Is That Deductible? Strategic Planning Retreat: Crafting the Vision for 2025

The Power of Reflection

Each year, my wife and I set aside time for our annual strategic planning retreat—a deliberate pause to reflect on the past year, envision our future, and align our goals. It’s more than just a planning session; it’s a transformative ritual that integrates personal and professional priorities into a cohesive vision.

This year, we chose Fort Worth, Texas, as our retreat destination, coinciding with a deeply personal milestone: the birth of our first grandchild, Wilder. Holding this new life in our arms brought an unmatched clarity to our discussions about legacy, purpose, and the future.

The retreat wasn't just about celebrating milestones; it was about crafting the next chapter. It reminded me of the sentiments I shared in last week’s blog post, "Wilder Beginnings," where I discussed the importance of embracing new opportunities with intention.

Strategic Planning: Dare to Dream

Our retreat was guided by a framework I call Dare to Dream, a planning template I’ve shared with the SimpliMD community. You can download it here for free. This tool helps us reflect on the past, envision the future, and create actionable steps to achieve our goals. Over several days, we worked through the template, balancing big-picture dreaming with detailed execution.

Here’s how the process unfolds:

1. Reflection We assess the wins and challenges of the past year. For example:

   • Our South Haven short-term rental (STR) achieved its best performance ever, generating nearly $100,000 in revenue.

   • We wrapped up a 20 year old real estate development in our community that created affordable housing working class citizens.

   • We celebrated a major milestone: becoming entirely debt-free in both personal and business finances. This achievement provided us with the freedom to dream bigger.

   • One of our daughters got engaged, our first grandbaby was born, and two of our children purchased their first home all of which were wonderful moments to reflect on.

   • We adventured and explored 7 US National Parks and had spectacular trips to Australia, New Zealand, and Egypt this year.

   • I wrapped up my nearly 30 years of rural FM-OB work at little clinic and retired into “semi-retirement”

   • I was able to innovate & create a patented FDA approved medical device that will help millions of people in the US.

2. Goal Setting We establish both personal and business aspirations for 2025. This next year, our focus distilled into five guiding words: Support. Build. Explore. Expand. Cherish.

   • Support: My wife’s passion for scrapbooking and our family milestones.

   • Build: My new start-up, ChatRx, into a thriving enterprise.

   • Explore: The world together, with planned trips to Antarctica, Iceland, and Ireland.

   • Expand: SimpliMD to empower more physicians through micro-business ownership.

   • Cherish: Precious moments with our family, especially with baby Wilder.

3. Budgeting Every goal must be underpinned by a budget. We reviewed both personal and business finances, aligning our resources with our vision. This included planning corporate distributions, allocating funds for new initiatives, and fine-tuning our tax strategy.

4. Evaluation With 10 businesses in our “enterprise,” we evaluate each one’s performance, profitability, and alignment with our overall goals. The insights gained inform our decisions for growth or pivots in the upcoming year.

Why It’s Deductible: The Business Case for Reflection

One common question about trips like ours is whether they qualify as deductible business expenses. The answer? Absolutely—when structured properly, including an agenda and notes. Our retreat, for instance, was a formal business planning event for our enterprises, expensed through our business development company.

I am deeply convinced that for physicians, in particular, breaking free from the relentless demands of work & home is absolutely vital. This essential separation not only fosters clarity of thought but also provides invaluable time for profound and mindful self-reflection. It's a crucial step towards rejuvenating their spirit and enhancing their ability to heal others with renewed passion and insight.

The necessity for separation is the reason my strategic planning retreats are frequently held in states other than my home state. Over the years, I have conducted these retreats in various locations, including Illinois, Michigan, Hawaii, California, Florida, and currently Texas

Conducting a business planning retreat midway through the fourth quarter of each year is a strategic approach. This timing allows for sufficient data collection on the business's performance, enabling informed decision-making. Additionally, it provides an opportunity to align any necessary adjustments with quarterly tax planning, ensuring a cohesive and efficient strategy moving forward.

• Covered expenses: Flights, suite hotel accommodations, car rental, meals, and time spent on strategic planning.

• Tax timing: Conducting the retreat just before our quarterly tax planning meeting in December ensures our strategies align with tax compliance and optimization.

This dual-purpose approach—personal time combined with a business agenda—maximizes both time and financial efficiency.

Pro Tip: If you’re self-employed, work with a CPA experienced in micro-businesses to navigate the intersection of personal and professional expenses. SimpliMD members have access to a network of vetted CPAs who specialize in this area.

The Benefits of Strategic Planning for Physicians

For physicians managing micro-corporations, finding and dedicating specific time for strategic planning is not just a beneficial luxury—it's an absolute necessity. As self-employed professionals, you juggle multiple roles simultaneously: the skilled practitioner providing care to patients, the entrepreneur overseeing business operations and ensuring financial stability, and the visionary looking toward future growth and innovation.

Each role demands attention and focus, often pulling you in different directions. A retreat designed for this purpose offers a rare opportunity to step back from daily responsibilities and distractions. It provides the much-needed clarity to thoughtfully align your professional endeavors with your broader life’s purpose. This focused environment fosters deep reflection and allows you to reassess priorities, ensuring that your work not only meets immediate needs but also contributes meaningfully to long-term goals.

Tools to Simplify Your Planning

SimpliMD offers a comprehensive Micro-Business Plan Bundle designed to make your planning process seamless:

• SimpliMD Business Plan Template A step-by-step guide tailored for self-employed doctors.

• Micro-Corporation Budget Template Save hours of time by organizing your finances effectively.

• SWOT Analysis Template Identify strengths, weaknesses, opportunities, and threats to optimize your strategy.

Your Next Steps: Build Your Future with SimpliMD

This retreat reaffirmed the importance of intentional planning in both life and work. If you’re inspired to take control of your professional journey, here’s how SimpliMD can help:

1. Personalized Micro-Business Consult Book a consult for just $99, which includes a one-year SimpliMD membership (a $2,500 value). You’ll gain access to exclusive business resources, templates, and expert advice to help you thrive as a self-employed physician.

2. “Creating a Practice Without Walls” Enroll in my course and learn how to transition into self-employment. This course empowers you to create a micro-corporation, providing the tools to navigate the marketplace with confidence and autonomy.

3. SimpliMD Business Plan Bundle Download this essential toolkit to streamline your planning process. It’s designed to save you time, enhance your strategy, and position your micro-corporation for success.

Closing Thoughts

This trip to Fort Worth was a vivid reminder of the harmony that can exist between personal and professional pursuits. From holding our first grandbaby, Wilder, to shaping the vision for our future, this retreat underscored the joy of building a legacy—whether it’s through family or enterprise.

Let SimpliMD help you craft your own legacy. Book your consult, enroll in our course, or download the Business Plan Suite today. Start building a life of freedom, fulfillment, and financial success.