'And bad mistakes? I've made a few': sharing mistakes to mentor new lawyers.

• Author: Easton, Stephen D.

"Good judgment comes from experience. Experience comes from bad judgment." (2)

Dear Young Star:

There is no sense in trying to hide it. I heard about it.

Because you are a human being, it hurts. Because you are from a generation that (thanks to the mistaken efforts of our generation that wanted to save you some of the pain we experienced as kids) grew up being shielded from failure, it hurts even more than it did for me. In fact, this might be the first time in your life you have failed, at least this dramatically and this publicly.

Until this moment, everything was going so well. You breezed through your undergraduate education and aced the LSAT. Law school was tough, but you persevered. In fact, you did quite well. Some of your buddies struggled with the bar exam, but you passed on your first attempt. Here at the firm, you have been the apple of many a partner's eye: cranking out thorough memos, propounding and answering discovery requests, taking and defending depositions, even filing motions with dynamite briefs. You have had the occasional minor setback from time to time, but nothing of this magnitude.

In fact, you were starting to feel pretty proud of yourself. That is not a bad thing. Lawyers need confidence. I was glad to see yours growing. We partners were starting to get a lot of confidence in you too, which is also a good thing. In fact, we were becoming so confident in you that we decided to let you handle that trial. But you lost.

So what are you going to do about it? That is the key question.

I am writing this note to give you some unrequested advice about answering that question--and to congratulate you.

Seriously. It takes guts to take on the risk of winning and losing. You have faced that risk. In the wonderful words of Theodore Roosevelt, you tried for "the triumph of high achievement," and failed to get it, but at least you failed "while daring greatly, so that [your] place shall never be with those cold and timid souls who neither know victory nor defeat." (3) It takes guts to try a case. Far too few lawyers these days have those guts. You do. Be proud of that.

Of course, you were shooting for "the triumph of high achievement," but you ended up with failure. There is a part of you thinking those "cold and timid souls" might be the smart ones.

Perish that thought right now.

Yes, you feel awful. Good. That means you care, and caring--really caring--not just about trials but about pursuing effective motions, cutting good deals, writing effective briefs, and even the mundane aspects of discovery requests and responses, is the key to effective lawyering. Whenever you make mistakes, in any of those aspects of our practice, it should hurt. Caring about mistakes and failure is critical to your improvement.

The most important thing is to learn from your failure. Use that excruciating pain you are feeling right now to motivate you to be an even better lawyer the next time.

You see, you are at the key moment of your career as a lawyer. The inevitable has happened. Some combination of your mistakes, bad breaks, and the big snakes (in the form of opposing attorneys, adverse expert witnesses, or judges) has caused you to lose. Because the stakes were high, it hurts. You don't have control over bad breaks or the big snakes, but your mistakes? That is something you can work on.

The first step is to own them. You cannot learn from your mistakes until you first identify them. If you are convinced that you did nothing wrong or that you only made little, inconsequential mistakes, there is no point in reading this letter. I have nothing to teach you, if you are not willing to identify and admit own your mistakes. If you are not able to identify the mistakes that contributed to your loss, simply toss this letter in the trash.

Oh yeah. One more thing. After you toss the letter in the trash, walk out the door. Don't bother coming back. It has been nice to have you here, but there is no point in having you here anymore. If you cannot learn from your mistakes, you cannot improve. If you cannot improve, there is no point in practicing law.

You made mistakes. Even if you had won the case (or, to note other contexts: prevailed in the motion, closed the deal, or won the appeal), you would have made mistakes. Nobody can do anything of consequence in the practice of law without making mistakes. Every day you practice law you make mistakes. In fact, make that every hour--or almost every hour. Our profession is so complicated, so much "art" instead of "science," that we all make mistakes, even though we try our best to avoid them. I have made some doozies, and so has every single lawyer I respect.

Own your mistakes. You cannot learn from them unless you identify them. Think back to key decisions that you made that turned out to be the wrong decisions. You now have the benefit of 20/20 hindsight. Use it. Be brutally honest with yourself. Get out a piece of paper and write down your mistakes.

Have you done that? Do you have a sheet or two (or maybe five or ten) of your mistakes? Don't read the rest of this letter until you have that list. Put this letter in your desk and work on your list. Don't come back to this letter until you have a brutally honest, thorough list of all the mistakes you made that might have contributed to your loss.

You are back. Good. That means you have your list of mistakes.

Now you can start to turn those mistakes into opportunities to do better the next time. That is the key to this exercise. After you have your list, don't stew on your mistakes. Own your mistakes, but don't dwell on them in some exercise of self-flagellation. Remember that you cannot change the past.

But the wonderful thing about life is that you can change the future. Turn your mistakes into ways to learn to do better in the future. That is the point of this note.

WHY I AM WRITING THIS NOTE TO YOU

You may be wondering why I am bothering you with this letter, now, of all times. You might also be wondering why I bothered to write it. Don't I have better things to do?

No. You represent the future of our firm and the future of the practice of law. (4) It is our profession's grand tradition to try to pass on the benefit of our experience to new lawyers. To put it another way, I like you. I care about you. I think you are a promising new attorney who could become a great lawyer. Like it or not, I think of myself as a mentor to you.

Not just you, though. Because I have been in the legal profession for quite a while, I have noticed that you are not the first new lawyer to face a crisis of confidence brought on by mistakes you made that led to a painful result. And you are not going to be the last one facing that reality. So I figured it was worth a bit of time and effort to put some thoughts about mistakes on paper. You are the first new lawyer to get this letter, but you won't be the last. Your mistakes were in the context of a trial. Others will make equally costly mistakes in negotiating, drafting, arguing, mediating, or doing all of the other things we do as lawyers. I hope this letter will be helpful, regardless of the context of the mistake.

GENERATIONAL DIFFERENCES REGARDING MISTAKES

As with everything you see in the practice of law, and, for that matter, in your life outside the law, you should consider the source carefully as you decide whether my mentoring is of any potential value to you. Like most of the other experienced lawyers in our firm, I am a member of the Baby Boomer generation, those born between 1946 and 1964. (5) We Baby Boomers are often described as "individualistic and hardworking." (6) A few of the other new lawyers in our firm come from Generation X, those born between 1965 and 1981. (7) Generation Xers are described as skeptical of authority, egalitarian, and fun loving. (8) You are one of the Millennials, those born between 1982 and 2000. (9) Millennials are described as team-oriented, confident, and entitled. (10)

So, you might be wondering, is there a point? I think there is. This note celebrates that transformative power of making, and learning from, mistakes. Although there are, of course, always exceptions, people in different generations treat mistakes differently. There are fundamental differences in generational attitudes toward making mistakes. By no means does this make one generation "better" than another. Just different. (11)

Our parents encouraged we Baby Boomers to try to become anything we wanted to be, but with the realization that pursuing goals would involve sinking or swimming on our own initiative. And sinking was a definite possibility. More than a possibility--a reality. Thus, it was okay if we "learned the hard way by being dropped into the deep end." (12) As a result, we Baby Boomers tend to make a lot of mistakes, but we also tend to recognize them, accept responsibility for them, and learn from them. Most importantly, we have come to embrace the importance of mistakes in becoming a professional. (13) It is not that we like making mistakes or failing to reach our goals. But we tend to accept mistakes and failure, at least to some degree, as inevitable to life, including life in the law.

We did not pass this attitude on to our children, though. Perhaps we were not that accepting of mistakes, and the failure that results from them, as we like to think we are. If we fully accepted those concepts, why did we work so hard to protect you--our children-- from the rough reality of mistakes and failure?

Indeed, we hovering parents tried to protect you from mistakes and failure. We raised you to believe that you would always be rewarded for effort, even effort laced with mistakes. In an effort to boost your self-esteem, we raised you to believe that mistakes, criticism, and failure should be avoided at all costs. If you struck out in tee ball, we told you to go to first base anyway. At the end of the season, everybody got a trophy, not just the league champions. (14)

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