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Ep 226 Talking through leaving your job with Amanda Hill, JD

Episode Summary

In Episode 226 of the BOSS Business of Surgery Series, Dr. Amy Vertrees, general surgeon, certified coach, and founder of the series, is joined by healthcare attorney Amanda Hill to discuss one of the most important — and misunderstood — career decisions physicians face: how to strategically navigate job transitions.

This webinar-style episode focuses on empowerment, professional autonomy, and protecting physicians from costly mistakes when considering leaving a job. Rather than encouraging resignation, the conversation teaches physicians how to reclaim agency, understand their contracts, and make career decisions from strength rather than desperation.

Dr. Vertrees shares her personal journey from employed surgeon dissatisfaction to building a thriving private practice, while Amanda Hill provides legal insight gained from 23 years representing physicians across healthcare systems.

Together, they introduce a structured framework for evaluating career dissatisfaction, avoiding impulsive decisions, and preparing for either transforming a current job or exiting strategically.

Meet the Speakers

Dr. Amy Vertrees

  • General surgeon practicing at a nonprofit community hospital in Tennessee
  • U.S. Army veteran with 17 years of service and three combat deployments
  • Certified professional coach
  • Founder of the BOSS Business of Surgery Series (est. 2015)
  • Transitioned from employed practice to founding her own private surgical practice

Mission: Help physicians create freedom, autonomy, and professional fulfillment.

Amanda Hill, JD

  • Healthcare attorney based in Austin, Texas
  • 23+ years representing physicians
  • Experience with:
    • Veterans Affairs system
    • Large health systems
    • Federally Qualified Health Centers
  • Founder of Guard My Practice, focused on proactive physician protection

Key Insight: Most physicians seek legal help only after problems occur — when options are limited and expensive.

Key Topics Covered

1. The Changing Healthcare Landscape

The speakers discuss the dramatic cultural shift physicians have experienced:

  • Post-COVID decline in physician morale
  • Increased administrative pressure
  • Growing disrespect toward physicians
  • Approximately 10% of physicians leaving medicine, increasing workload for those remaining

Result: Many doctors feel trapped, exhausted, and unsure of their options.

2. The Truth About Jobs and Fulfillment

Dr. Vertrees introduces a powerful mindset framework:

Jobs provide:

  • Opportunities to learn
  • Circumstances to navigate
  • Choices to make

Jobs do NOT provide:

  • Happiness
  • Identity
  • Personal fulfillment

Relying on a job for emotional satisfaction gives away personal power to an institution that ultimately functions independently of any individual physician.

3. The Three-Step Job Dissatisfaction Analysis

Before making any career move, physicians should complete this process:

Step 1 — Define What You Want

  • Remove perceived limitations
  • Create a detailed, specific vision
  • Avoid vague dissatisfaction

Step 2 — Give Yourself Permission to Complain

  • Vent without judgment
  • Complaints reveal unmet desires
  • Clarity comes from honesty

Step 3 — Expand Perspective

  • Ask colleagues about their jobs
  • Learn what exists outside your current environment
  • Challenge assumptions about what is possible

4. The Legal Reality of Leaving a Job

Amanda Hill explains why impulsive resignation is dangerous.

Common contract “scorpion tail” provisions include:

  • Sign-on bonus clawbacks
  • Tail malpractice insurance obligations
  • Notice period restrictions
  • Loss of CME or vacation benefits
  • Non-compete implications

Key Message:
Your contract determines your exit strategy — not your emotions.

5. Strategic Career Transition Principles

Physicians should:

  • Understand contracts before announcing resignation
  • Maximize benefits while still employed
  • Plan timing carefully
  • Protect finances and reputation
  • Transition from strategy, not burnout

6. The 90-Day Transition Program

Dr. Vertrees and Amanda Hill introduce their collaborative program designed to help physicians:

  • Evaluate whether to stay or leave
  • Understand contracts
  • Develop negotiation skills
  • Create strategic transition plans
  • Gain community and expert guidance

Program Details

  • Weekly sessions: Tuesdays at 6 PM Central
  • Duration: 3 months
  • Small group format
  • Includes personalized guidance and recordings
  • Founding member support continues beyond the program

Real-World Success Stories

Dr. Vertrees shares examples demonstrating the power of strategic action:

  • Negotiated significant compensation increases for herself and partners
  • Built a successful private practice after believing recruitment would be impossible
  • Found professional fulfillment through intentional career design

Key Lesson: Money alone does not fix misalignment — clarity and agency do.

Action Steps for Listeners

✅ Locate and review your employment contract
✅ Identify clawbacks, tail insurance, and notice provisions
✅ Complete the Three-Step Job Analysis
✅ Explore possibilities beyond your current environment
✅ Avoid impulsive resignation decisions
✅ Register for the free training: Protect Yourself If You Must Leave Your Job

Core Takeaways

  • Leaving a job is not failure — it is strategy.
  • Your greatest professional power is choice.
  • Most physicians wait too long to seek guidance.
  • Understanding your contract is career protection.
  • Fulfillment comes from agency, not employment status.

Connect & Learn More

Follow the BOSS Business of Surgery Series for education on the topics never taught in residency:

  • Career strategy
  • Negotiation
  • Leadership
  • Professional fulfillment