“The thing nobody warned me about was how fast the courtroom shrinks once you're on your feet: your notes, your eloquence, your whole theory can vanish the second a judge asks a question you didn't rehearse. I learned to script not just what I wanted to say, but the ten worst questions I could be asked, because cross-examination and judicial interruptions are where first cases come apart.”

“You are probably over-prepared on the law and under-prepared on your own nervous system. I tried 200-plus cases, and the ones I lost were rarely because I didn't know the facts; they were moments when surprise, a bad ruling, or a hostile witness got under my skin and I started reacting instead of listening.”

“I remember walking into my first immigration court case thinking the law was the hard part, and it is, but what flattened me was the human being sitting next to me whose whole life turned on every word I said. You are probably over-prepared on the facts and under-prepared for the fear in the room, including your own.”

“I prosecuted felonies and tried jury cases regularly before I ever walked into an ERISA courtroom, and I still underestimated how much the judge’s first impression of your credibility matters.”

“What I underestimated most in my first trials was how much the judge and jury watch you when you think nothing is happening: the pause before an objection, the way you handle a bad answer, the respect you show the court.”

“What I underestimated in my first trial was how much the judge's rhythm and the clerk's paperwork matter. I had the law down cold, but I walked in without knowing who to make eye contact with in that courtroom, and it showed.”

“What you’re underestimating is how much the argument turns not on what you planned to say, but on the one question you didn’t see coming. When I argued the Electoral College case in the Supreme Court, the justices kept pressing predictive and structural questions I couldn’t fully answer in a hundred words; the whole exchange became less a speech than a survey of weak points. Prepare for that.”

“What I underestimated at Barrett Daffin was how much the case lives or dies on the record you build before the hearing, not the argument itself. I once lost a motion I should have won because I assumed the judge had read the file; most of the time, they haven't.”

“What you are probably underestimating is how much the case will be decided by things that never make it into the briefs: the judge’s mood, the courtroom’s rhythm, which witness the jury believes for reasons no one can fully explain.”