How I Actually Left the Law (And What No One Tells You About Switching Careers)

Nov 29

Some people might say I’ve had a less-than-traditional career.

Fair enough.

On the surface, it looks pretty straightforward — I went to law school, became a lawyer, ran a practice.

But I’ve also simultaneously and sometimes concurrently done a lot of other things. Ran a film festival. Photographed professionally. Produced film. Left law. Started a coaching and advisory business.

And so, in that regard, the path itself has been anything but traditional.

Because of that, I get a lot of questions.

Earlier in my life, people asked, “How did you become an entertainment lawyer? How did you build that business and practice?” When I was more active as an artist, the question was, “How do you do that and also be a lawyer?” And once I left law, it shifted into, “How did you get out? How did you actually make that leap?”

These conversations go a lot of different ways, so I figured it might be helpful to lay out a few of the questions I get most often - and the answers I usually give.

I am often asked how I’ve ended up doing what I do - so, here are my most frequently given answers. Share with those you know who might be asking the same questions!

1. “How did you do it?”

This is the first big one. And, I think, it really hides a number of other questions. But, people like nice, packaged questions to go with nice, packaged answers.

The honest answer is: I don’t really know. I’ve had a lot of help. I worked with a great therapist for a long time. I worked with coaches. And, to be blunt, I suffered a lot.

But in the suffering lies the teaching.

So much of the process was revisiting what mattered to me - again and again - and asking myself what I was actually willing to do in service of those things.

As a lawyer, building a practice, I asked, “Who do I want to work with? What types of problems are the most interesting to me? Where will I be able to, most likely, marry my interests with the profession I was trained in - and make a living doing it?”

As an artist, it was largely the same questions - “What story do I want to tell about myself and my work? What feels like an honest expression of my feelings on the world and the work I am doing?”

Even now, whether I am entertaining producing a project, developing a workshop, or assessing whether to work with a person or firm, the questions often feel the same: “Is there alignment between what matters to me and this person/team/company? Are the challenges that are presenting in this case areas of life that I am not only interested in, but also, am able to be of service to? Do I feel something when I am considering this person/project?”

Of course, the answers to these questions are not fixed - much as the questions are not fixed themselves. They changed as I grew, as my practice evolved, as life changed.

The biggest shift was, of course, when I decided to leave law. I had struggled for a long time with “being” a lawyer (I use “being” in quotes intentionally - because it’s partially a way of being, but also, a job - it just sounds weird to say I’m “doing” law. But, that is a topic for another day.) Because, at that point, what mattered for me had changed.

It didn’t feel like me - it hadn’t for a very long time. I’m not sure it ever did. And I still struggle with that question — what is really “me”? I’m not entirely sure. And, might not ever be. But, this feels like it’s getting closer.

Which brings me to the nut of this whole “How did you do it?” question - I finally began the process of letting go of the fight with myself.

2. The Practical Side: Conversations and Curiosity

On the practical front, I spoke to a lot of people. A lot of people. That’s usually the advice I give to anyone starting a legal practice (or any business, frankly): network your face off. Do it without a specific target in mind. I didn’t know what my legal career was supposed to look like. I vaguely knew I wanted to be near the arts. Entertainment law sounded like the obvious bridge. But I had zero expectation it would actually happen.

So I talked. I asked people a lot of the same questions I am highlighting in this article:

What’s it like? What do you actually do? How would I even get into this? Who else should I talk to?

Networking turned out to be a real skill for me — one I enjoy and one I teach now. And exploration became the backbone of every transition I’ve ever made. It required being open, curious, and, frankly, willing to tolerate a lot of uncertainty. That part was uncomfortable. Painful, even. But that discomfort was the price of admission.

And, it continues to be - in every facet of work that I do. Most notably, it is also the most important part of getting out - of a career, a job, a relationship. Talking about it is not enough on its own, but it leads to clarity. Be selective about the inputs, of course - we have the power to make decisions for ourselves, after all - and we are accountable only truly to a very small list of people.

But, the “What’s it like?” conversation is just as powerful for the exit as the entrance (and reminds us, like William Bridges, that changes really happen on a continuum and are not simply distinct events). It gives us the sense that, while we may not really know what it’s like until we are doing it - until we are “there” - it at least lets us prepare on some mental, emotional or psychological level - and, to strategize.

3. Leaving Law Was Scarier Than Entering It

If getting into law required courage, getting out required more. I had to trust — in the Ray Bradbury idea — that if I jumped, I’d grow wings on the way down. I didn’t fully believe that.

In fact, it took the repetition to me by a number of people I trusted that, yes - it would be OK. But, would it?

This is where I think the hardest part of the process comes in. Faith. Hope. The belief that, yes, this is really hard and you are saying goodbye to a whole “thing” that you’ve built up (and everything that comes with that), and it’s going to hurt and be a loss which, at least on some level, you will need to mourn and grieve for some as yet indeterminate period of time.

But, on the other side of that period is a time and place where things will improve and will be better than where you’re at now.

Perfect? Of course not. Guaranteed success? It would foolish to believe that.

But, different? Shifted? Perhaps, maybe, better?

Yes, absolutely. If you’re an optimist.

It’s true that your faith - your ability to hope - will continually be tested. But, learning to be an optimist - learning to trust not only in the process but also that it’s OK to hope and be disappointed - are crucial.

4. “Did you know what you wanted to do next?”

Now, it’s one thing if you know what you’re aiming for when you decide to make the switch. I think that could make it a bit easier because, if you know the destination, you can at least start to assemble a path there. It may not be the final path, or the perfect path - but the first steps are visible.

But, when you don’t know? When you really have no idea? That’s a different challenge. And one that, I am learning, is so much more common that most of us are led to believe.

When I decided to leave practice, the only things I knew were:

I needed something more creative.
I wanted to keep working closely with people.
I didn’t want to live in a high-liability profession anymore.
I needed more flexibility — more life, less being on-demand 24/7.
I didn’t want to “sleep with my work,” which was basically how I operated as a lawyer.

There are lots of jobs that could have given me some or all of those things. Sometimes I still think about those. But this kind of coaching/consulting/advisory work ended up being the right combination of ingredients.

For now.

And, yes, that is an important one to flag.

I think many of us approach our next phase of work or career as, “Well, this time, this is going to be it. I’ve finally figured it out.”

But, did you think that when you chose the first profession?

If so, then perhaps you were wrong? And perhaps you could look at this shift as temporary as well?

Because, in all likelihood, it will be.

Accepting that actually makes it easier to make the move. If it’s not final - if it’s not the “be-all, end-all” - then it takes so much pressure off the choice - because it can be undone.

It’s one thing to consider your identity as relatively permanent. You sometimes see this with artists - at their soul level, they are artists - regardless of whether they paint or draw or make a living as artists.

But it’s another to think your work is unchanging. And I don’t mean your work in life - your mission, calling, vocation. I think that probably stays pretty consistent.

Which kept me coming back to this question of, “Who am I, really?” I’ve always been the kind of person people open up to, unprompted. I’ve been told I’m disarming. Someone recently told me, “That’s a gift — use it.” That was true in law, and it’s still true now.

So the work became less about following some prescribed “should,” and more about using what I’m actually good at or have a gift for - listening, connecting, helping people make sense of their inner worlds.

5. “How did you build the business?”

I don’t have a clean answer to this (which, by this point, should not surprise you). Everyone builds differently.

I think the trick — if there is one — is to lean into your gifts. If you love networking, do that. If you enjoy speaking into a camera, do that. If you like writing, lean on writing.

For me, in all the work and jobs I’ve done, it was talking with people. Getting a million lunches and coffees. Joining

For you, that might be something different. And if you don’t know what that is, ask less “What am I good at?” and more “What is fun?”

Marketing and business development have to be fun or you simply won’t do it.

For instance, if you hate cocktail parties - the classic networking scenario - then don’t go. Unless you can learn to like them and enjoy them and feel natural in them - don’t use them as your method of business development and building the business.

And when it’s fun, you also show up more naturally. More relatable. And people fundamentally want to work with someone they can relate to — whether that’s a coach, a therapist, a lawyer, an accountant, whatever.

6. “Why make the changes?”

To put it simply: there’s only so long you can deny yourself.

I could tell a longer story about the exact moment or the circumstances around leaving law, but the real answer is already buried in everything above: something was itching for so long that I just had to scratch it and I couldn’t any longer pretend it wasn’t there anymore.

Which leads me to the question I would invite you to consider (if you’ve read this far): What have you been denying yourself? If you have a feeling, a thought, an ominous sense that you’ve been rejecting a call to do something that, for some reason, seems to just “work better” for you - then at least look at it. You don’t need to make any drastic changes - you don’t need to burn it all down (take it from me, that way is much harder). But, you owe it to yourself to really wrestle with the question and get some clarity on the answers.