Career Transition: A Case for Making the Leap (Part 1/2)

I used to get the question at least once a week: Do you miss being a lawyer? Do you think you’ll ever go back to law? When do you think you’ll go back to law? Are you happy with your decision?

The questions, I know, came from a genuine place of curiosity and, more often than not, love and concern. And each inquirer had their own underlying motivation for asking. Most sincerely wondered how someone could invest so much into such a well-regarded career and simply walk away from it. Some were wishing they, too, could make the leap and leave their own law firm job. Some were waiting for me to admit it was a colossal mistake. Some were really wondering if I had just completely spiraled out and totally lost my mind.

Here’s the thing. They were fair questions.  Inside of four years, I had finished law school, launched into my career as a corporate lawyer, bought a house, had not one but two babies, started a nonprofit initiative, and had finally decided I could no longer make my then 13-year marriage to my high school sweetheart work. When I announced just two years later that I was now leaving a career I had invested so many years and hella dollars into, in hindsight, I really can’t blame people for thinking I had finally lost it.

But I hadn’t. While my decisions at the time may have seemed erratic or unthoughtful - impulsive even - they were far from it. The personal decisions I had made just a couple years prior had given me a reason and opportunity to evaluate my professional path as well. Was this really how I wanted to be living my life? Was law the profession I dreamed it would be? Could I imagine myself spending the next 40 years of my life in this job and retiring from this career? That had certainly been the plan up to that point. But it was starting to feel like maybe it wasn’t the best plan going forward.

Analyze This

I spent three years - from the time I had my first stirring of doubt to the time I made the leap - figuring out exactly what my next move might look like if I were actually to make a change. Big changes are risky, and I wanted to be very clear on what I wanted from this move. I needed clarity on what I was good at, what I was not good at, what I enjoyed about my actual work (and what I did not enjoy), the structure of my days, how I would want my career to grow and evolve over time, and how I would close the financial gap between a law school education and a non-legal career.

While I had spent six years becoming a talented lawyer at the largest (and best, IMHO 😉) firm in the city, I didn’t enjoy practicing law. Most lawyers are energized by digging into cases and crafting *the argument* that will save their client thousands of dollars or win the case. I wanted to fall out of my chair every time I had to print off a new stack of cases and pour through pages and pages of case law or dial into the minutia of yet another contract provision. I found it incredibly boring and, looking back, that boredom was preventing me from reaching my full potential.

But firm life wasn’t all bad! What did I enjoy? Margarita Fridays with the other associates, for one. But…on a more serious note, I loved marketing the firm. I loved business development and the challenge of growing my own client base and that of the firm. I enjoyed promoting the firm in the community, serving on nonprofit boards, building relationships, meeting and getting to know other business leaders, and sharing how our firm could serve their needs. The real irony in this was that I had entered law school an incredibly shy young woman, and wanted only to sit behind a desk and paper deals all day. However, to get a law firm job, I was forced to come out of my shell, and my firm encouraged us to get involved in the community and build our network from day one. For some reason, I accepted both of these challenges and ended up not only loving it, but thriving in these environments.

During this time, I also started a nonprofit and found that I loved the thrill of rallying other leaders around a common goal of supporting and funding a program - in this case, promoting youth entrepreneurship in our community. Also at play was the fact that I had always wanted to be in a corporate role - to be working in the business. Being a corporate lawyer sometimes felt a bit like doing all the tough research and analysis then throwing all that work over the wall to the real decision makers. I wanted to be part of the decision-making and, during this time of soul-searching and analyzing, this desire only heightened.

Decision Time

I dipped my toe in the water a few times before making the ultimate leap from my firm position. Of course, the thought crossed my mind initially whether I should consider a different firm. I think that’s a natural question any time you’re considering leaving a job - whether a competitor is a better fit. However, for me, that option was quickly dismissed. I knew I was with a great firm with even better people. Law firms are mostly created equal, and I was convinced I had landed at one of the best. It would not have solved my issues to switch from one firm to another. The next natural question for me was whether to go in house, and I explored a couple of in-house positions. This would have been a ridiculous move though, given that the very thing I disliked most about my current career was the legal work itself. It would have put me in a role where I would be doing everything I hated about my current job and nothing I loved.

When it came time to make the leap, I decided business development was where I needed to be. I explored a couple opportunities and ultimately accepted a position with a nonprofit organization to lead their fund development and stakeholder engagement efforts with local business leaders. I truly could not have found a better fit! Even then, however, I knew this position could serve one of two purposes in my career: (1) a transition role; or (2) a long-term role. It was a nonprofit - not exactly corporate, and not exactly answering that all-important financial gap question. But in every other way, the role was full of opportunity and could not have been a better fit had I designed it myself. Which is, in fact, what I ended up getting to do…designing my own role.

The Second Act

When it started to become evident two years into this position that it would likely be serving as a transition role in my career, I began preparing for my second (and presumably final) transition. This time, I worked with an executive coach to help me better understand myself, my strengths, weaknesses, and what types of roles I should be pursuing. The coaching helped provide the clarity I needed to realize that if I was serious about my continued growth and development and achieving my career goals, it really would be necessary for me to leave the organization I was with - a decision I was struggling with because I enjoyed the work. However, I had achieved the goals I had been hired for, had successfully taken on other initiatives, and the opportunity for continued growth and development in that organization simply did not exist. If I stayed, I risked severely limiting my potential and my career. So, once again, I set a plan in motion and leapt.

I’m well into the second year of my new role and know I’m on the right path. The years of self-reflection, analyzing, waiting, and transitions have proven fruitful to lead me to this point. My current role requires entrepreneurship, leadership, accountability, creativity, business acumen, and a whole host of other skills that I have been developing over the years. It is challenging, demanding, and so much fun. I am grateful every day I had the courage to make the shifts and go through the sometimes long and scary process of getting to this point because I am now reaping the rewards in a level of job and career satisfaction I have never experienced before.

Although I have a great deal of clarity and vision for my career path from this point forward, I know it will naturally include a lot of twists, turns and surprises because I will never stop evolving and trying new things. I have built that flexibility into the ongoing plan. I continue to be open to what the world has to offer and I’m excited to see where life takes me!

I always get a lot of questions when I share my career journey, and NEXT I’ll be posting Part 2, where I’ll share some of my best advice for making career shifts.