The Strongest Legal Argument Isn't Always the Right One
I've been practicing law long enough to know that clients don't come to me looking for the law. They come looking for an outcome. That distinction sounds simple, but it shapes every conversation I have and every recommendation I make. As a partner at Carey Jaskowski PLC and as legal counsel at The Brook Retirement Communities, I work across enough contexts to see this tension play out constantly: the technically strongest position and the practically right strategy are often two different things.
Here's the belief I keep coming back to: effective representation means telling a client not just what the law permits, but what the law actually costs to pursue. Not in dollars alone. In time, in relationships, in energy, in opportunity. A client who wins a boundary dispute after three years of litigation may have preserved a property line but lost a neighbor, delayed a sale, and spent more than the disputed land was worth. That's a win on paper. It doesn't always feel like one.
I started developing this view in law school, where I was trained to find the best argument. And I still find those arguments. My law journal article on the Professional and Amateur Sports Protection Act argued a novel constitutional theory that was later cited in a U.S. Supreme Court brief and adopted in the Court's decision in Murphy v. National Collegiate Athletic Association. Getting there required building the strongest possible legal case from first principles. But a courtroom brief and a client conversation are different things. The brief needs to win on legal logic. The conversation needs to account for the person sitting across from you.
What that looks like in practice is this: before I tell a client what I think they should do, I try to understand what they're actually trying to accomplish. Two clients with nearly identical property disputes can have completely different priorities. One wants to preserve a relationship with a neighbor. Another needs a definitive ruling because the dispute is blocking a pending sale. A third is a business with a hard deadline and no patience for a prolonged process. The law may offer all three the same remedy. But the strategy I'd recommend to each of them would look different, because the right outcome looks different to each of them.
This carries over directly into my work at The Brook Retirement Communities, where I serve as legal counsel, deputy finance director, and board member simultaneously. In that setting, legal advice doesn't exist in a vacuum. A decision that minimizes legal risk might slow down a capital project. A contract position that protects the organization in the abstract might damage a lender relationship we've spent years building. Sitting at the intersection of legal, financial, and governance responsibilities means I can't afford to give advice from only one angle. I have to weigh all three at once, and the question I keep asking is: what outcome actually serves the organization's long-term interest, not just its legal position today.
Real estate and property litigation, which makes up a significant part of my practice, is where this philosophy gets tested most often. Easement disputes. Riparian rights conflicts. Boundary disagreements that have been simmering between neighbors for a decade. These cases can almost always be litigated. The question is whether they should be. I've sat with clients who were clearly in the right legally and still recommended we open a conversation before filing anything, because the facts suggested the other side didn't fully understand what the documents said. Sometimes that conversation resolves in two weeks what litigation would have dragged out for two years.
None of this means I shy away from a fight when a fight is what the situation requires. I've litigated in Michigan trial courts, in federal district courts, in the Sixth Circuit, and my bar admission extends to the U.S. Supreme Court. When a client needs an aggressive advocate, that's what I am. But the decision to go to war shouldn't be driven by the strength of the legal argument alone. It should be driven by a clear-eyed view of what the client stands to gain, what they risk losing, and whether there's a faster, cheaper, less damaging path to the same place.
That's the principle I'd put at the center of how I practice. If you want to learn more about my background and the areas I focus on, you're welcome to visit my about page or reach out directly. The goal, every time, is to get you where you actually need to go.