What I Got Wrong About "Winning" Early in My Career
I graduated from Michigan State University College of Law in 2015 with a dual J.D. and M.B.A., a magna cum laude distinction, and a law review article that would eventually be cited in a U.S. Supreme Court brief. I was, to put it plainly, confident in my ability to construct an argument. Maybe too confident. Looking back now, that confidence was built almost entirely around a single metric: the strength of the legal position on paper. It took a few years of actual practice in Grayling, sitting across from real clients with real problems, to understand how incomplete that framework was.
The law review piece I published in 2013 argued that the Professional and Amateur Sports Protection Act could be invalidated on anticommandeering grounds under the U.S. Constitution. The argument was novel. It was also, ultimately, correct. The Supreme Court adopted that reasoning in Murphy v. NCAA and overturned the federal ban on sports gambling. By any academic measure, that was a win. And I won't pretend it wasn't satisfying. But that experience, as meaningful as it was, reinforced a habit of thinking I'd carried through law school: that the right legal argument, applied with enough precision, is the thing that matters most.
Early in my practice, I brought that same orientation to client work. I'd identify the strongest legal theory, map out the path to the best possible outcome, and present it. Clean. Logical. Compelling. What I underestimated was how often "the best possible outcome" looked completely different depending on who was sitting across from me. Two clients with nearly identical property disputes might need entirely different approaches. One wants to preserve a 30-year relationship with a neighbor. Another needs a clean legal ruling because a sale is stalled and time is money. The technically correct answer might actually damage the first client and be exactly right for the second.
This shift in thinking started coming into focus through my real estate and riparian rights work in northern Michigan. Property disputes here are rarely abstract. They involve families who have owned waterfront land for generations, neighbors who share a private road and see each other every summer, and business owners whose development timelines depend on resolving a boundary question before a construction season runs out. I started noticing that clients who "won" in a legal sense sometimes felt like they'd lost because the process had cost them a relationship, six figures in fees, or two years they couldn't get back. The law I applied was correct. The strategy, in some of those early cases, was not fully calibrated to what the client actually needed.
What I think now is that the legal question and the practical question are two separate conversations, and a good attorney has to hold both at the same time. The legal question is what the law permits, prohibits, or requires. The practical question is what this specific client, with this specific situation and these specific constraints, should actually do. My role isn't just to win arguments. It's to help people make sound decisions under conditions they didn't choose and often didn't anticipate. That distinction matters more to me now than it did in 2015.
My work at The Brook Retirement Communities sharpened this further. Serving as Legal Counsel, Deputy Finance Director, and Board Member for the same organization means I see the same decisions from three different vantage points simultaneously. A contract provision that looks protective from a legal standpoint might create friction in a lender relationship. A governance decision that's sound on paper might affect operational timing in ways that cost real money. That integrated perspective has made me a better attorney in private practice, because it forced me to stop treating legal analysis as a self-contained exercise.
The lesson I'd carry back to my earlier self is simple: listen longer before you start building the argument. The best outcome for a client is rarely identical to the best legal outcome in the abstract. It's the outcome that actually fits their life, their budget, their timeline, and the relationships they have to live with after the matter is resolved. That's the standard I try to hold myself to now, and it's the one I think separates competent legal work from genuinely useful legal counsel. If you're sorting through a property dispute or complex real estate matter, you can reach out here to talk through your situation.