An Open Letter to the Successful But Unhappy Lawyer - Legally Bold

Are You Over It? An Open Letter to the Successful But Unhappy Lawyer

Are You Over It? An Open Letter to the Successful But Unhappy Lawyer


Where do you go when you have everything and nothing at the same time?

Dear Successful But Unhappy Lawyer,

First, it’s an honor to be writing to you. Whether you believe it or not, you’re a big deal, and I’m not just blowin’ smoke.   You are a leader. In school, you were always the head of any group project, course, or organization because you care about people.  You wanted to help and make things better.

Your desire to help carries over into your life as a legal professional too.  Your dream is to be a legal superhero. This means slaying your client’s dragons, making it rain in your firm, and hobnobbing with the best and brightest.  This may sound pretentious, but that’s not the case at all. You are humble, curious, and likable, and those traits tend to attract the best things in life.

The problem is that you’re not exactly sure that you want to be a lawyer anymore.

In college, you were good at pretty much everything.  You did the work, read the assignments, turned in the papers, and got the grades.  But by your junior year, you still weren’t sure what you wanted to do with your life. Sure, you declared a major, but all you really knew was that you wanted to make lots of money and enjoy the good life.  Law school seemed like the fastest and safest route to that goal. Plus lawyers enforced child labor laws, wrote civil rights legislation, and put criminals behind bars. It’s a noble profession, and one you can be proud of.  So you applied.

By your 30s, you were reaping the benefits of your law school decision and years of hard work. You graduated from law school and joined a firm. On the personal side, you’re in a committed relationship, find time to work out, pay your mortgage, take cool vacations, and eat clean. Basically you are the picture of success and achievement. You should be happy. You should feel amazing except that every morning when you wake up, you are crying in the shower. 

Enter the unhappy lawyer.

Despite your best efforts, you never feel confident or comfortable at the firm.  At work, you stay in a constant state of anxiety hoping that you won’t be called out for making some unknown mistake.  Although you are the firm’s go-to person in your practice area, you hate it the area, but you’re too afraid to speak up about it for fear that you won’t get the work you need to meet your billables.  You can’t remember the last time you were able to relax. Instead, every day is like navigating a minefield as you try to please partners, respond to clients, and keeping adversaries at bay. This is all too true of solo practice lawyers as well. 

You know this isn’t the life you want, but you don’t know what to do next or how you can afford to pay your student loans while you figure it out. Where do you go when you have everything and nothing at the same time?

You go within.

I know this sounds corny, and you’re not into this new age, self-awareness stuff. But humor me for a second. There are a few truths that you know about yourself deep down in the self-awareness part of you.

You know that you’ve always been willing to do what it takes to get where you want to go. You finish what you start and get to that finish line no matter what. You also know how to navigate to a destination once you decide where you want to go.  That’s what lawyers do. We create a plan to get our client a particular outcome. These are remarkable traits that you can use for your next career. The only question that remains is how do you find that next career.

The answer is wayfinding.

Wayfinding is the process of moving toward a destination in your life when you are not really sure where you want to go. To wayfind, you try on new career identities to see what fits and determine if these new identities work for your current life. This is not a time to be practical.  It is a time to go for what you want and try on everything no matter what it is.

So how do you go about wayfinding without going broke or curling up into a ball in the corner? Give yourself permission to dream. Take baby steps.

You keep your current job with the intention of wayfinding. Then you figure out ways to try on other career identities that feel more in line with who you are. Can you interview some who has the role you want and figure out how to get there?  Can you take a few days off to write and submit that sitcom script you’ve been dreaming of? Here are a few more ideas to get the wayfinding process started.

Take A Class 

If you have an idea for a business, a book, or a creative endeavor of some kind, take a class related to a skill you will need in that line of work. You’re a lawyer, so you probably like to learn and taking a class will make you feel more confident that you have the chops to pull off what you set out to do.

Build Your Community

While your in that class, start chatting it up with your classmates, teachers, and guest lecturers about your next career move.  Often those connections can help you find the resources you need to move to the next step on your wayfinding mission. You can also find mentors, friends, and inspiration from like-minded people who are taking leaps of their own.  They know the ups, downs, fears, and triumphs and are better equipt to support you when things get rough.

However, avoid discussing your plans with anyone who does not support your dreams. They do not understand your desire for something more and talking with them will only confirm the fears that you already have in your head.  Your inner critic is providing you with more than enough doubt. You don’t need any other outside sources.

Change Your Routine 

When I was the traditional unhappy lawyer working my 9 to 5, I unintentionally ended up doing everything the same way every morning.  It was my routine. I woke up at the same time. I got up had breakfast, showered, brushed my teeth and got dressed in the same order.  I even took the same route to work every day. While great habits are important, they work best if you intentionally create them. If you find yourself performing an unintentional routine daily for the sole purpose of convenience, it can stagnate your creative and growth.  To get comfortable with taking risks and wayfinding, shake up your morning routine. Take a different route to work, have breakfast at a new diner, reversed the order in which you get dressed. These small steps will have a profound impact on your mindset. Trust me.

Feel the Fear and Do It Anyway

Will Smith once said that God puts the best stuff in life on the other side of fear, and every great experience in my life confirms just that. So use fear as a guidepost to let you know that you are heading in the right direction as you wayfind.  Fear is not the same as being unprepared or fearing that you will be caught for some unethical behavior. Fear, in this case, means getting outside your comfort zone and trying something new without any guarantees. Stick with it, and you’ll find the best stuff on the other side.

Are you ready to make changes in your career to leave the unhappy lawyer behind? What steps can you take now to help you get to your unknown destination? Let me know in the comment below. I’d love to hear your thoughts.