After Twenty-Five Years as a Lawyer and Professor, I've Learned Why Good People Get Themselves Into Trouble

After practicing law and teaching for more than twenty-five years, one lesson has become impossible to ignore: most people do not get themselves into trouble because they are dishonest, malicious, or incompetent. More often, they get themselves into trouble because they are human.

That may sound obvious, but it explains far more than many people realize. During my career, I have represented students accused of academic misconduct, faculty members facing disciplinary proceedings, researchers under investigation, professionals defending their licenses, and employees involved in workplace disputes. I have also spent years teaching thousands of students, mentoring aspiring lawyers, and observing how people respond when the stakes are high. Although every case is different, the underlying patterns are remarkably similar.

The biggest mistakes rarely begin with bad intentions. Instead, they begin with ordinary decisions that seem entirely reasonable at the time. One of the most common is assuming instead of asking. People convince themselves they know why someone sent an email, made a decision, or filed a complaint. They assign motives before gathering facts. Once that assumption takes hold, every new event is interpreted through the same lens until they are responding not to reality, but to a story they have created in their own minds.

Another common mistake is believing that good intentions automatically protect us from bad outcomes. I have heard countless variations of the same explanation: "I didn't mean it that way," "I wasn't trying to offend anyone," or "I thought everyone understood what I meant." Intent certainly matters, but intentions do not erase consequences. People respond to what they experience, not simply to what we hoped they would experience. The ability to recognize that distinction is one of the hallmarks of sound judgment.

I have also learned that people often speak too quickly and think too little. Receiving criticism, an angry email, or notice of an investigation naturally creates an urge to respond immediately. We want to defend ourselves, correct misunderstandings, and explain why the other person has it wrong. Unfortunately, our first response is often driven by emotion rather than careful reflection. Some of the most damaging documents I have reviewed during my career were written within minutes of receiving upsetting news. Time rarely makes a thoughtful response worse. More often, it allows us to replace emotion with judgment.

Another pattern appears repeatedly in both investigations and everyday life. People consistently underestimate the importance of small decisions. They assume credibility is lost because of one dramatic event when, in reality, credibility is built—or destroyed—through a series of ordinary choices. Did you preserve important documents? Did you acknowledge uncertainty instead of guessing? Did you exaggerate? Did you document important conversations? Did you remain professional when others did not? None of these decisions seems particularly significant in isolation, but together they shape how others evaluate your judgment, reliability, and character.

Perhaps no lesson has surprised me more than the cost of pride. Few people enjoy admitting they were wrong, and once we publicly commit ourselves to a position, changing course becomes psychologically difficult. Instead of asking whether new evidence should alter our thinking, we begin searching for reasons to defend what we have already said. Ironically, the willingness to acknowledge a mistake often strengthens credibility rather than weakening it. The most respected professionals I have known were not those who never made mistakes. They were the ones who recognized mistakes quickly, corrected them honestly, and learned from them.

Over the years, I have also come to appreciate that people are rarely judged solely by what happened. More often, they are judged by how they respond after something happens. Anyone can remain calm when life is going well. Character becomes visible when circumstances become difficult. The way we respond to criticism, setbacks, disagreement, or unexpected challenges often reveals far more about us than the original event ever could.

Perhaps the most important lesson of all is that serious problems almost never appear overnight. They develop gradually. A conversation that should have occurred never takes place. A misunderstanding goes uncorrected. An uncomfortable issue is postponed. An email remains unanswered. A concern is dismissed as insignificant. Months later, people describe the resulting conflict as coming "out of nowhere." In my experience, it rarely does. The warning signs were usually present. Someone simply failed to recognize them—or chose to ignore them.

That observation is not pessimistic. Quite the opposite. If most significant problems develop gradually, then many of them can also be prevented gradually. Good judgment is rarely demonstrated by making one brilliant decision. It is demonstrated by making hundreds of thoughtful decisions long before anyone is paying attention. That is true in law, education, business, and virtually every other profession.

After twenty-five years as a lawyer and professor, I have become convinced that success depends less on avoiding every mistake than on developing the humility to recognize mistakes early, the discipline to respond thoughtfully, and the wisdom to learn from experience. Good people rarely get themselves into trouble because they intend to. More often, they get themselves into trouble because they underestimate the cumulative effect of small decisions made under pressure.

In the end, judgment is not revealed by the decisions we make when everything is easy. It is revealed by the decisions we make when everything becomes difficult.