How Did I Get To Be An Unhappy Lawyer? Part 1

I’ve often pondered how it is that so many people end up in law who despise it. The level of discontent in the legal profession is really shockingly high—more than 50% of lawyers (some research here) say that given it to do over again, they would not go to law school.

cubicle farm
Schools are great at producing cubicle dwellers, but that's not who we need to be.

Part of the problem, as I’ve written about often (here and here, for starters) is that our schools and institutions don’t serve us very well any more when it comes to preparing us for the future. Schools are still mired in the idea and structure that they are preparing us all to be good little factory workers, where conformity and quantity production matter most. Of course, the actual economy hasn’t looked like that for a quarter century, and in the last 10 years alone has changed radically. We’re not even the Information Economy any longer. Now, as Dan Pink talks about quite eloquently in A Whole New Mind, we are in the economy where high-concept and high-touch rule the roost. Innovation and creativity are the valued skills, but schools aren’t teaching that. They have little idea how, because they’re too busy treating kids as commodities who must attain certain test scores.

Creativity, Killed by Schools

The upshot of this is that creative people often get disconnected from what fuels them as they go through traditional schooling. Nothing stifles creativity more quickly than conformity. Creativity is “Let’s see what happens! This could be so cool!” Conformity is “Don’t try that, you don’t know what’s going to happen. What does the manual say?”

Another sure-fire creativity-killer is neglect, which often poses as lack of encouragement of young creatives. Rather than nurturing the seeds of talent and passion, parents, educators and peers often judge nascent creativity by the performance standards of seasoned creatives. Sketches should look like Picasso, stories should sing like bestsellers, musicians should never miss a note and actors should never forget their lines or lose their composure. At the very least, kids have to be the best in their class at their art form to be encouraged at all. There’s no point in nurturing false hopes, right? Funny how it’s never a false hope to want to be a lawyer.

Sure, there are always those whose creativity is so way-out there that nothing can diminish their platinum-strong sense of purpose. They actually take the art classes (against the advice of lots of adults), try out for the school plays, are in the choir or band, or are busily writing stories.

In fact, Pink relates a really sobering story about creativity and schools: Gordon MacKenzie, a chief creative force at Hallmark Cards during his lifetime, often visited schools to talk about his profession. He would admire the artwork on the walls, and then ask, “How many artists are there in the room?”

Invariably, the kindergartners and 1st graders all raised their hands, quickly and enthusiastically. In 2nd grade, about 3/4 raised their hands, but less eagerly. In 3rd grade, only a few held up their hands. By 6th grade, not one hand went up.

“The kids just looked around to see if anybody in the class would admit to what they’d now learned was deviant behavior,” says Pink. And I agree with him when he says we shouldn’t just cluck and say how sad. We should be outraged that our schools squash such an essential aspect of our children’s humanity. Creativity is the birthright of every human being, whether it comes out as a an artist, writer, fantastic problem-solver or amazing negotiator. Or as something that hasn’t even been created yet.

Even if the humanity argument doesn’t move you, the fact is that nowadays, companies are scrambling to cultivate creativity in their workforces to solve problems that they’ve never confronted before. Those problems won’t be solved by using the hammer of conformity that worked in 1980.

Did This Happen To You?

No doubt about it, if you have a very agile analytic mind, you’re often pushed into those smarty-pants courses that you can do well in where others can’t. Highly creative people are also very curious (cf., “Let’s see what happens!”), and it’s not like they mind learning about a vast number of topics, from love and betrayal in literature classes to string theory in physics to the Bolshevik revolution. So they get A’s because they’re curious and like learning stuff, not because they’re so especially suited to that area.

I’m not saying that everyone who gets good grades is a closet poet, actor, writer, sculptor or painter. There are plenty of people who are good students with a good analytic brain who will be very satisfied in a job that requires analysis as one of its key components: scientists, financial analysts, researchers, academics, doctors, lawyers—there’s a long list of possibilities.

But we’re brainwashed in our schooling to think that analytic gifts must be used in those kinds of professions, or they’re “wasted.” Never mind that to be at the top of nearly any career, you have to have some serious brain power. Good analytic skills help you figure out what’s fueling a trend, how to connect with people on various platforms, whether it’s better to take one course of action or another. Analytic skills don’t have to be the entire focus of your job; they’ll still get good use and make you better at what you do.

The Punch-List Life Goes To Law School

There are lots and lots of incentives to pursue the punch-list path. What is the punch-list path? That’s where you get great grades, do a bunch of activities because they look good on your college applications (maybe you even like them), and don’t really question what makes you come alive. Then you do it all again, only this time you pick out a nice major in college that leads to a career your parents/society approves of. Because you haven’t explored much to figure out what lights you up–it’s all been about the punch list.

When you’re young, everything feels new and exciting. You probably didn’t have enough experience to tell the difference between that kind of ooh-shiny excitement and the excitement that fuels your soul. So without knowing exactly what you wanted to do (since you weren’t encouraged to explore, but rather to complete the punch list), and because it was a prestigious, profitable, and predictable path, you went to law school. Phase 1 of disconnecting from your dreams is complete.

Oh, but Phase 2, in which you get almost completely disconnected from yourself, is coming. More on that next time.

Now you know I don’t just whine and bitch and moan about stuff. I’ll offer some solutions for reconnecting with yourself, and your dreams, in Part 3.

Jennifer Alvey is a recovering lawyer who coaches unhappy lawyers on connecting with their happy, in work and life. Find out what that’s like by scheduling a discounted sample coaching session. It’s an hour that could change your life! Email to schedule yours today.


  1. You nailed it when you said,

    “When you’re young, everything feels new and exciting. You probably didn’t have enough experience to tell the difference between that kind of ooh-shiny excitement and the excitement that fuels your soul.”

    This ooh-shiny excitement is compounded if you grew up in a poor community where other kids in your high school were to a large extent either unmotivated or preoccupied with realities outside of school. To go from that to an environment where people (at least the ones in class) are engaged in the learning process creates this skewed perspective where each course/major seem rife with possibilities. It makes it impossible to discern whether you’re just getting caught up in the energy of other people, along with your own curiosity, or if you’re really doing something that speaks to your purpose.

    Of course it becomes quite apparent for many during law school (for me, by second year of law school) that the material is just not very interesting to them. But by that point you’re caught up in the inertia of it all and still hoping that the actual practice of law, since it’s supposedly so different from law school, will be a better fit. And, by the way, your summer internship was AWESOME.

    Then once you’re a practicing lawyer, you realize that law school by comparison was pretty interesting and depression slowly starts to sink in.

    • Yeah, summer associate gigs are the ultimate in ooh-shiny for us hicks from the sticks types, huh? At least, for me, eating at places with linen tablecloths all the time, and going to parties on a private island, were totally ooh-shiny. Plus it was fun to learn about the inner workings of store displays, or how designer clothes were marketed, etc. Even manufactured gas plants were kind of interesting to learn about, especially the memos when the cows drank from the creek by the plant and died shortly thereafter. But that was one document in 10,000. As we all know!

      • I am enjoying this blog very much. I spent many years as a prosecuting attorney. I am grateful that there were no billable hours to contend with but much of what you post translates to my experience. I was able to find new work but I do feel that alot my time was wasted. I regret that I didn’t accept that I didn’t want to be an attorney much sooner. I felt very obligated to stay in it becuase of the years and money invested in law school.

        I would also recommend a blog called I wish everyone good luck in find rewarding nonlegal work.

  2. Guest is right on the mark, as are you, about the excitement of the shiny and new. For most that lasts at least into a year or so of practice. After that, most of what you are exposed to looses its luster, if it doesn’t become actually distressing.

    I think this entry is very correct in its analysis. I also think there’s a couple of other factors to why so many lawyers end up discontented. One of those is that the study of law is particularly appealing to people with wondering minds. I think that very few lawyers actually have any real interest in the law itself. When studying law, however, they’re exposed to a lot of different topics and that’s what’s interesting. In actual practice, however, that is no longer the case as most legal work is actually amazingly narrow in its focus.

    Another aspect of it is that it’s a field that people with wondering minds are sort of pushed into. Well meaning friends, parents, guidance counselors, and the like see that a person has an analytical mind and they believe that this is well suited for a legal career, not being lawyers themselves. Being combative and liking to fight is actually a better personality trait for lawyers (in some fields) than being an analytical polymath. In the worst instance, the person in a legal career actually spends a lot of time avoiding his actual distasteful work, which is all fighting, and pondering everything else. In a high percentage of cases, however, the lawyer just dreads his actual work, which is all fighting and simply endures it, wishing he’d done something else. Part of the reason that its hard to get out is that the analytical polymath still doesn’t have any particular focus, so it’s hard to know where to go to.

    Finally, law schools perpetrate a false idea of the law on their students. Many law professors are refugees from actual law, and should know better. Next to none of them will go in and tell a group of new law students that unless they’re actually really interested in the law, not the stories, but the law, like to fight, and care about fighting more than love or money, they’re in the wrong place.

    • OMG, Brilliant comment! Yes – to non-lawyers, “smart” looks like lawyer material. To anything touching on litigation, “combative” is actually a better trait.

      And through all of this the polymath remains unfocused – also so true for so many. This explains my friend in a technical government law job who fantasizes about a fine woodworking and furniture business. His polymath intelligence still hasn’t been focused beyond (i) what I have to do and (ii) what looks fun right now. Hey, focus on a woodworking business launch – at least that is something more concrete.

    • Great point about the combativeness! And just to make it harder to figure out, I think sometimes people who look combative aren’t actually ones who enjoy arguing for the sake of arguing. They are idealists who are passionate about something, and will argue tirelessly, but only for a narrow set of ideals they really believe in. Arguing about the statute of limitations usually doesn’t fall into that set of ideals. ;P

    • ” In the worst instance, the person in a legal career actually spends a lot of time avoiding his actual distasteful work, which is all fighting, and pondering everything else.”

      I spent a lot of time pondering the stock market, the global economy, and secular cycles (such as the war cycle). I am still irritated that I lost money during QE II. Fortunately (or perhaps not), I went long in the beginning of February once I got a “buy signal” off the monthly.

      At least my mother in law now believes me that there was, in fact, a housing bubble.

      My wife refuses to let me get a Harvard MBA (because she’s still annoyed at the fact that I ran up that $120K tab at Duke). I should have gone ahead and gotten the MBA when I was at Duke.

  3. Very interesting piece! I also appreciate the comments by Guest and Yeoman, particularly this, from the latter
    “Being combative and liking to fight is actually a better personality trait for lawyers (in some fields) than being an analytical polymath.”
    So true! I don’t, really don’t like to fight. But I get a buzz out of analysing things, learning new things, finding out, understanding the lie of the land, the faultlines, the hills and valleys… Sometimes. I don’t want to do it all the time! Sometimes, I’d just like to design a book jacket, or organise a TEDX conference!

    It’s hard to separate oneself from the law – to really know if it’s just me, is there something better, did I make a mistake, was it the best decision in the circumstances but should it be revisited, and so on…. All the questions you consider on this blog.

    Thanks – thought-provoking as always.

    • Jenny, if you haven’t taken a Myers-Briggs evaluation, you might get a lot out of it. Most lawyers who like being lawyers are “T”–they enjoy thinking dispassionately about problems, rather than relying first on values to analyze a problem. And T’s usually enjoy arguments–they are fun mental exercises, rather than expressions of disharmony that Fs feel arguments are. (F is on the opposite end of the preference scale from T). If you look up my posts on The Lawyer Personality, especially on the T/F dichotomy,, you can get the background there.

  4. Creativity is so very important. It’s an emotional and mental outlet that nothing else can provide. I used to write poetry and draw and make all kinds of art projects as a kid. After law school I didn’t partake in any creative activity at all for years, and I felt my soul kind of dry up and deaden. I never felt the kind of happiness that creativity brought me in my younger years. And I even felt like I didn’t know how to get back to that creative place in my heart and mind anymore. But I had to try! And I think I succeeded. I spent a year being a featured photographer in an art gallery, I started my blog, and I am working on a book. And now I feel like this is what I should have been doing all along, instead of what I had been doing. Now I am looking for a permanent way out of the daily office grind, and when I find it, I will never look back!

    • I loved law school. It was the first time I was really challenged. It was difficult. There was this vast universe of knowledge I needed to consume and absorb, and I loved every minute of it.

      The irony is that some of the best law students make the worst lawyers. Being good at issue-spotting and making judgments as to likely outcomes/risks based on existing case law is one thing; being comfortable arguing positions you know are unlikely to prevail is quite another. I have found that most “book-smart” attorneys, like myself, are actually horrible litigators. The best litigators are the B-C students who will argue until they are blue in the face even though they do not really comprehend the substantive law they are arguing.

      Analyzing issues with logic and cool detachment is not what persuades juries or judges. I am always amazed how all the senior litigators think depositions are “fun.” I have no interest in having a measuring contest with opposing counsel over what side of the street a deposition is to occur, who gets to sit on what side of the table, and whether someone can object to my objection to their objection to a legitimate question. Also, I find there is something inherently wrong when on a daily basis I am required to “make a non-frivolous argument” with zeal–i.e. argue a position I don’t believe in and that I know I won’t win.

      The other irony is that the people who are actually good law students, who can analyze and parse complex issues and apply convoluted precedent to a new set of facts would make the best judges, but will never be judges because only successful litigators become judges.

What's your take?

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.