Is That Deductible? Wilder Beginnings: Meeting Our First Grandchild

A Humbling Moment: Three Generations Together

There are moments in life that ground you, remind you of what truly matters, and leave you filled with gratitude. This past week, my wife and I experienced such a moment when we traveled to Fort Worth, Texas, to meet our first grandchild, Wilder John Stillson.

Born just days before our arrival, Wilder is the first child of our oldest son, John, and his wife, Cheyenne. Holding him for the first time was a moment of pure awe. As I cradled him in my arms, the weight of this tiny life symbolized so much more—a continuation of family, a reflection of legacy, and a future filled with hope.

As a firstborn son myself, I found myself reflecting on the beautiful symmetry of visiting my firstborn son to meet his firstborn son. The experience was a poignant reminder of life’s cycles, the bonds that connect us across generations, and the privilege of being a grandparent.

Cheyenne and John have stepped into parenthood with such grace. Watching Cheyenne care for Wilder and seeing John embrace his role as a father was deeply moving. My wife and I marveled at the wonder of it all: the miracle of new life, the resilience of young parents, and the joy that comes from witnessing your children embark on their own journeys.

The Path of Entrepreneurship: Like Father, Like Son

John’s path into medicine has been remarkable in its own right. Currently a third-year family medicine resident, he’s worked hard to balance the demanding schedule of residency while embracing an entrepreneurial mindset. John has operated his own micro-corporation to moonlight, earning $90,000 last year—an impressive feat for someone still in training.

His future goals include working as an emergency room physician, where he plans to continue leveraging his entrepreneurial skills. He values the independence, flexibility, and financial security that come with operating as an independent contractor.

As a father, witnessing John adopt these principles is deeply rewarding. Over the years, I’ve emphasized the importance of building professional autonomy and creating financial freedom. Seeing those lessons come to life in my son’s professional and personal decisions is a testament to the power of modeling and mentorship.

It's a profound realization that the values we impart to our children extend far beyond them. These values create ripples that touch their families, shape their careers, and influence future generations. Even though Wilder is just a few weeks old, I can't help but imagine how John's entrepreneurial spirit might one day inspire his son. This reflection doesn't even consider Cheyenne's own business acumen, shaped by her parents' remarkable success in antique auctions and commercial real estate. Little Wilder is poised to inherit a rich legacy from both sides.

Cherishing the Moments

While the professional milestones are a source of pride, our trip to Fort Worth was about so much more than that. It was about connection.

The early days of parenthood are equal parts joyful and chaotic, and my wife and I cherished every moment spent with John, Cheyenne, and baby Wilder. There’s something indescribably precious about holding a newborn, hearing their tiny sounds, and marveling at their delicate features.

As grandparents, we’re entering a new chapter in our lives—one filled with fresh opportunities to create memories, offer support, and play a role in shaping Wilder’s future. We’ve approached this transition with excitement, but also with a deep sense of humility. Being part of his life is a privilege we do not take lightly.

The trip also gave us time to reflect on our own journey as parents. Seeing John and Cheyenne step into their roles brought back memories of our early days with him and his siblings. It’s true what they say—the days are long, but the years are short. This visit was a powerful reminder to savor the fleeting nature of these moments.

During our time with them, we were able to be present with John on his 29th birthday, which offered a wonderful opportunity to celebrate and ponder this significant milestone in his life. As he approaches the completion of his family medicine residency, it was a moment filled with both joy and reflection on the journey ahead.

Blending Personal and Professional: Why We Could Expense the Trip

One of the unique aspects of this trip was how it allowed us to merge personal joy with professional growth. While the primary purpose of the visit was to meet Wilder, we also incorporated our annual strategic planning retreat for our business development company.

This dual-purpose approach meant we could expense the trip, including flights, accommodations, and meals. It’s a practical example of how personal and professional goals can often align in ways that enrich both. Strategic planning in a setting filled with family love and new beginnings felt especially meaningful.

For those of you who run micro-corporations, I encourage you to think creatively about how to blend your personal and professional priorities. With thoughtful planning, it’s possible to achieve alignment that benefits both aspects of your life.

Reflections on Legacy

As I reflect on this trip, I can’t help but think about the idea of legacy. It’s a word that often feels abstract, but moments like these bring it into focus.

What are we passing down to the next generation? For my wife and me, it’s more than just financial security or professional success. It’s about instilling values—resilience, compassion, independence, faith, and a sense of purpose.

John’s journey is a reflection of these values, and Wilder’s arrival has given us a renewed commitment to nurturing them. Our hope is that Wilder will grow up in a family where dreams are pursued boldly, challenges are faced with courage, and love is at the center of everything.

Your Turn: Building Your Legacy

Whether you’re a grandparent, parent, or simply someone reflecting on your own life, I encourage you to consider your legacy. How are you investing in the people who matter most to you? What values are you instilling, and how are you leading by example?

For physicians especially, this question extends beyond family. Your career choices shape not only your own life but also the lives of those around you. Choosing to operate as a micro-corporation, for example, can give you the autonomy and flexibility to prioritize what truly matters—both professionally and personally.

If you’re ready to take control of your professional life and create a career that aligns with your values, SimpliMD can help. We offer resources and support to help you build a micro-corporation that aligns with your goals, giving you the freedom to focus on what matters most.

Your Next Step: Build Your Future with SimpliMD

If you’re inspired to take control of your professional life, SimpliMD offers a personalized Micro-Business Consult for just $99. This includes a one-year membership (a $2,500 value) packed with resources, templates, and expert advice to help you thrive.

And if you’re ready to create your own micro-corporation, enroll in my course, “Creating a Practice Without Walls.” This course will teach you how to transition into self-employment, giving you the tools to navigate the marketplace with confidence and autonomy.

Conclusion

Our trip to Fort Worth will forever hold a special place in our hearts. Meeting Wilder, seeing John and Cheyenne as parents, and reflecting on the cycles of life were all deeply meaningful.

But more than that, it reinforced the importance of living intentionally—of blending personal joy with professional purpose, and of building a legacy that will outlast us.

If you’re on your own journey of reflection, I hope this story inspires you to think about the legacy you’re creating. And if you’re ready to take the next step in your career, I invite you to explore how SimpliMD can help you build a life of purpose and freedom.