How Lawyers Can Stop Being Risk Averse In Their Careers

How Lawyers Can Stop Being Risk Averse In Their Careers

Since childhood, I’ve had an intense fear of the ocean. Part of that fear stems from watching Jaws one too many times, but another part is a result of not being able to see or touch the ocean floor the further out you go from the shore. I acknowledged and recognized this fear about nine years ago when I was training for a race and decided to do an open water swim in Biscayne Bay in Miami on a Saturday morning. I still remember the panic I felt in not being able to see the bottom of the bay or what lied below my feet.

The fear of swimming in the ocean or bay is only one example of a seemingly obvious risk aversion. I’ve always weighed options to a fault and agonized when making decisions that present an “unknown.” When I pack for a trip, I think about every possible scenario that can happen, so I overpack toiletries, medicines, and clothing items, 75% of which don’t get used. Sometimes, my own anxiety about making decisions creates “analysis paralysis.” All the “what ifs” play over like a broken record in my mind.

Where did all this stem from? Since when did I become so hyper-focused on the fear of the unknown?

Lawyers, by their very training, are conditioned to be risk averse. From the time we enter law school, we are confronted with issue spotting hypothetical scenarios (i.e., the piano falling out of the window of the 80th floor of a building), delving further into seeing things from many angles, and always answering with, “It depends.” I chuckle as I think about the time in the bar exam prep course when the instructor said, “You will reach a point when you’re down to two choices, A and B. You agonize over which one to pick. A? B? A? B? Circle one and move on.” In theory, he’s right, but if you’re anything like me, you will agonize for a good five to seven minutes in the timed exam, select one, analyze that choice, analyze it some more, and contemplate changing it before you’re ready to move on.

I grappled with the fear of the unknown for many years into the practice of law and in my legal career — the uncertainly of not knowing what was on the other side of law as well as the uncertainty of what people would say if I left law to do something else. Yet, I had lots of mental roadblocks for nearly 12 years that hindered my happiness. What if this happens, then what do I do? What if I go this route, where will I end up? What will I be giving up instead?

My overanalytical nature prepared me well when I made my departure plans to leave law.

What if I didn’t bring in enough monthly cash flow from client projects? I created a nest egg to keep me afloat. I looked at where I was spending extra money and started to get honest with my finances. I began to live more frugally and made a financial plan before I would leave law. I gave myself a time frame to save up before taking the leap.

What if a recession hit and I stopped getting my target clients? I made an action plan on how I could pivot and leverage writing for new clients or leveraging my writing in new ways. It forced me to continue building up my writing portfolio and diversify it.

As time went on and I made my plans to leave the practice of law, all the “what ifs” started to feel less heightened. I thought of potential situations and I wrote solutions out. I made lists of pros and cons. I cross-referenced a checklist of goals. I had my life jacket ready for the next open water swim. Then I just did it. I stopped being so risk averse because I knew that if I didn’t take the leap in my career, I would always be left wondering what could have been. I would have rather failed and said at least I took the leap, than sat with paralyzed fear wishing I had done it.

If you’re at the point of wanting to leave law or wanting to take your legal career in a different direction such as going from Biglaw to in-house, here’s my advice: make your plan and act. The only thing that’s holding you back is your risk aversion.

Wendi Weiner is an attorney, career expert, and founder of The Writing Guru, an award-winning executive resume writing services company. Wendi creates powerful career and personal brands for attorneys, executives, and C-suite/Board leaders for their job search and digital footprint. She also writes for major publications about alternative careers for lawyers, personal branding, LinkedIn storytelling, career strategy, and the job search process. You can reach her by email at, connect with her on LinkedIn, and follow her on Twitter @thewritingguru.  

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