“I’ve invested so much in law, I feel like I can’t leave it.” This is the point at which I sometimes mentally smack my head and wish I got paid by the phrase. I would charge a lot for this one.

dollar falling from sky over businessman
If your investment in law doesn't make you feel this good, you might want to rethink whether it's worth keeping in your portfolio.

Um, really? So if you won $50 million in a lottery, you wouldn’t leave law? You’d show up the next day at the office and happily put up with all the stuff about law that drives you bonkers? Right, I didn’t think so. There are lawyers who would keep practicing law, but they don’t read this blog and fantasize about leaving law.

Let’s break down what the investment is, anyway. It’s time, money, and lost opportunity costs.

Time and Money Invested

Time is the easiest to get past for most. You can’t get time back, unless someone actually goes and invents a time machine. You are going to be a year older in 365 days whether you are a miserable lawyer, a recovering lawyer, or a lawyer/whatever. Clinging to a time investment doesn’t serve anyone well, because it’s just clinging to the past rather than embracing the future.

Money is harder for a lot of people. Law school loans can be daunting, particularly in a down economy. You might need to really adjust your standard of living for a while as you transition out of law. Because your current standard of living pays for a lot of distractions from your grinding misery, that can seem like a hellish option. It’s actually not as bad as you fear; $15 sandwiches don’t taste nearly so good as loving what you do for most of your days. Really.

Stuff weighs you down; lack of excess cash to buy lots of meaningless, distracting crap is freeing. I’m not just blowing sunshine up your skirt (or pants), I live it. When you don’t spend as much, you value what you do spend on much more. Valuing what you have—wow, there’s a concept.

The Life You Haven’t Had Time to Live

What really keeps most people mired in their so-called investment in law is their lost opportunity costs. Rather than learning how to

  • be innovative,
  • motivate a group,
  • help people,
  • save the world,
  • run a business you care about,
  • develop a product,
  • explore creativity, or
  • do any other thing that truly interests and excites you,

you’ve been learning all about scintillating things like the measure of damages for contract breach in California and Delaware. And how to survive in a seriously dysfunctional workplace. And how to help corporations play shell games. I seriously doubt most of you reading this actually care about the substance of the law you practice, let alone the other stuff.

What you do care about is being an expert, being accomplished, right? Having respect for your knowledge and hard work, maybe? Knowing that you have been baptized by the fire of law practice and are still breathing, perhaps? Never mind that some days, you feel like you’re barely existing.

You Are Enough, Right Now

Worrying about walking away from everything you’ve invested in law is really a worry that you aren’t enough. Because you know full well that, absent a lobotomy, if you leave law you will retain

  • your analytic skills,
  • your ability to process large quantities of information quickly and accurately,
  • your ability to marshal your thoughts logically,
  • your knowledge of how the business world works, and
  • your skill in parsing complex laws and regs much more easily than the average business or consumer bear.

In fact, you get to take all of that, and then go off and use these valuable business and life skills in new ways, combined with new knowledge, skills, and experience that you will be acquiring. Sounds cool to me.

Some Inspiration

Maybe the story of Gretchen Rubin will inspire you. Gretchen Rubin is someone who tossed her considerable investment in law aside. That investment included a Yale law degree, editing the Yale Law Journal, and a Supreme Court clerkship. I’m not sure how much more invested in law you could get than that.

During her clerkship, Rubin realized that she wasn’t interested in law, and that in fact, she wanted to be a writer—and that people had jobs with that title. So that’s what she did.

Her latest book is The Happiness Project: Or, Why I Spent a Year Trying to Sing in the Morning, Clean My Closets, Fight Right, Read Aristotle, and Generally Have More Fun. I haven’t read it yet, but it’s on my short list of books I need to read soon.


At the risk of putting on my Captain Obvious hat, try figuring out what you’re really scared of losing if you leave law. The feeling of being a survivor? Respect? Money? Approval (from family, friends or society)? And then, the part that shouldn’t be hard, but usually is: Is that worth having, at the cost of a life and work you dream about? Will that feeling or thing it make you wake up feeling like you’ve won the lottery?

Jennifer Alvey is a recovering lawyer who coaches unhappy attorneys on how to invest themselves so that they have a life and work that truly pays off for them. She offers discounted sample coaching sessions so you can see how coaching can help you find your right life investments. Email her at jalvey@jenniferalvey.com to schedule yours today.