Published June 22, 2026

When Winning Doesn't Feel Like Winning

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Written by Laura Lerma

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One of the more unusual roles I occasionally serve in is as a Special Magistrate in court-ordered property sales. Most people have never heard the term, which is understandable. Unless someone finds themselves involved in a serious dispute over a property, they will likely never encounter one.

In these situations, a judge may grant me authority that extends far beyond that of a traditional real estate broker. I may be authorized to list the property, negotiate the sale, and even sign closing documents on behalf of the owners. On paper, that sounds powerful. In fact, the first time I received such an appointment, I thought the same thing. If a judge has already decided the property should be sold and has granted someone the authority to make it happen, what could possibly be left to argue about? Quite a lot, as it turns out.

Over the years, I have learned that people rarely stop a sale by saying, “I refuse to sell.” Resistance tends to appear in much subtler ways. There is never a good day for a showing. The property is not quite ready. The timing is not right. The price is not high enough. There is nowhere to move. Each reason sounds reasonable on its own, but together they often reveal something deeper.

What I eventually learned sitting in courtrooms and working through these cases is that the property is rarely the real issue. By the time a matter reaches this stage, the house has often become a symbol of something much larger: a marriage that ended, a family conflict that never healed, a chapter of life that neither side is fully prepared to leave behind. That realization changed the way I view my role.

The challenge is not selling the property. The challenge is maximizing the outcome while helping people move forward with their lives. The court can grant authority. It can order a sale. It can create a legal resolution. What it cannot do is create agreement, readiness, or peace.

Recently, I worked on a case that took years to resolve. There were attorneys, hearings, negotiations, delays, and more than one attempt to sell the property. Eventually the property sold. Eventually the funds were distributed. Eventually the legal process came to an end. A few days later, one of the parties called me.

They thanked me for helping navigate the process and then shared a reflection that has stayed with me ever since. The property had value. The outcome was fair. The money mattered. Yet the money could not reimburse years of stress, uncertainty, sleepless nights, frustration, and emotional energy. It could not restore health. It could not repair relationships. Most importantly, it could not return the years that had already passed.

What struck me most was that, by almost every financial measure, they had won. The property sold. The proceeds were distributed. The legal process worked exactly as intended. Yet winning did not feel like winning.

As an economist, I spend much of my career helping people evaluate assets, returns, and financial outcomes. Experiences like this have taught me that some of life's most significant costs never appear on a settlement statement.

Perhaps the real question is not whether we won. Perhaps the question is whether the victory was worth the years it required.

Eventually, most of us find ourselves sitting somewhere peaceful, sharing a meal, a conversation, or a glass of wine, looking back at the chapters of our lives. In those moments, the calculation changes. The money may still be there. The years are not.

After more than twenty years in real estate, I have become increasingly convinced that wealth is not only about what we accumulate. It is also about recognizing what is no longer worth carrying.

Sometimes the wisest financial decision we ever make is deciding that the future deserves more of our attention than the past.

Laura Lerma

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