Return to site

Learning to Fail

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 Shannon Vreeland, Vanderbilt Law School class of 2019.

Success is going from failure to failure without loss of enthusiasm.


– Winston Churchill​

Early in the semester, as an assignment for Legal Problem Solving, we read a book called “Creative Confidence.” The tool or idea that stuck out the most to me throughout the book was the concept of a failure resume. After thinking about it some more and writing about it in a journal entry, the idea that this is a concept of great importance to lawyers and law students was reinforced during a classroom presentation, when one of our professors mentioned that lawyers are substantially worse than the general population at dealing with failure.

That’s certainly a statistic I did not second-guess, as it just makes intuitive sense. Now, this statistic could be attributed to a variety of causes. For one, a lot of ink has been spilled on the effects of social media on feelings of perfection and anxiety. Although social media is a relatively new phenomenon, the already competitive enterprise of law practice, coupled with the feelings of competitiveness with peers could certainly heighten the fear of failure. Further, women in the workplace have generally tended to exhibit symptoms of imposter syndrome and other anxieties related to the need to be flawless at their jobs. With law students and attorneys, however, this isn’t just an issue confined to the social media users and women in high level positions. Lawyers and law students are, and have historically always been, high achievers who have likely experienced little failure before they get to the study and practice of law.

I like to think I’m good at failure. Growing up an athlete and competing on an international stage, I learned that you can work for years and give your absolute all and still come up short. You can dislocate a shoulder or get sick the day of a big competition and not have the success you desired, or you can make the biggest competition of your life, have an off-day, and risk embarrassing yourself in front of friends and family and also potentially all around the world. It’s a lot of pressure, and I assumed that my ability to rebound from the string of failures I had throughout my own swimming career would translate to law school. I quickly realized that while I didn’t necessarily let one bad grade get me down, and I took big failures in classes like legal writing as an opportunity to improve, not to give up on myself, I started to ​fear failing in ways I’d never experienced before.

Unsurprisingly, research suggests that many lawyers’ fears of failure develop during law school. Students are under the stress of a heavy workload, getting good grades, searching for jobs, searching for clerkships, and on top of all of it, constantly being pitted against classmates and friends.

For me, my biggest fear of failure was humiliating myself in front of my peers. Whether that was running for and not winning a spot I wanted in our student government, messing up or fumbling words or legal issues on a cold call, or failing in an aspect of the job or clerkship search, law school set me on a path early on where the confidence I’d developed before I arrived at law school was suddenly gone. I was scared to admit ​weakness, or be perceived as inadequate to my peers. As a person who spoke publicly any number of times to large crowds confidently and happily, I would suddenly break out in an actually visible anxiety rash at the thought of speaking in an oral argument or even simply speaking up in class.

While I’ve gone, most noticeably, the last few months feeling like I was alone in my crippling fears of failure, a survey conducted by Yale Law School that I found when trying to search for more information on Professor Bridgesmith’s statistic from class made me realize I was, in fact, far from alone:

Students described a culture where being stressed is seen as a “badge of honor,” where "competition is palpable," and where students, faculty, and administration all place an inordinate amount of emphasis on "winning the rat race." On the one hand, respondents to the survey reported a persistent fear of being perceived as “stupid,” and on the other hand a belief that peers who admitted to feeling overwhelmed or inadequate were unable to handle the pressures of law school.

How exactly do we help students that are already perfectionists fearing failure to be ok with accepting a little bit of it in their law school lives? One way that we discussed a little bit in our Legal Problem Solving class was the concept of a “failure resume.” In the book “Creative Confidence” the tools of a “failure resume” and of “failure conferences” were discussed. The failure resume in a book was described as a compilation of the biggest defeats and screw-ups poured out in resume form. For Johannes Haushofer, an assistant professor at Princeton, it was a “CV of Failures” listing degree programs he did not get into, academic positions and fellowships he didn’t get, awards and scholarships he did not receive, and my personal favorite, his “Meta-Failure” in that “This darn CV of Failures has received way more attention than my entire body of academic work.”

An important part of the failure resume is that it highlights how success actually works. While writing an article about the CV of Failures idea, Melanie Stefan concluded that ignoring setbacks leads to a false perception of how success actually works. She noted that “[a]s scientists, we construct a narrative of success that renders our setbacks invisible both to ourselves and to others. Often, other scientists' careers seem to be a constant, streamlined series of triumphs. Therefore, whenever we experience an individual failure, we feel alone and dejected.”

Sound familiar? To me, that sounds exactly like law school. We don’t discuss our failures. We are told from day one that somewhat of a checklist exists of all of the things that need to be accomplished in order to find success in the legal field, even though accomplishing them all seems nearly impossible, if not impractical, should you want to also get some sleep and maintain your sanity. So we see the ones who do seem to check all or most of the boxes as having some infallible stream of success, and every failure we experience seems unique and amplified. In fact, we discuss failure so little that any mention of it is novel. I was told that my cover letter was “refreshing” at an interview this summer for the sole reason that I discussed my fairly extensive stream of failures leading to the end of my swimming career and learning/rebounding from them “instead of simply listing off successes.”

Melanie Stefan isn’t the only one creating failure resumes. Bessemer Venture Partners, one of the country’s oldest venture capital firms does something similar with its missed opportunities for investment. Their public "Anti-Portfolio" lists the companies they have passed on, noting that their “long and storied history has afforded [the] firm an unparalleled number of opportunities to completely screw up” and even better, it lists the range of reasons for passing on investments. For example, reason for passing on investing early in Ebay: “Stamps? Coins? Comic books? You've GOT to be kidding," thought Cowan. "No-brainer pass.”

Melanie Stefan’s suggestion is to compile a list of failures. Log every application that was rejected, all of the times you tried and then failed and even though it might be depressing when you first look at it, it will remind you of truths and where your journey has taken you. Further, making the lists public remind others that the failure is not the end of the world. While I don’t think all of us are at the point where we can list our failures publicly and jokingly, it’s certainly an interesting place to start.

Elon Musk has an infographic resume of failures. Silicon Valley hosts an entire conference dedicated to failure, FailCon, a conference whose point is not to celebrate failure, but to learn from it. Newcomers to the start-up industry meet with industry veterans who lead discussions like “How to Conduct Yourself When it all Goes off the Rails.” A different company has an idea they have called the “Failure Wall,” where you describe a time you failed, write what you learned, and sign your name. The CEO of that company in fact also claims to hire people who fail, noting that when you succeed, you don’t always know what you did right, but when you fail, you have to take a look back and reevaluate where you went wrong and make a new plan for next time. Finally, in an Above the Law article, one author suggests that taking a page out of a BigPharma company and recognizing and appreciating failure is something that could help lawyers to feel appreciated in their work, like champagne after a big deal, whether the deal ends in success or not.

I understand we don’t always want to celebrate failure. But clearly, people respect failure and what we can learn from it in a wide variety of ways. We’re not going to win or succeed in every aspect or facet of life and the law, and learning to take the time to not suffer in silence from perceived failures, but to learn, grow, and respect where our failures may take us could lead to a happier and healthier path through law school and our chosen career paths.