Think that if only you didn’t work for asshole lawyers, you would like your job? Well, maybe. But often the reason you work with assholes is because their bad behavior reflects some unexamined beliefs you are holding close to your heart.

And while those beliefs are dysfunctional, their dysfunction is hauntingly familiar. In fact, it’s so familiar that it feels like some of life’s truths. And so you deep, deep down you believe that work has to suck. And you stay stuck in your unhappy legal career.

leering businessman
If this is your vision of success, maybe you need new glasses. Or a new attitude.

Last time, I listed six attitudes that lawyers tend to carry around as truth, when in fact they’re choices about how to view the world. Today I’m going to delve into two particularly noxious ones for lawyers: mistakes and valuing head over heart. These show up as problems both in their life and work, and not surprisingly in attorneys’ legal career search struggles.


You would think from the way lawyers react to mistakes, there’s a required 1L course on “Mistakes: Duck and Cover.” Oh, wait, that’s the whole law school curriculum. Never mind.

In all seriousness, lawyers treat mistakes like a judgment of their (and others’) worth from on high. Get the date wrong in a letter that should have gone out yesterday but didn’t because the partner sat on it? You’re a total screwup, incapable of paying attention to details.

Lawyers use mistakes as evidence, not as data. And the evidence is gathered to show that you or someone else is deficient, is not enough. A healthier, and more productive, way to use mistakes is as a learning tool. As in, “Well, that process/approach/idea didn’t work, so I wonder what would?” Detach from the guilt and the judgment of the evidence approach to mistakes. It wastes your energy and doesn’t get you anywhere. A way to short-circuit other people bent on charging you with the crime of a mistake is to ask them, “What do you want me to do right now to fix it? I’m thinking x, y or z might work. What do you think?”

Dealing with Interview Mistakes

But that’s actually a lot easier situation to control than your own indicting thoughts, isn’t it? Suppose you said something ridiculous in an interview that now makes you cringe. I know a lot of you will immediately start beating yourself up with the stick of “oh my God how could I be so idiotic??!!!” 

OK, you can’t change the stupid interview slipup. But instead of using the guilt stick, you could examine why it came out. Lack of preparation? You could prepare more and think ahead about the hard questions you’re praying don’t get asked. Maybe a part of you really, really didn’t want the job, but you ignored that voice? Or possibly the interviewer reminded you of the horrifying partner you worked for once, and made you nervous? The whole place gave you the creeps and set you on edge? Maybe you dodged a bullet through your supposedly stupid comment.

We always learn more from our mistakes than our successes, because we usually don’t know exactly why we succeeded. We think we do, but often find out we were wrong—because we fail at the same thing later and then see why we really succeeded the first time. 

That’s why the military uses after action reviews—they examine both what went well, and why, along with what didn’t go right, and how it can be fixed, prevented or improved next time. Blame is not part of the equation in those reviews. Bring that attitude into your life, and watch your job search take off.

Valuing Head Over Heart

Law is, not surprisingly, filled with people who prefer cool, detached thinking over using gut feelings, instincts or hunches. And, our culture reinforces the notion that you should conduct your life with flowcharts and risk management tools. Trouble is, those instincts you ignore and dismiss are often right on the money, but their truth doesn’t match up with what we think of as truth. That deeper part of us knows our real truths, and frankly couldn’t care less about how the stock market is doing, or how neat your house is, or what your family would think if they knew. Truth is more enduring than that.

There’s a crystal clear path between this thinking preference—the T in the Meyers-Briggs alphabet soup—and lack of innovation. It’s pretty difficult to make a compelling logical, lawyerly case for businesses like Google, Twitter, or Facebook in their nascent phase. Or remember when everyone was saying last rites over Apple in the 90s? Committing to those businesses was a leap of faith. Now, they all dominate our lives in ways we (and they) couldn’t envision a mere decade ago.

“But,” you’re thinking, “I don’t need to innovate, I just need a job that I don’t hate!” Well, like it or not, finding such a job does require innovation and risk on your part. Or you’ll just end up with the same damned boring job with maybe slightly less toxic colleagues. (That’s the best case scenario, incidentally.)

If You Want Change, Ditch the Logical Path

In an alternative legal career search, here’s what valuing head over heart looks like: wanting a linear, logical path, with readily identifiable markers of progress. It’s being more focused on salary, stability and benefits than worrying about whether a particular career excites you. Oprah could have remained a TV reporter, but she chose instead to follow the passions of her heart. Seems to have worked out OK for her. Yet she had no guarantees when she started down her new path. Zero, zippo, zilch. A lot of her colleagues and friends thought she was certifiable.

Connecting with your heart, your purpose, is where your future lies. So listen to those weird hunches with an open mind and heart. It may take a little while to discern what your heart is saying—after all, it hasn’t been listened to in a while. But keep at it, and your heart will start speaking up, loudly.

Not sure how to connect to your heart? Check out a couple of my older posts (here and here) on that–or drop me a line at I’d love to chat.

Jennifer Alvey is a recovering lawyer who coaches unhappy attorneys on ditching their toxic attitudes to find career happiness. Find out what that’s like with a discounted sample coaching session. It’s an hour that can change your life. Email to schedule yours today.