The Problem Hunter and the Dream Career Search

As I’ve posted about previously, law is one of the few professions where being a pessimist actually makes you better at your job. Lawyers are trained to look for the downsides and figure out ways to protect against them.

lion hunting wildebeasts

If the obstacles to your dream job are as numerous as wildebeasts, you may be a world-class problem hunter.

But what makes you a good lawyer—being a problem-hunter—generally makes you terrible at living your life happily. That is particularly true when it comes to thinking about an alternative legal career search.

Usually the first thing alternative legal career seekers do is problem-hunt. As in, “Well, I’d like to [fill in blank], but I don’t think I have the skills/experience/right clothes. And getting those skills/experience/right clothes would take time/money/focus I don’t have.”

See all those problems? Yikes, no wonder it’s so hard to get out of law. There’s a Mt. Everest of problems to scale before you can make a break for it. At least, if you go into problem-hunting mode.

What I find interesting is how lawyers can problem-solve so well in many areas, but when it comes to things they are fearful about, they switch immediately into problem-hunting mode. For instance, I know a partner at a BigLaw firm who has an outstanding track record in solving the myriad of problems that come up in multinational litigation. Yet when he considers leaving his current firm for an environment better suited to him, he starts problem-hunting on a grand scale. “Well, if the firm finds out I’ve talked to any headhunters, they’ll fire me.” Right, because no one in the history of the firm has ever looked at their options elsewhere.  Or if they did, they were fired on the spot. Yeah.

When you’re in problem-hunting mode, you’re basically gathering evidence against doing anything. Seek, and you will find all the reasons you need for not taking the path you’re considering. It’s a proven way to block forward movement.

Am I saying that you should ignore all your fears? Of course not. Sometimes our lizard brains are right, and there is a real, honest-to-goodness threat to your contemplated course of action. Thing is, lizard brains are like broken clocks—they’re bound to be right a couple times daily. But their accuracy ain’t so hot the rest of the time.

So how do you tell what fears to take seriously? It helps if you’re connected and really tuned into your inner truth. That’s the part of you that knows what your best path is.

One way to get in touch with that inner truth is to use a Martha Beck technique from her book Steering by Starlight: When faced with a decision about what career path (for example) to pursue, ask yourself whether doing it feels like freedom.

Note that you don’t ask yourself what is less scary or more likely to succeed, or feels safe or feels like relief from the horrors of your current job. The kind of freedom I’m talking about is what makes your inner self, your soul, feel like it’s soaring.

When you’re pursuing what feels like freedom, problems once again become a puzzle to solve, rather than an insurmountable set of obstacles. That’s the kind of truth that will set you and your career free.

Jennifer Alvey is a recovering pessimist and lawyer who helps attorneys become great problem-solvers of their career dilemmas. What’s your problem you need to solve? Contact her at jalvey AT

2 thoughts on “The Problem Hunter and the Dream Career Search

  1. Pingback: The Dilbert Principle for Lawyers « Leaving the Law

  2. Pingback: A Lizard Brain Attack « Leaving the Law

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