Find Your Personality in Your Career

Leaving the Law is delighted to welcome Chelsea Callanan, founder of Happy Go Legal, as a guest blogger. Chelsea focuses on helping lawyers find the right fit for them in a legal career. More on that below.

During law school, we are all pressured to be part of a herd. No matter how unique you felt going into law school, no matter how righteous your specific reason for wanting a JD, you likely didn’t make it through the three grueling years without adopting at least some of the herd mentality. Dreams of working at a non-profit environmental organization are quickly shelved as everyone begins competing for the few jobs at big firms. Even if it does not feel like a good fit for you, it is easy to want to compete to “win.”

herd of wildebeast crossing river
Sure there’s safety in numbers, but the crocodiles can still get you if you choose poorly.

Because of this herd mentality, many new graduates end up in jobs that are a horrible fit for them. They “won”––but in fact may lose years of their lives, lose respect for themselves, or even lose themselves in the job––because of one rash decision. Even if you skirted the herd, and stuck to your guns about finding a job that was a good fit for you, you may now be questioning how well you knew yourself or what you wanted. So in an industry where there are more lawyers than traditional jobs, how do you find your personality in your career?

I talk a lot about helping lawyers find success and sustainability in their legal careers. If you are feeling burned out, or are feeling like you are being stifled or held back in your current job, this can of course be a very appealing concept––but what does it really mean? Let’s break it down into its two components.

Defining Your “Greener Grass” Is

To find your personality in your career, first define what success means to you. We aren’t in law school anymore, living in a fishbowl of germs and competition. We are grown professionals, who need to worry about what makes us happy, fulfilled, and challenged. We need to focus on how we can stand out as a leader in our field, not what others might think about our short-term or long-term personal goals. What success means to you might be very different from what success means to me. You may have different financial needs, family obligations, interests, strengths, and goals than any other lawyer in practice right now. So finding your successful path takes guts, to avoid falling into the trap of comparing yourself to the herd.

In my own career, I found myself making lateral change after lateral change, always hoping to find that the grass was “greener” on the other side. But I did not spend the time needed to define what “greener” was for me.

What was I looking for to be better? I was reacting and bouncing around, based on what others were saying would be better for me. Instead, I wish I had gotten in touch with my priorities and goals so that I could proactively paint the picture of what I wanted, and go get it.  When I finally began working with a career coach, it was a game changer for me.

Finally I realized that no matter how awesome the firm job I landed (I had some awesome jobs), none of them were meeting my goals, since what I really wanted was to work for myself. Maybe your deep dark secret is that you want to work for a non-profit, work from home, or have more client interaction. Whatever it is, you need to understand that personal need before you make a career change. The saddest thing you could do is to invest time, money, and energy into changing jobs, only to find that the new position is no better of a fit for you. Trust me.

Prevent Burnout by Understanding Yourself

Because we are all unique, things that energize me (I am a major introvert) might bore you (my extrovert husband can attest). Office settings or workloads that might energize you could terrify me. Getting in touch with your personality type is so important not only to help you thrive in any work setting, but also to proactively identify what type of setting you would thrive in. So many lawyers who are burning out quickly in their careers are great lawyers and great professionals, but in a position or setting that is totally out of line with their personality, personal priorities, or family needs.

Setting yourself up for a sustainable career is just as important as being in a successful career. If you are a rockstar associate but burn yourself out in 5 years, what good was that short success?

Part of preventing burnout is understanding what boundaries you need to set, how to communicate with your colleagues to demand and earn respect, and when to delegate. Some of the most important skills you need as a lawyer are not taught in law school; they are learned as part of experience and life. But I hate to see lawyers learn the hard way and ignore signs of burnout, until they can’t see any way out other than to leave the law entirely or make drastic changes in their life that feel reactionary.

You’re Not the Only Path-Seeker

When I was frustrated in my jobs, I felt very isolated. I couldn’t talk to my friends at work about what was going on, since I didn’t want to put them in awkward positions. I couldn’t talk to my friends who were still looking for jobs, because I felt very ungrateful for not wanting the job I had. I had a hard time talking to my family, since I didn’t want them to think I was a quitter.

There is no shame in wanting to find a path that allows you to thrive and find success. Don’t be ashamed if you didn’t hit a home run your first time at bat.

Chelsea Callanan of Happy Go Legal
Chelsea Callanan of Happy Go Legal

If you don’t want to navigate this journey alone, you can join others who are trying to find successful and sustainable legal careers. Happy Go Legal is offering its first ever Right Path Group Program, aimed at helping you utilize resources and books that complement my coaching style, to make some big decisions, that could benefit the rest of your life and career. If the group setting isn’t for you, there is also a Right Path Laser Assessment that might be more up your alley.

Interested in learning more? CLICK HERE – the Group Program starts September 17, 2013 and has limited seats, so act now! And because Chelsea loves collaborating with and supporting the Leaving the Law community, enter Discount Code HGLGroupPath to receive $20 off whichever program you feel is a good fit for you.

Chelsea Callanan is a practicing lawyer, blogger, and career & life coach – she founded her company, Happy Go Legal, to provide resources and education that inspire lawyers to prioritize professional development and work-life balance issues. Her number one suggestion to lawyers? Take time to identify what it is you’re working toward, and what achieving it will mean for your life.  Only then will you find success and sustainability.  Hear the rest of Chelsea’s story about how coaching changed her life and career and consider whether it’s time to take your career into your own hands.


  1. Very good post. A game changer for me was also, after lateral moves (including to one at my state’s most prestigious and high-paying firm), realizing that no large law firm would ever make me happy or help me “succeed.” A bit scary in a profession that pushes law firms at everyone but necessary for future happiness (I also need to have my own biz, though I can accept collaborating with the likeminded).

  2. Excellent advice. When I was a younger lawyer, I was given this type of advice, but never really heard it. After 22 years as a lawyer I can now say that getting to truly know yourself and what you really want is by far the most important thing you will ever do for your career. And it’s not just what others consider to be the important stuff, either. For example, if your surroundings are important to you and you can’t think straight in a cluttered, disorganized environment, don’t ignore that aspect of your personality. If it’s important to you, then it’s important!

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