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Is That Deductible? Strategic Planning Retreat

Oct 23, 2023

Dare to Dream

Annual planning retreats play a crucial role in setting personal and business goals. These retreats provide dedicated time and space for reflection on achievements, identification of areas for improvement, and the establishment of clear personal and professional objectives for the upcoming year.

With your demanding schedule and limited time for self-reflection, annual planning retreats provide a valuable opportunity to step back from your daily responsibilities and gain perspective on both your personal and professional life. By engaging in strategic thinking and goal-setting during these retreats, you can align your actions with your long-term aspirations. It is crucial to spend quality time with your significant other to integrate your goals and plans. However, I must admit that the doctor's component often dominates the conversation.

In addition to setting personal goals, annual planning retreats provide an opportunity to focus on the micro-business side of your professional life. You can evaluate your financial performance, explore growth opportunities, and develop strategies to diversify your income streams. By dedicating specific time to assess the micro-business aspects of your professional life, you can ensure that you are maximizing efficiency and profitability while also meeting your quality of life goals.

My wife and I have been engaging in this annual fall ritual for nearly 25 years. It is a cherished time we spend together. During this time, we typically complete our annual personal and micro-business goals and budgets. This is because goals, plans, and finances are all intertwined. In our early years, we would take a weekend getaway to Chicago or South Haven, paying for it ourselves, while grandparents watched our five children. However, with our multiple micro-businesses, this event is now being positioned as a strategic business retreat for our business development corporation.

Over the years, we have diligently saved our notes, goals, dreams, and budgets. It brings us great joy to revisit them each year and marvel at how our time away has motivated us to achieve our dreams.

I have created a free guide for you to use on your own dare to dream retreat with your significant other. This is the same guide I used this weekend.

Simpli SoHa

I enjoy fostering business synergy, and our annual retreat in South Haven allows us to achieve that by renting our own short-term rental (STR) property. This resort community is just over a 1-hour drive from our home, yet it gives us the feeling of being in a distant waterfront resort community. We absolutely adore every aspect of this three-story custom-built home! Check out this link if you want a great rental for your own dare to dream retreat!

As the owners of the unit, after our arrival at Simpli SoHa, I will take care of some basic maintenance and inventory assessments. I had been in contact with our property manager ahead of time, and he informed me about a couple of areas to inspect. The first issue was regarding our interior stairway railing, which our builder was supposed to fix. It was not designed to withstand the wear and tear of a short-term rental (STR). Unfortunately, they did not fulfill their promise to fix things, which is a common story with contractors based on my experience. When I contacted them about this, we received the usual response that led to rescheduling the week-long repair during a slow rental week in early December.

I changed some furnace filters, reconnected our Ecobee thermostats to the Wi-Fi, and identified the items that needed to be replaced after the busy season. We are always amazed at what gets stolen or taken from the unit!

Goals, Plans, Budgets

This year marks a transition for us as I plan to retire from daily clinical care at the end of June and then enter the Coast FIRE phase. Thus, we are creating two budgets this year: one will cover the first half of the year when my clinical income is still very high, and the second half will cover the Coast FIRE phase, which will become our new normal. We have made efforts to plan for purchasing any larger ticket items while my clinical income is high, and we have also worked towards eliminating all debt by July 2024. Admittedly, we could continue with the $200, 000 Simpli SoHa mortgage, as it carries just a 3. 1% interest rate. With its strong performance, it would easily allow us to pay off the debt within 5 years—however, we strongly prefer to be debt-free, so figuring out how to achieve this while managing our assets and income sources will be one of our priorities this weekend.

Speaking of mindsets, my professional transition will serve as a pivotal point in our lives, where my career will no longer be the dominant theme. Now is the time and space when my wife's goals and ambitions can take priority and align with our shared plan. My primary goals post-retirement are twofold:

  • Transitioning to an identity that is centered around "being" rather than "doing." I am mindfully taking the time for self-care and connecting with God.

  • I must guard against letting my passion for SimpliMD become all-consuming, and ensure that it does not infringe on the time and space I have reserved for my wife and me.

The good news is that we have created enough business channels that will provide the necessary income to sustain the budgeted lifestyle we have planned for the next season of life. Our annual spending is expected to be $176,000 with $25, 000 allocated to healthcare and $50, 000 for travel. Fortunately, our business has multiple active and passive income sources that will help us meet our budget plans and goals. The best part is that we don't have to touch our retirement investment accounts, and it doesn't rely on my plan to do 10–12 weeks per year of locums work—that income is mostly just icing on the cake. I still enjoy practicing medicine, so having a limited clinical workload will help me stay sharp without overwhelming me. My ultimate goal is to find locum tenens positions near national parks! (see below)

Freedom To Adventure

Our goal is to visit every US National Park and capture a picture at the entrance with our custom national park sign. While we have visited many of these parks over the years, we unfortunately don't have pictures with our sign, which may require some photo-editing later. Nonetheless, we are excited about the epic road trips ahead! And don’t worry, we know about some of the more unique places, like the Virgin Islands, Samoa, and Dry Tortugas—we have already checked off two of the three destinations, and we will be tackling Samoa during our South Pacific tour this winter.

We love to travel, and one of our goals is to visit each of the wonders of the world. We acknowledge that there are many lists available, but we are following a common list of the big ones that includes a wall hanging for checking them off. Similarly, we have a goal of visiting all seven continents in our lifetime. In line with that, we recently traveled to Europe this past summer, have plans for a safari in Africa in three weeks, will be heading to New Zealand and Australia in January, Egypt and the Middle East in November 2024, and finally, Antarctica in January 2025. In each of these locations, we’ll cover the nearby wonder of the world—it’s like a giant scavenger hunt!

Matters at Home

During our time away, it has been necessary to stay connected to important matters at home.

Due to my father's medical conditions, he has been enrolled in hospice care while residing in a local nursing home, as per his preference. Unfortunately, his health has deteriorated to the point where he is now completely bedridden.

We visited with him and my mom before coming up to South Haven, and my dad was pretty stable. However, the evening we arrived, my dad's condition worsened, and my sister had to come to town to support both my parents. Fortunately, he quickly rallied, but he is still terminally ill.

This sparked a discussion about bringing him home for his final weeks of life, and we have been coordinating the logistics for my mom, sister, and myself over the phone. We believe this will be the best decision, as it will allow our mom and dad to spend their remaining days together and cherish their time together. My sister and I are working on finding ways to support this process.

Ultimately, the decision of whether my dad wants to come home rests with him, as he preferred being in the nursing home as his health declined.

Is It Deductible? It Depends

The entire business retreat weekend, including transportation, lodging, and food, was a deductible business expense. We captured this expense with a thorough business agenda, meeting notes, decisions made, and an associated expense report. We charged our business the VBRO rate for renting Simpli SoHa.

Not only do my wife and I enjoy connecting over our dreams for the future, but it's even more enjoyable to do so in a fantastic location, especially when it can be considered a business expense. And the best part is when those expenses are paid to us! It's a win-win-win situation!

Several of our future travel plans incorporate business purposes, such as Continuing Medical Education (CME) through CME Away. During this weekend, we also had the opportunity to dream and book a non-business trip for 14 days to Scotland, England, and Ireland. We will be using our Marriott Vacation Points for this adventure, which is scheduled for May 2025. One of the highlights of our trip will be visiting Stonehenge, which is on our list of wonders of the world.


Are you interested in how you can start a professional micro-corporation and use it for your own annual strategic planning retreat. You are missing out if you are not doing this. Go here to begin the process of letting SimpliMD help you create your own micro-corporation.

Perhaps you already have a micro-corporation, but you could use some business coaching with learning how to maximize it. Reach out to me to here to start my popular 4-pack business coaching program.