So here we are on the threshold of a new year, when everyone gets their panties in a twist about changing their lives for the better. Now, don’t get me wrong, all you unhappy lawyers, I am a big advocate of change that makes your lives happier and more fulfilling. It’s just that most people go about it bass-ackwards.

Disappearing Cheshire Cat
Are your dreams weird enough?

“I need a new job! Then my life will be better.” Yes, there’s a lot of truth to that, particularly if you work in the highly toxic, PTSD-inducing environment that is most law firms. In your desperation to escape—and I don’t blame you—you’ll take a lot of jobs that, in hindsight, you may just smack your forehead and say “My God! What have I done? This is not my beautiful job! This is not my beautiful life!”

You know what? It’s OK. Because no one said, except maybe an inner critic’s voice in your head, that you had to make your escape from law in one perfect, Hollywood moment of a move. Many times, you need to take that slightly-less-shitty job to learn some stuff. It can be job skills, or how non-lawyers operate businesses, or even stuff about yourself.

The key is to simply take a step in the right direction.

But what if you aren’t sure what direction that is? That’s where dreaming comes in.

More Than Pretty Pictures

I’m not talking about nice, safe career dreams you can discuss with relatives or other cranky people in your life. I’m talking about the kind of dreams you have at night, the ones that are a non-sensical jumble. The ones that leave you with a sense of longing, wonder, and a whiff of fear and confusion.

For example, when I was plotting how the hell I could leave law, I kept trying to articulate that I wanted to do something visual. Something with images. But how on earth could I even think to do that? I had zero training in graphics. (This was the late 1990s, remember, before you could learn everything on YouTube or Pinterest.) I had nearly zero experience in visuals, unless you counted fiddling with all the font colors in Word, and a little work I had done on supervising photographing of exhibits for summary judgment. So I dismissed that thought as irrelevant.

Fast-forward 5 years, and I was the editor-in-chief of a magazine. Yep, a magazine, with tons of art elements accompanying stories. Despite myself, I had managed to find that job with visuals. To this day, it remains one of the best jobs I’ve had.

So let yourself dream those crazy dreams, even though they don’t make sense. Access them through a vision board, or just visualizing your ideal house, office, or even the clothes you want in your closet in 5 years. Go for walks, or visit new and different stores, and see what speaks to you. Just because you love looking in a bakery window doesn’t mean your secret inner desire is to be a baker; often these longings are less direct than that.

Your job is to pay attention, make notes, and be open to dreaming. The more you are open to that, the sooner your dreams will start to emerge.

Here’s to your year of dreaming.

Chalk Drawing - If Your Dreas Don't Scare You they Aren't Big En
Are you scared yet? I hope so!

Jennifer Alvey is a recovering lawyer whose visions are usually far more challenging than sugar-plums. She’s learning to be OK with that. If you want to talk to her about your crazy, but-what-if-I-could kind of dreams, email her at to set up a sample session.