My Most Embarrassing Moment

The malpractice carrier answered on the first ring. I called from the car, having just left the courthouse. I told the client things would get fixed—somehow.

I’ll tell you what happened as best as I can recall. It’s possible that the coping mechanisms in my brain have rewritten the story I tell myself. I have no idea whether every detail of this is exactly what happened. It’s all fuzzy and covered in years of emotion, denial, and the retelling of the events.

Here we go:

I was trying an alimony case. It was my first trial after I’d returned from my heart attack. Maybe I was rusty?

I represented the dependent spouse. We wanted the alimony. We had to prove some basic elements (fault, dependency, and the other spouse’s ability to support my client). I’d made my opening statement, I had offered my client to testify on the numbers, and, if I recall correctly, we had stipulated on fault (so no evidence was required).

However, I was required to present evidence of my client’s income, expenses, assets, and debts. I had to do the same for the other party. That would pretty much do it for my case in chief. I had to lay out the finances of the family.

I had my client testify. She was cross-examined after I finished with her. I didn’t call the other party. I had offered our financial evidence, but I didn’t offer the evidence related to the other party. I rested my case.

The opposing counsel rose to make what I thought was a routine motion to dismiss at the close of my evidence. He blabbered on, and I realized there was nothing routine about what was happening.

A bit of backstory: In our county, the usual practice is for the attorneys to meet before trial and stipulate to allow the moving party to skip the evidence that’ll come from the opposing party. We usually stipulate that we can bring out that evidence on cross-examination during the opposing party’s case. That way, we don’t have to call the opposing party during our case in chief. I’d done it that way lots of times. I was used to it. It was my routine.

The problem on that horrible day was that we hadn’t stipulated on that point. I’d never brought it up when I talked with the other attorney, and he, smartly, hadn’t raised the issue either. I was required to offer the evidence, and I hadn’t done so. I was screwed.

I watched the judge, like it was a slow-motion horror movie, dismiss my case. Boom. It was over in an instant. I was embarrassed, but it wasn’t that bad. I was scrambling so fast trying to recover that I hadn’t fully appreciated the impact of the situation. There weren’t lots of other lawyers around, so only those in the courtroom knew what had happened.

I hadn’t yet had a chance to calculate the damage I’d caused by multiplying monthly alimony times the potential lifespan of my client (who would have likely been awarded alimony for life). I hadn’t fully appreciated that the alimony could amount to millions of dollars over years of payments.

I met with my client and baffled her with my best bullshit. I was stunned, but not so stunned that I couldn’t keep massaging her and making sure she stayed calm. The survival instinct kicked in. We’re good at damage repair, and there’s nothing like the scrambling most of us do when we’re the one on the line. I was in full-on autopilot defense. I hadn’t processed what had happened.

Then I got into the car and headed back to the office.

That’s when I called the malpractice carrier.

A Call for Help

That wasn’t something I was likely to do. I’m the kind of guy who believes I can fix things. I’m inclined to keep my mistakes to myself and fix them before anyone else figures them out. I don’t like being embarrassed by my errors. The idea of calling someone for help is not something that normally pops into my head.

I have no idea why I called the insurance company first. I hadn’t even run the situation by any of the lawyers in my firm. I hadn’t even made it back to the office yet to settle down. I just dialed up the company on my cell phone.

We use Lawyers Mutual Insurance Company. People can say what they like about insurance companies, but I’ll tell you that I fell in love with our insurance company on that day.

I told the representative my story, and the rep told me what to do and what to say. The rep reviewed the situation and quickly decided we needed counsel. I met with the attorneys the insurer hired and felt much better as they developed a plan for repairing the situation.

Time passed, I lost sleep, and we finally appeared in front of the judge we’d had for the alimony hearing. The insurance company lawyers filed a motion for reconsideration and had me sit in the front row to watch as things played out. That was a very weird, unpleasant, and horrible few hours.

I sat in the courtroom, head spinning, as other lawyers came and went, going about their daily business. Several lawyers asked me what was happening as the hearing progressed. Of course, they had no idea it was a hearing about how I’d screwed up. I could barely answer their questions in my nearly catatonic state. The whole experience was horribly traumatic. My heart was pounding. My anxiety level was through the roof. Just thinking back to that day makes me queasy now.

Each time the courtroom door opened, I turned beet red. One lawyer, an especially kind lawyer who figured out what was happening and said something nice to me, helped make the experience a bit less horrible. But it was pretty awful having my mistake examined in painstaking detail by the court and counsel for both sides.

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The judge listened attentively. I’d already concluded that the judge, the same judge who had ruled against me at the close of my evidence, was not going to reverse himself. I assumed we were going to go through the motions and that the case would then get appealed, we’d lose, I’d get sued for malpractice, and this would drag on for years. The judge took the case under advisement. We left the courtroom, knowing it could be a while before he handed down his decision.

Days passed. Anxiety grew. I had to keep doing what I had to keep doing. I just kept going and tried not to think about the brewing mess.

The next week, the judge ruled. Miraculously, he granted the motion, and the situation was fixed. The case moved forward, got settled, and our client got what she deserved. I was thankful to be off the hook. After my embarrassment dissipated, I was thrilled that my client wasn’t harmed by my mistake.

I had been saved by the lawyers provided by the insurance company. I love those lawyers. I still remember them fondly.

Making mistakes is terrible. It’s awful for you, and it’s even worse for the client. However, mistakes can be fixed if you handle them well. Thankfully, in a mostly out-of-character way, I got the help I needed to get this situation repaired. The quick call for help got me out of trouble and solved my client’s financial problem.

What To Do When You Make An Embarrassing Mistake

1. Put the client first.

For you, putting the client first may come naturally. That’s tough for me when I screw up. I immediately worry about me, and that distracts me from my primary mission of protecting my client. That’s not only unprofessional, but it’s also counterproductive. Putting the client first helps us manage our own emotions. It’s easier to stay on track when we’re protecting someone else’s interests rather than our own. Fixing it for them is a higher calling and reorients our focus.

2. Mistakes are inevitable.

It’s sad, but there’s no way to keep from screwing up at some point. We handle complicated situations involving lots of moving parts. We make mistakes, we miss deadlines, and we get confused. It’s unavoidable, and it’s coming for you at some point. Do your best to prevent mistakes, but be prepared to manage them when they happen. Don’t let the mistake paralyze you.

3. Ask for help.

It’s not just insurance companies that will come to your rescue. You can get help from your colleagues and friends. Share the burden and allow others to be of assistance. Don’t hide it, cover it up, and keep it a secret. Let those you trust come to your assistance by informing them, asking for assistance, and taking what they offer. You need the help at times like these, and they’re willing to be there for you. Don’t limit the help you seek to the professional. Making mistakes results in psychic trauma. Be open to accepting emotional support as well.

4. Embarrassment passes.

It might not happen overnight, but the embarrassment that comes from screwing up will pass. With each day, the sharpness of the issue diminishes. Your face will burn a little less red with each mention. At some point, you’ll start to see the lessons you learned. Making mistakes and suffering the embarrassment are teachers with power like nothing else. These lessons are seared into your brain.

5. Build systems.

We build systems for everything. We’ve got a process for taking credit cards, arranging depositions, and preparing trial notebooks. Do you have a system for managing your mistakes? When the mistake happens, do you know who to call, what to say, and how to proceed? You know mistakes are coming, and the system needs to be in place before it happens. Being under stress, without a plan, results in more mistakes, which complicates the underlying issue. Build the mistake system now.

6. Learn and teach.

Yep, mistakes sear their lessons into your brain. However, be sure to maintain your awareness of those lessons by sharing the lessons with others. That keeps your learning fresh and reminds you of the inevitability of mistakes so you can be prepared for the next one. You lessen the impact of your mistakes by learning from them, sharing those lessons, and using the bad experience to add more good to your universe. Teach your associates, your colleagues, and others what you learned. Passing it along mitigates the overall impact of the bad stuff by balancing it with good stuff.


Looking back on my mistake, I’m kind of amazed that I immediately made the call to the insurance carrier. That was totally not what I would have thought I’d do. It turned out to be a fortunate way to handle the situation. My insurer gave me great advice, wise counsel, and fixed the situation. I’m not sure how I got around my instinct to cover it up and fix it myself. I’m just lucky that instinct didn’t win out.

I just hope the lessons I learned from this mistake will inform the way I handle the next one. I hope my instincts don’t take over and cause me to make my next problem worse instead of better. I have to keep having that conversation with myself so I’ll be ready.

Mistakes are coming. They’ll happen to you, your associates, your colleagues, your friends, and your family. Now is the time to get ready. They’re coming.

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