What If I Regret Leaving The Law?

It’s one of the most common questions that I hear from unhappy lawyers: what if I regret leaving the law?

And I totally get it. I asked that question myself. To step from something known (even if you’re miserable) to something completely unknown is legitimately scary.

So let’s talk about what you need to know if you’re worried that you’ll regret leaving law.

Would you rather watch than read? Click here to watch Sarah answer the question, “What if I regret leaving the law?”

Do you ACTUALLY think that you will regret leaving the law?

If you’re asking yourself, “What if I regret leaving the law?”, here’s the first thing I want you to think about… are you ACTUALLY worried that you’ll regret it?


So often as lawyers we feel like we need to protect ourselves by thinking about the “worst case scenarios” that could result from our decisions.

Before you do anything else, genuinely ask yourself–do I actually think it’s likely that I will regret leaving the law?

Are you really worried about what people will think?

Second, I want you to recognize how much your concern that you’ll regret leaving law is actually concern about other people thinking that you made a bad decision. And most of the time, those are people that you don’t even like!

As lawyers, we tend to believe that there is some objective, one-size-fits all metric that provides a single optimal answer to every question. It feels safe to believe that there is only one right answer to the question of what we should be doing career-wise.

I’m not saying it’s easy to let go of the fear of what other people will think. But you really want to make sure that when you’re wondering whether you’ll regret leaving law, your real concern isn’t other people thinking you SHOULD regret leaving law.

Even if you regret it, so what?

Third, let’s imagine that you decide to leave the law, and then you genuinely regret it.

I can’t even name someone for whom that’s true, but let’s imagine it anyway.

So what?

Seriously, so what?

While we are wired to avoid negative emotions like regret, trying to avoid regret is a losing battle. If you don’t leave the law because you fear regretting it, ultimately you’re signing up for a different type of regret—regret that you stayed and felt stuck.

And you’re already experiencing negative emotions about your career now. So the real question you need to ask yourself is what type of negative emotion are you willing to tolerate.

You can change your mind

And more importantly, if you leave the law and regret it, you’re not stuck. You changed your mind, and you can change it again. You will have options, and you can do other things—even return to practicing law, if that’s what you decide is best for you.

To be honest, often “what if I regret it” is a mask for a bigger concern, which is “I have no idea what I would do if I left.” It can be completely bewildering to realize that you are years and even decades into your career and don’t actually know what you like or what you want to be doing, other than “not this”.

Answering the question, “What do I actually want to do?”, when you truly have no idea, can be extremely daunting. It makes it more likely that you will focus on other questions, like the question of whether you will regret it.

If that’s you, download my free guide, First Steps To Leaving The Law, or join my program for lawyers who want to identify alternative careers.