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June 10, 2021

What Is the Risk That You Took (or Didn't Take) In Your Career That You Most Regret—or Are Most Satisfied With?

May 20, 2014

Full disclosure, I am a risk taker. My comfort level with taking risks comes from my years playing and coaching college women’s basketball before applying to law school. You cannot score if you do not take the shot, right?

A recent and rewarding risk I have taken in my legal career was moving from a high-stakes litigation boutique to a smaller minority-owned civil practice law firm, White & Wiggins, LLP. I knew little about W&W, with the exception of partner Camille Stearns Miller, whom I highly respect. Quickly, I learned about the firm’s history as the senior minority-owned law firm in North Texas and the importance of its presence in the Dallas Bar.

Notwithstanding the firm’s history, my friends who practice at large majority-owned law firms questioned my decision to move to a smaller firm. In the end, I had to rely on faith. Fortunately, I currently work in a more collegial environment with professionals who are zealous advocates, but more importantly, good people. As a working mother and wife, W&W provides me the opportunity to manage my work-life commitments without affecting my goal to always provide quality legal services and counsel to my clients.

This time, I scored.


Amy M. Stewart is a senior associate with White & Wiggins, LLP, in Dallas, Texas.

The greatest risk that I took was in leaving my position as a partner at a New York City law firm to go in-house after almost 15 years of practice. At the time, an opportunity presented itself to me for a position that I believed would provide interesting work and great career opportunities in the long term, but I was also mindful of how much I was giving up and how hard I had worked for my credibility and reputation within my law firm. In the end, it was a risk worth taking. My skill set has expanded immeasurably to include a broader appreciation for the various stakeholders that are clients in an in-house setting and the necessity of exceptional consensus-building skills for success in a corporation. These are skills that I know will serve me well, wherever my career takes me.


Patricia O’Prey is senior counsel in Litigation & Investigations COE at GE Capital Corporation.


The risks I’ve taken in my career have all worked out, even if there were some bumps in the road. After a two-year clerkship, I joined a well-regarded litigation boutique. During those years, I built my litigation toolkit by working with some of the finest trial lawyers in Philadelphia on a wide array of cases. After five years, I lateraled to a large international law firm to focus on financial services litigation. There, I made partner while on maternity leave with my first child. Three years later, when my second child was an infant, I took a three-day bar exam to lead the litigation department in a smaller firm office in a neighboring state. I try not to waste time and energy on regret, but that was tough with two small children. I had a very supportive husband, a great nanny, and my children were thriving.

As I approached my 40th birthday, however, I was not thriving. After much soul searching, I concluded that my satisfaction was rooted in growing my own practice. For every three calls I received about a new case in the large firm, however, I had to turn away two for conflicts. I took a risk, joining the Philadelphia-area office of a Houston-based firm focused on tax controversy and related litigation. It wasn’t the obvious decision, but it was a good one.

One year after changing firms, I have a steadily growing practice handling litigation related to joint venture and other business dissolutions. I work with talented lawyers whose specialties complement mine in a collegial environment. I recently joined the advisory board of a legal services startup. My network has blossomed. But the biggest improvement, and it might sound silly, is that my home, my office, my husband’s job, and my children’s schools are all within a five-mile radius of each other.

Taking risks is vital to continued growth and satisfaction. I was lucky to have incredible mentors and advisors at every step of the way. At the same time, there are always unknowns. Getting comfortable with the unknowns was a challenge for me, but it was well worth it in the end.


Elizabeth S. Fenton is a shareholder at Chamberlain Hrdlicka, West Conshohocken, Pennsylvania.


May 20, 2014