he has done contracting work.The kind of leadership title that, five years earlier, he would have chased relentlessly.

But now he was hesitating.

He wrote, anonymously:

“I was applying like crazy for this type of job 5 years ago with no luck because I wasn’t employed with the health system, nor was I working my way up through service line director, med staff, etc. Now finally I was being offered a VP role that could lead me to a CMO or CEO position in 7–10 years. But I would lose all the autonomy I have now. I needed the reminders from you — autonomy has been the real key to my happiness. Knowing this both informed and reinforced by decision to say “no" to something I had striven to attain.”

That message hit me hard because it captures the quiet crossroads every entrepreneurial physician faces. Do we climb through the traditional ladder, or protect the freedom we’ve built through independence? This physician’s “no” was not about the hospital, the C-suite, the title, the opportunity ,or the compensation. Rather, his “no” was more about saying “yes” to his identity and well-being as an independent physician entrepreneur.

The Trap of the Title

Early in my own career, I wanted titles too. I wanted to be the “Medical Director,” the “Chief of Staff,” maybe even the “CMO.” Each title promised influence and respect, but in truth, each one came with a higher dose of bureaucracy, meetings, and compromise. Honestly, as a high performing leader, it took me a while to figure out the corporate healthcare ecosystem was not the right sandbox for me to thrive in.

When you’re self-employed, whether through locums, telemedicine, employment lite, or the myriad of marketplace jobs available to 1099 independent contractors, your influence isn’t granted by a title. It’s earned daily through service, relationships, and ownership of your professional life.

That’s why I founded PEA-SimpliMD

• Autonomy is the foundation of professional happiness.

• Money follows mastery — and mastery thrives in freedom.

• Micro-business ownership gives doctors leverage, not just income.

This reader told me that my essay, Why the White Coat Investor Is Wrong About 1099 Income , helped him see the bigger picture again. That being a physician-owner isn’t only about deductions or tax strategy. It’s about agency: deciding how, when, and where you practice medicine.

Case Study: The VP Offer That Didn’t Happen

Let’s break this down as a case study in professional decision-making.

Scenario: A mid-career specialist working as a locums physician is offered a VP role.

Temptation: Prestige, leadership influence, pathway to C-suite.

Trade-off: Salary increase, but loss of flexibility, time, and entrepreneurial upside.

Financial reality: As a 1099 physician with a micro-corporation, his effective after-tax income and retirement acceleration already rival that VP salary, but without the meetings, politics, or relocation.

Emotional insight: The title “Vice President” would make him proud, but at the cost of the freedom he worked a decade to earn.

In the end, he declined the offer. And in doing so, he stepped even more fully into the identity of a Physician-Entrepreneur, not because of what he turned down, but because of what he chose to preserve.

The Deeper Lesson: Freedom Is the Real Flex

Every doctor who becomes self-employed eventually learns that freedom is worth more than income growth. When you can say “no” without fear, that’s the moment you’ve achieved true leverage.

You’ll never read about that kind of wealth in corporate HR handbooks. It doesn’t show up on a W-2. It shows up in how you spend your mornings, how you practice medicine, and whether you can walk away from a meeting that doesn’t align with your values.

If you haven’t yet made the leap to self-employment, start small. One side contract, one telehealth shift, one micro-corporation formation That’s how it begins.

Let’s talk about how you can get started by going here to set up a strategy session to get your professional independence started.

And if you already have, protect it fiercely. The world will constantly tempt you with titles, promotions, and prestige, but the greatest title you can hold is Owner.

Is This Deductible?

Last week, I met a few physician friends for dinner. Inevitably, our conversation circled around medicine, side gigs, and the wild growth of my new D2C cash pay acute infection treatment platform called ChatRx. Someone asked, “Tod, can we write this dinner off since were talking about business?”

My answer was: “If the meal had a clear business purpose, like discussing your entrepreneurial projects or professional collaborations, then yes, it’s deductible as a business meal under your micro-corporation.” When I got home, I turned my receipt into my corporate bookkeeper (my wife)✅.

Want to understand how to legally structure these deductions? Download my free guide:

👉 The Doctor’s Guide to Micro-Business Deductions

Join the Movement

“Entrepreneurship is the art of reclaiming your professional soul.” — Dr. Tod Stillson

Thousands of clinicians are leaving the W-2 hamster wheel and designing careers around freedom, creativity, and ownership.

Are you ready to join them?

➡️ Join the PEA Explorer Membership — it’s the perfect starting point to learn how to build your micro-business.

Want to go deeper and understand the long version of how I ended up here? Grab a free digital copy of my e-book Doctor Incorporated: Stop the Insanity of Traditional Employment, and start your journey toward autonomy today.