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Failing to Succeed: How Design Thinking Taught Me to Embrace Failure

As part of the coursework for Legal Problem Solving (LPS), all students contribute a post to this course blog. Students develop posts from a weekly journal entry, which also is required coursework. The purpose of journal entries is to invite deeper, personal reflection on the subject matter in LPS, reflection being a key component of content understanding and mastery. This course explores how human centered design and other creative problem solving methods and mindsets inform three areas: (1) the delivery of legal services, (2) how we solve clients' (legal) problems, and (3) how law students can intentionally shape their professional journeys. Each student post will touch on one or more of these three areas.

This LPS post is by Sarah Routh, Vanderbilt Law School class of 2018.

Panic. That was the only thing racing through my mind as I was told I had seven minutes to build a prototype of an idea that I had developed a mere few minutes beforehand. The task at hand was a design sprint. This required me to develop a solution to a problem that I had teased out from my partner, who was somebody I had just met the same day. Over the course of an hour and a half, I was supposed to pepper my partner with questions, make inferences about his impressions of law school, and develop a solution to a problem that I believed he had with the law school program. The assignment was daunting ​to say the least.

In our Legal Problem Solving class, my fellow Vanderbilt Law students and I are taught to approach the legal profession from a design thinking perspective. A key component of design thinking is the core mindsets, which we are supposed to embody when we implement this process. While some of these mindsets came naturally to me, such as empathy and asking for help as I am admittedly a sucker for team projects, one was extremely hard for me to embrace: failure. According to Creative Confidence authors Tom and David Kelley – partners at IDEO, an innovation and design firm, and the latter a creator of the at Stanford University – the essence of this mindset is to have “more success, you have to be prepared to shrug off more failure.” Underlying this concept is the idea that failure is inevitable and that success is born out of an individual’s propensity to embrace that concept and learn from past failures to improve upon her prior attempts.

In my mind, this mindset contradicted everything I had been taught growing up. One was supposed to know the answer ​on an exam or else she would fail and be unable to get into the college of her dreams. Everyone wanted the first place trophy at the latest sporting event, not a participation certificate. A girl had to pull off a killer first impression on a first date with a guy she liked otherwise there would be no follow up date with him. This was the perspective of failure I had going into the first day of my Legal Problem Solving course.

This perspective tainted my academic and professional experiences. During my 1L fall semester, I would spend hours meticulously dissecting the cases I was assigned and putting them into intricate case briefs that were nearly as long as the cases themselves. I would then contemplate questions my professors might ask me in class the next day and rehearse my answers out loud so that I would not be “that girl” in class who messed up a cold call. If I felt that a cold call had gone awry, I would beat myself up over it despite being reassured that I had sounded smart, and regardless of that, nobody was paying attention.

At my job this past ​summer I faced similar obstacles. Anytime I received an assignment, I was so determined for it to be pristine without realizing that this was a learning opportunity for me and that the attorneys did not expect perfection, especially in terms of legal analysis. My fear of failure paralyzed me, and I often found myself spending countless hours on any given project to ensure that my work was perfect upon completion of my first draft. As one could imagine, this was not an ideal situation for a young summer associate whose work was tracked by billable hours that were charged to a client. This fear of failure even seeped into my personal life, preventing me from joining a beginners’ – yes I said beginners’ – tennis clinic for fear of embarrassing myself in front of the rest of the class due to my inexperience.

My perspective on failure began to change gradually over the course of the semester thanks to my Legal Problem Solving Class. ​Initially I came in very skeptical of the mindset, thinking that young associates were always expected to be perfect and did not have the time or the luxury of making a mistake on the job. Slowly, I began to frame failure in a different way. I began to take the Kelley brothers’ advice and accept the inevitability of failure, and instead of torturing myself once it occurred, I would assess the situation in which I had failed and try to learn from my mistakes. Upon my second try at something – whether it be a cold call with my Professional Responsibility professor or a presentation in front of my Drafting professor – I would be cognizant of what went wrong in the past and implement new techniques that I believe would work better.

Furthermore, I began to use the tools the Kelley brothers delineated in Creative Confidence that would help me get over my fear of failure. For instance, in the chapter entitled “Leap,” the Kelley brothers suggest that individuals who find themselves procrastinating on projects due to a fear of the final product being unsatisfactory engage in something called the “do something” mindset. Specifically, they state that those who have the “do something” mindset “recognize that waiting for a perfect plan or forecast might take forever, so they move forward” and correct any mistakes after they begin the project. Subsequently, the Kelley brothers make some suggestions as to how to engage in this mindset in the form of “action catalysts.”

I have found the “gather an audience” catalyst to be an extremely useful tool ​as someone who – as stated earlier in this post – loves teamwork. This tool requires an individual to seek out people with whom to share their ideas out loud and potentially solicit feedback from them. Now whenever I have an issue with an assignment, I talk to anyone I think may have any knowledge of the subject matter of that project – such as my law school friends or my family members – with whom I can discuss my ideas to see if I am on the right track. Sometimes I even discuss these ideas with someone who is unfamiliar with the topic just to hear my thought process out loud to assess if I am making any progress. This tool is one of the many “action catalysts” that I have found myself using on a more regular basis.

Now that I am reaching the end of the semester in my Legal Problem Solving class, I am delighted to reflect on my progress with embracing the failure mindset. Naturally, I continue to try hard to ensure that I produce high quality work. Nonetheless, I no longer spend unnecessarily long hours mulling over an assignment, convinced that my first stab at it has to be the best work I have ever created. I have signed up for that tennis clinic, although I still say “oops” every time I do not hit the ball – this is clearly an ongoing process. Finally, I attended a second design sprint, and I am happy to report that I successfully created a prototype, anxiety-free, that I was proud to show to my partner upon completion.