Is That Deductible? It Depends: "Breakfast With Dan"

by Tod Stillson MD

Hometown Friendship

Dan and I have breakfast once a month at a local diner.He is not just a childhood friend, but also a connection that has stood the test of time. He is a treasured life companion who has been there for me through all the ups and downs. He stood by my side at both of my weddings. He was right there beside me when I had to bury my first wife, who tragically succumbed to breast cancer at the young age of 33. This devastating loss made me a widower with two children under the age of 3. Interestingly, when he met his wife, after being single well into his 30s, I provided pre-marital counseling and officiated his wedding. In fact, I even had the privilege of delivering each of his children.

Predicament

He is the kind of friend who will bail you out of any predicament. For example, there was this time when I was on a date with my future second wife. Let me set the scene for you: I live a couple of hours away from Chicago in a rural area, and there is a train service that takes you downtown. Ellen, who would later become my second wife, and I decided to have an epic date in the bustling city. We caught the first train at 6 am, explored all the iconic landmarks Chicago has to offer, and planned to catch the last train out of downtown at midnight. I had to work the next day, but that was irrelevant in the midst of this big adventure. However, just like in a Cinderella-like moment, everything changed when the clock struck midnight. As we approached the train station deck, we saw the train pulling away without us. Ellen giggled, and I immediately felt a sense of panic. As two highly conservative individuals, "just getting a room" was never an option for our new relationship. I had made a promise to Ellen's parents to ensure her safe return home, and I had a clinic full of patients eagerly waiting to see me at 7:30 am. What do I do now?

Yep, I called Dan. Since he lives just 20 minutes from my home, I carefully explained the predicament to him. Without any hesitation, he kindly offered to drive to Chicago, pick us up, and bring us home—no questions asked.

Dan is the kind of friend we all hope to have in our lives! Having a friend like Dan is truly invaluable.

The Present

Fast forward to the present, and Dan has transformed into a highly successful entrepreneur. He now owns multiple food businesses, a vast portfolio of real estate, and even supports his wife who owns and operates a successful exercise studio.  It's incredible to think that he started as a schoolteacher and has now become the night court judge in his small hometown. Dan's journey is a testament to his hard work, determination, and unwavering ambition. He is the kind of guy who can flip any house and do the work himself. Despite being a wealthy man, he drives around in an old truck with literal holes in the floorboard (covered by cardboard, of course). He truly embodies the humble and unassuming millionaire next door.

During our meetings, we both look at each other, fully aware of the simplicity of our upbringing. We shake our heads in disbelief at how far we've come in life. We are financially independent, content, have thriving marriages and families, and run successful business enterprises. Our monthly meetings are always filled with engaging discussions and exciting topics to explore.

My Coach & Mentor

Taking a step back in our story, in school, Dan was a student council geek, and I was the prototypical jock. Despite our different social circles and upbringings, we became unlikely friends. My parents both worked in factories, while Dan's dad owned a local jewelry store.Back in the day, I used to consider him as "one of those rich kids," while he saw me as one of those aimless hometown lifers whose only claim to fame would come from the Friday night lights of high school football notoriety. In the small-town factories, those community-centric football games were always the talk of the town, with everyone proudly boasting about them. Everyone looked forward to attending after they got off work. If you have ever grown up in a small town, you would understand the enduring fame and hometown pride that school athletes receive.

But fate had a different plan for our unlikely relationship, as Dan chose to pursue a friendship with me. The end result was a faith-based experience of participating in a service project with his church youth group in Appalachia.In that unlikely, remote place along a mountain creek, our lives were transformed by our encounter with God. For me, it was a life-changing experience, and for Dan, it served as confirmation of the powerful faith community he was already a part of. I could see that Dan knew the way, so I eagerly tucked in and followed him, soaking up all the knowledge and wisdom he had to offer.

This set in motion a social structure that continues to exist to this day. Dan serves as a mentor, coach, friend, and a mutual pursuer of truth.

He is not just any fan, but my biggest fan. He diligently reads every blog I write and is genuinely curious about it all, even though he is not a physician. It truly takes a special friend to faithfully read and show interest in this content about doctors!

Senior Omelet

Dan and I are the type of wealthy people who appreciate the value of even the smallest things. We would pick up a penny from the ground and savor it as if it were a precious treasure for the day. We understand the worth of a dollar and it is something we have never forgotten.

With our graying hair, when we sit down at the diner, we can now both order the discounted "senior omelet" and save a few bucks. It truly delights us to do this, not only because of the money saved but also because we can't believe we've reached that stage of being "that old" now.

As we wrap up our meeting, during which we mutually discuss all that life has given us in the previous month, we schedule the next one. We then take turns paying the bill, faithfully alternating this responsibility each month.

Dan is not only my business coach but also my life coach. We are fellow entrepreneurs, supporting and uplifting each other on our holistic journey towards living our best lives. I truly treasure his valuable insights, advice, and unwavering support. Together, we sharpen and inspire one another to reach new heights.

For example, this week he said to me unsolicited, "I love how you are combining Dr. Incorporated with SimpliMD and now offering your SimpliMD members an entire menu of products that range from free to paid. This online store is an excellent way to support their micro-corporations.” As a former educator, he is enthusiastic about the idea of me creating courses for our SimpliMD community.

Is It Deductible? It Depends

When I go to pay for our breakfast this week, is it deductible? Should I use my corporate credit card or a personal one?

I choose to enter this as a deductible business expense and utilize my corporate card.

Why? Because of the invaluable business and life coaching that Dan provides to me, all for the simple cost of breakfast every other month.

We All Need Coaches

If you don't have a Dan in your life but you know that you need some holistic business coaching, I invite you to sign up and let me provide individualized coaching for you. I offer annual coaching programs that range from quarterly (which I call 4-packs) all the way through monthly (which I call 12-packs). Having a coach in our lives is essential, and I believe in the value it brings. Plus, you'll be happy to know that our coaching program is a deductible business expense for you!

You can also delve deeper into coaching by downloading my free guide on "Why Doctors Need Teachers, Mentors & Coaching".