What a Little League Season Taught Me About Owning My Professional Life.

The Entrepreneur's Life

What a Little League Season Taught Me About Owning My Professional Life.

About fifteen to twenty years ago, I coached my son's little league baseball team. I also sponsored it which meant our family name went on the jerseys, which my son considered roughly the greatest development in the history of organized sport. I have been thinking about that season lately. Not because anything in particular brought it to mind, but because I find myself telling the story more often when I talk with physicians about why professional autonomy matters and I realized I have never actually written it down.

So here it is. The story of one baseball season, and what it revealed about the professional structure that made it possible.

Tuesday Evenings at the Diamond

Games were mostly on Tuesday and Thursday evenings, with Saturday mornings scattered through the spring schedule. Practice was Tuesday afternoons. For four months, I was on a baseball field with a group of eight and nine year olds, teaching them to field ground balls, time their swing, run the bases without overthinking it, and above all remember that this was supposed to be fun.

Ellen came to every game. That was not a small thing, and I knew it at the time. When your spouse shows up to every game not because they felt obligated, not because they were counting the hours, but because they genuinely wanted to be there, you felt it. The kids felt it. The other families felt it. Ellen had a spot in the bleachers she returned to every time, and the consistency of it the fact that you could look over from the third base line and know exactly where she would be was its own kind of steadiness. What was even more amazing was that she was managing 4 other kids while in the stands, and this feat still impresses me today!

My extended family rotated through the stands across the season. There were games where our section of the bleachers was louder than every other section combined, not because we were organized but because the people there actually wanted to be there and were not waiting for it to end. After games, the team got ice cream. The kids stood in the parking lot in the early summer evening light and reconstructed every play with the detail and passion that only eight year olds can summon for something that happened forty minutes ago. I stood among them in my coaching shirt, covered in infield dust, listening to the argument about whether the close play at second was safe or out, and I thought: this is exactly what I worked to be able to do.

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Why I Could Be There at All

I want to be honest about something. I could not have coached that team if I had still been working inside a traditional employment arrangement. Not because my former employer was uniquely hostile to family life. But because the structure of traditional physician employment the scheduled clinic hours set by someone else, the productivity expectations that expand to fill every available hour, the call obligations that arrive without regard for what else is on your calendar does not leave the kind of reliable, predictable open space that coaching a youth sports team requires.

Coaching is not a one-time commitment. It is showing up Tuesday afternoon for sixteen consecutive weeks, reliably, whether the rest of your week was hard or easy, whether you are tired or full of energy. You cannot do that on a schedule you do not own. You cannot make that commitment when Tuesday afternoon can be claimed by the institution at any point for any reason they determine is more pressing.

By the time that baseball season happened, I had already made the transition to an independent contractor arrangement through my professional corporation. I set my clinical hours. I held time on my calendar for the things that mattered to me outside the clinic, and those commitments were protected with the same discipline I applied to professional ones. I left for practice at the same time every Tuesday. My patients were well cared for. My son had a coach who showed up.

The physicians I knew who earned more than I did but worked inside traditional employment arrangements could not have made that commitment with any reliability. Not because they were less dedicated fathers or less committed to their families. Because they did not own their Tuesday afternoons. I did. The difference was not the income. It was the structure.

The most valuable thing physician entrepreneurship gave me during those years was not on any tax return. It was time: specifically, the ability to decide how it was spent and to hold that decision against the institutional forces that would otherwise have filled it for me.

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What My Son Got From That Season

My son was at an age where a father's presence or absence at the things that mattered to him was being registered and filed away in a way he would not be able to articulate for another twenty years. I knew this, because I had been that age once, and I still remembered not the specific games, not the scores, but the texture of whether the adults who were supposed to show up had shown up.

I was there. Not in the bleachers, watching from a distance. In the dugout. Calling the lineup. Crouching behind a kid at the tee and helping him think about keeping his hands through the zone. Losing my voice calling encouragement at a routine ground ball that somehow became a two-run adventure involving every fielder on the infield. Being the adult who ended Tuesday evenings covered in dirt and would not have traded any of it.

Looking back fifteen to twenty years later, what I know is that the specific plays are gone. My son does not remember the score of most of those games. But he remembers that I was his coach. He remembers the jerseys with our name on them. He remembers that his father was the person in the dugout, not the bleachers present, invested, covered in the same dust as the rest of the team. That is a transaction that cannot be completed on a different timeline. You cannot go back and coach the season that already happened. There is only one version of it, and either you were there or you were not.

I was there because I had built a professional life that left room for me to be.

What the Family Got From That Season

Ellen and I have always held the same belief about where the return on a life actually shows up: in the experiences you build together, not in the balance sheet you leave behind. Our adventure list, the trips we have taken, the summers at Simpli SoHa on Lake Michigan these are all expressions of the same conviction that the life built alongside the career is the point of the career, not its byproduct.

Baseball season became something the whole family organized around that spring. There was a rhythm to the weeks with games, the preparation, the drive out, Ellen's spot in the bleachers, the particular energy of a Thursday evening under the lights. Other family members built the games into their own schedules across the season. Our section of the stands held people who had chosen to be there, and the choosing made all the difference. You could see it in how the kids played when the bleachers were full of people who were genuinely paying attention versus the games where the stands were half-empty and the families who were there were somewhere else in their heads.

My son played loose that season. He swung freely. He made mistakes without freezing up after them. He celebrated the good plays with the uninhibited joy of a kid who is not carrying any anxiety into the batter's box about whether the people watching him are glad to be there. They were glad to be there. He knew it. It showed up in how he played.

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What That Season Taught Me About Wellbeing

I think about that baseball season now when physicians in coaching sessions tell me they are burned out. I ask them what they have given up. Not professionally, I know they have given up professional satisfaction and autonomy and the sense of meaning that comes from practicing medicine on your own terms. I mean personally. What have they stopped doing because the schedule does not leave room for it? What commitments have they made and then broken because Tuesday afternoon got claimed by something the institution decided was more important? What version of their family life have they settled for because the professional structure they work inside does not leave room for the one they actually wanted?

The answer is almost always the same. They gave up the things that made them whole people outside the clinic. The coaching, the travel, the season tickets, the Tuesday evenings that belonged to the family. They did not give those things up because they stopped wanting them. They gave them up because the employment arrangement they entered demanded everything and made the rest feel like something to get around to when things settled down which they never did.

I was fortunate to have figured out early enough that things were not going to settle down on their own. The professional life that leaves room for a Tuesday afternoon at a baseball diamond does not happen by waiting for your employer to offer it. It happens by building a structure that produces it by owning your schedule, by designing your clinical commitments around your life rather than designing your life around your clinical commitments, and by refusing to accept the premise that the years when your children are young and want you present are the years you have to be least available to them.

My son is grown now. That little league season is fifteen to twenty years behind us. But I still have the team photo from that spring: a group of dusty, grinning eight-year-olds in jerseys that had our family name across the chest, squinting into the June sun with the particular satisfaction of a team that played hard and got ice cream after. I am in the back row in my coaching shirt, equally dusty, equally grinning.

That photo is one of the things I would point to if someone asked me what professional autonomy actually produced in my life. Not the tax savings. Not the retained income. That photo, and the Tuesday evenings it represents, and the version of my son's childhood that it was possible to have because I had built a professional life that belonged to me.

Is This Deductible?

Team Sponsorship Costs Through Your S-Corp

Potentially deductible advertising and community goodwill expense

The scenario: You sponsor your child's Little League team through your professional corporation. Your practice name appears on the jerseys and team materials. The sponsorship cost is $500. Can this run through your PC as a deductible business expense?

The ruling: Potentially yes, with qualifications. Sponsorship costs that provide genuine advertising value your practice name visible to community members who are current or potential patients can be deductible as advertising or marketing expenses under IRC Section 162 when paid through your professional corporation. The business purpose must be real: if your name on the jersey puts your practice in front of families in your patient community and generates goodwill and name recognition for your clinical work, that business purpose exists. Pay from your S-Corp business account, document the business purpose, and keep the sponsorship agreement or invoice.

The nuance: The IRS looks carefully at expenses that blend business and personal benefit. A sponsorship where your practice name appears prominently and the community connection is genuine particularly if you see patients from the families in the program is on solid ground. A sponsorship where the primary purpose is your child's participation and the business name is incidental is on weaker ground. Discuss the specifics with your CPA. The business purpose case is strongest when you are visible in the community as the sponsoring physician and you have an existing patient relationship with families involved.

For guidance on S-Corp marketing and community sponsorship deductibility, see the free eBook Tax Deduction Guide for Micro-Business Owners (PEA Explorer) and connect with DocWealth

Join the movement

I tell the baseball story in coaching sessions now because it is the most concrete illustration I have found of what professional autonomy actually produces in a life not as an abstraction, but as a specific Tuesday afternoon that either happened or did not happen, and that cannot be recovered once it is gone.

If you are a physician whose children are young right now, and whose schedule does not belong to you, and who is measuring your professional life against a vision of what it was supposed to look like the time to build the structure that changes it is not eventually. It is now. The seasons do not wait.

The Dare to Dream guide is where to start if you have not yet put language around what you actually want your professional and personal life to look like. It was built specifically for physicians who are ready to think deliberately about both dimensions together rather than treating the career as the plan and the life as whatever fits around it. Free for subscribers.

Book a $500 Business Strategy Session when you are ready to map the specific structural moves that would give you the scheduling autonomy to show up for the things you are currently missing. Join the PEA community at $99/year for Explorer membership. The physicians in this community built professional lives that left room for Tuesday afternoons. They are willing to share how they did it. The baseball diamond is not the point. The Tuesday afternoon is the point. And it is yours to have if the structure you build makes it possible.