About two years ago, I lost a case. Badly. The jury deliberated for a few hours, and only asked one question: “Is there any way we can award both forms of damages?”
Throughout the case, I was confident in my decisions. I’d done the work. I knew the law. I knew the facts. I knew the evidence. I was prepared. I trusted that, because of all the work I had done, and because I’ve been trying cases for a while, that, in the heat of any moment, my instincts would serve me well.
But then the jury asked, “Is there any way we can award both forms of damages?”
And, every moment since the judge read that question aloud, all I could do was question every single decision that I made. I had lost, so I must have done something wrong, right?
So for two years, any time I was alone, I quietly evaluated not only my decisions, but the fallacy embedded somewhere deep within me, the failed instincts, that had caused them. I no longer trusted myself, but I didn’t know exactly why. I couldn’t put my finger on exactly what I had done wrong.
Then, just a few weeks ago, I was certain that I had figured out what it was: I spent too much time crossing the plaintiff. I had given him too much of the spotlight. My instinct to tear down every one of his false statements, inconsistencies, and errors was wrong. I thought I was turning him into a pariah, but instead I made him the star of the show, and the jury loved him for it. I, alone, had lost the case. My instincts had failed me. It was my fault.
Two days after I had finally deconstructed the architecture of my case and determined that I was solely at fault, I woke up to my phone vibrating on my nightstand.
Email.
Appellate ruling.
Jury verdict overturned.
My hands were shaking as I wiped the sleep from my eyes, mainly to confirm that I wasn’t dreaming. But I wasn’t going to be able to get back to sleep anyway, so I carefully read the opinion. Then I read it again. The court’s analysis of the record was ranging and extensive, but the evidence that most directly caused the verdict to be overturned was my cross examination of the plaintiff.
So maybe my strategy had been right all along?
The truth is that it probably doesn’t matter. Regardless of whether I had done the exact right thing or not, I had lost the jury verdict. It didn’t work. The hard work didn’t work. The decisions didn’t work. The strategy just. Didn’t. Work. It’s not that my decisions and effort don’t matter—they’re what I get paid for, and what I get paid to get right. It’s that, right or wrong, I still don’t get to control the outcome of a dispute (or negotiation, as the case may be). And, more importantly, it’s that, just because I didn’t get the outcome I had hoped for, still doesn’t mean that everything I had done was wrong.
But it also doesn’t mean I was wrong to question my decision-making. To debrief. To post-mortem what had been the most devastating verdict of my career. There are always lessons to be learned. What it does mean is that outcomes, no matter how devastating (or triumphant), cannot be the source of your confidence or lack thereof. You are going to lose when you should win. You are going to win when you should lose. In either instance, the critical issue is not the outcome—no matter how jubilant or morose—but rather the input. Because you can always improve the input. In fact, you owe it to yourself to do so.
So, win or lose, keep second-guessing, keep re-evaluating, keep learning, and keep getting better. As long as you do that, you can never really lose. Good luck.
Reprinted with permission from the January 13th edition of Texas Lawyer © 2025 ALM Properties, Inc. All rights reserved. Further duplication without permission is prohibited.
