Chasing the Perfect Job, Ruining Your Alternative Legal Career Search

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As I’ve written about several times (here, here, and here, for starters), perfectionism is an especially strong demon for most lawyers in their alternative legal career search. It’s one of the six attitudes that hold lawyers back in their search for a better career and life, and it’s got such a powerful hold over most lawyers that it gets its very own post.

Not following the perfect path, the pattern set by others, can lead to something fun and better.

The nub of perfectionism is worrying others will discover you are not enough, and gearing your actions and focus to eradicate that feeling of being less than perfect. The focus on the extrinsic—the partners will look down on me if I keep driving my dinged-up, paid-for Toyota, better get a BMW—keeps you from connecting with your authentic self. It’s all about external validation. Perfectionism walls you off from your own, fantastic inner wisdom, because it substitutes others’ judgments for yours. It keeps you conforming to others’ limitations, rather than exploring your own unique gifts.

Here’s a tip: No one is perfect. We all have flaws, some of them deep and juicy. Our flaws are what make us interesting and human. Lots of people think that if they were perfect, every single one of their problems would disappear. It’s more likely they would become insanely boring and horribly insufferable. And, they still wouldn’t be happy, because they’ve stopped listening to their soul.

Excellent, not Perfect

I’m not saying to avoid striving for excellence. That’s no fun at all, to settle for the mediocre if you can do better. But excellence and perfection are quite different.

Excellence is about doing the best you can, but accepting that there is no such thing as flawless. It’s about being curious, about seeing how close you can actually get to flawless, and not beating yourself or your team to an emotional pulp if you fall short.

Perfection comes from a completely different motivation—trying to hide, to cover up feelings of inadequacy. It is the siren song of “not enough.” If you don’t achieve perfection, you feel like a failure. It’s the person who wallpapers a kitchen, with all its angles and weird dimensions, and bemoans how dreadfully it turned out because 2 of the 23 pieces were 1/16” off.

The Perfect Job Chase

In a job search context, you miss a lot of great opportunities when you insist on the perfect job to get you out of law. It has to

  • pay enough to keep your kids in private school and you in your 4,500 sq. ft. house in that really nice neighborhood,
  • have no less-than-scintillating aspects to it,
  • have completely, wonderfully nice people, no exceptions,
  • with an office that has a door and a window,
  • in the fashionable section of town you like, and
  • have a very clear, predictable path to promotion and success that you don’t have to create.

Otherwise, you’re just going to stay in your high-paying, depression-inducing, soul-killing law job.

Yes, it sounds ridiculous, but I assure you I talk to people every week that harbor that attitude, even if they won’t articulate it so bluntly to themselves, let alone to me.

Instead of a perfect job, aim for an interesting one. Look for the intriguing or challenging. The uncertain but exciting. Don’t look for a total match with what you’ve already done–you’re trying to escape that. Innovate your new career, instead of merely changing the office where you’re miserable and deeply unsatisfied with your work. Take a less than perfect step, and see where it leads.

And if you haven’t read it, pick up a copy of Brene Brown’s The Gifts of Imperfection. And watch her TED video.

Next time, I’ll cover a couple more crippling attitudes lawyers carry around: avoiding discomfort and risk, and using productivity as validation.

Jennifer Alvey is a recovering lawyer who coaches unhappy attorneys on disarming their inner perfectionist so they can get on with their career search and a more fulfilled life. She offers discounted sample coaching sessions. Schedule yours today by emailing


  1. Great post!

    Being open to new opportunities and new challenges is so important when looking for an alternative legal career. I found it really helpful to put pen to paper and actually write down the top 3 priorities I was looking for in an alternative legal career. It helped me to stay focused and not get too caught up looking for perfection.

  2. You know what’s not perfect? This username. Somebody always takes JP, but JonLaw?

    How many people out there want to riff on John Law? Most people have zero interest in economics, let alone John Law.

    So, I’m JonLaw2. Great, just great.

  3. Yet another great post 🙂

    One of the BIGGEST hurdles I had to overcome with my job search was understanding that it would very likely require me to have to take a significant step backwards as far as my earnings. I also had to understand that there were going to be days in my new career when I would just want to throw up my hands and scream “UGH!!! WHY!?!?!??!”

    Yes, I did take a ginormous step back in salary. Yes, I do have days where I’m frustrated to HECK. But am I a HECK of a lot happier with life? Absolutely. The only things I miss about Big Law are the big paychecks and some of the really wonderful people I met while working at my old firm. But both of those either have been remedied or will be remedied. I stay in touch with all my old friends, and I know that with time, hard work and faith, I will be making a very great income in my new chosen profession (NYC real estate agent).

  4. Let me pose my odd query here.

    I generally agree with this post, and probably with most of what’s posted here. And I do want out of the legal field. So what’s holding me back?

    I guess my big problem is that what I really want to do is to be a farmer, full time. Not a hobby farmer. It’s what I’ve always wanted to do, but I haven’t managed to make it happen. And I can’t seem to get any support from anyone on it. My family doesn’t take it seriously, and my in-laws, who are in agriculture, are so convinced that my life must be glamorous that can’t even conceive of the desire to move from my job to theirs. It’s hard to figure out where to turn.

    And, to add to it, where I am, unless you are born into it, getting into agriculture is really expensive. I don’t even know, at this point, how to really get started. After 20 years of being a litigator, I’m afraid I never will.

    What should I do?

    1. You are the stuckest poster I’ve seen around these here parts. By that I mean, you want to be a farmer, don’t want to be a litigator, and you keep talking about it. I seem to recall that you’re in Kansas or the Rockies or something, which means that you are actually around actual farmland.

      First, you need to move beyond the talking phase into the actual planning phase. Meaning figure out how to get from point A to point B.

      1. Right again. That’s actually, oddly enough, one of the hardest things to get information on if you are from the outside. When you start to dig, no matter who you ask, and you say “let’s discuss the bottom line of this operation” they hear “I’m a lawyer and that’s super glamorous. . . let me tell you about my representation of the Khardashians. . .” or something.

    2. When people have an alternative they really want to pursue, but aren’t, it can be a sign of being afraid of success. Oddly, this is a manifestation of perfectionism. If you succeed, it might not be exactly the way you envision it, in fact it might be downright unpredictable and uncontrollable, and then you won’t know what to do–because you lack the perfect plan. Of course, that may not be your issue at all, Yeoman. Just tossing it out to consider.

      So if people don’t want to discuss their bottom line, maybe you’re asking the wrong questions. I wonder if you might get further if you ask them, what would your advice to someone like me be–someone who wants to do this but doesn’t have the equipment, machinery, etc.? Or, would you advise anyone to go into farming right now? If not, why not?

      Good luck!

      1. Thanks. Very insightful comments. I suspect that you’re right all the way around.

        Part of the problem too is that I have real opposition to this plan at home. I spent part of the day today making contacts on ground to lease and, wanting to be open on moving along, noted that in part of the “what did you do today” discussion at home. Predictably, my wife was terrified. It isn’t as if we’re rich by any means, so while our income will be really dropping, it isn’t as big of drop as it might seem, but anyhow, pursuing things with no support is the pits.

    3. I understand why you dislike commercial litigation.

      However, why do you like the idea of farming? And are we talking cow farming (milk), crop farming, or some sort of New Age organic happy vibration farming?

  5. I’m talking livestock (beef cattle) but I like all types of farming that I’m familiar with. I’m not familiar with dairy production, however. Anyhow, I’m basically talking ranching, but I’m familiar with row crop and I like that also.

    As for why, that’s hard to say. Why a person likes what they like is almost more difficult to define than why they dislike what they dislike. At the end of the day, what I guess I’d say is that I like working with animals and I like being outdoors. Also, most agriculture is a relatively isolated type of work, where you aren’t usually working with very many people, if anyone, or only work with large numbers of people on occasion, and I like that. Indeed whole days will go by when you don’t really work within anyone other than yourself.

    And the goals are just different and visible. You know very clearly if you achieved them or not, and why you are trying to achieve them. You’re working with nature, and at its mercy, and that’s very direct. Everything you are working on resolves seasonally, and that’s nice too.

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