“Ever tried. Ever failed. No matter. Try again. Fail again. Fail better.”

 -Samuel Beckett

 1.  A Lawyer Blunders

Some twenty years ago, a feckless young lawyer nearly lost his first client. The lawyer had negotiated what he assumed the client would agree was an unusually handsome settlement offer, an offer whose obvious appeal needed no explanation. And so, he provided none. No explanation about the settlement process, the law, or the negotiations themselves. Nor in his haste did he allow the client to ask questions, all the while asking none himself. Instead, he jauntily announced the dollar figure. Then he smiled and awaited his client’s certain gratitude. But her eyes narrowed as crease-lines broke across her brow, marking her face with misunderstanding, or worse, mistrust.

In his next case, the lawyer’s self-absorption in the merits of his motion rushed him to secure an ex parte order against opposing counsel, denying her the chance to explain or defend. It was a short-lived procedural victory at the cost of a long-term professional relationship. The disappointment in opposing counsel’s voice when she called the next day punctured the young lawyer’s inflated posturing, exposing the self-inflicted wound to his integrity.

The lawyer’s penchant for error surged in his next case. Worried about the potential damage of unwelcome facts against his legal position, he answered the judge’s question with a half-truth. His answer was “technically” and narrowly correct. It was ethical, strictly speaking. But the answer was also deficient, deficient because it avoided truth, deficient because it distorted truth. Opposing counsel pointed out these deficiencies by kindly referring to the lawyer as having “inadvertently misspoken” on certain matters of fact. This was at once rhetorically generous of the older, more experienced opposing counsel and, in the same deft stroke, devastating to the younger one.

Although the young lawyer meant well in each case, his mistakes sprung from equal parts vanity, haste, and inattention. In each case, too, he slighted a vital member of the legal system – the client, the opposing counsel, and the judge. The lawyer more than slighted himself. His missteps laid bare the first wounds of early professional failure. Those wounds would run deep, prompting the lawyer to question his competence, to worry over his reputation, and to soak in his own well-deserved embarrassment. He fretted daily; self-doubt had set in.

But then, with little passage of time and even less thought, the lawyer forgot his mistakes. Or maybe he denied them to himself. Or perhaps he misremembered or reinterpreted them. Anyhow, he moved on. And that was his biggest mistake of all.

As with the young lawyer, forgetfulness on the heels of self-doubt can quickly become the habitual response to professional failure. To be sure, we all face the inevitable, formative letdown, the early career flop none who enter the legal profession can avoid. It happens to us all, and not just at the beginning of our careers, though our earliest blunders might flash brightest, if not briefest, in our memories. Yet we soon dim the memory of those mistakes, relegating them to dreamy insignificance, or we deny our failures outright, dismissing them as trivial or empty in the larger scheme of things. We shrug them off, just like the young lawyer.

If later forced to bear their burden or called to account for them, we reinterpret our mistakes as having worked out well after all, and we massage our history of screw-ups to coddle our self-esteem. We erase the cognitive dissonance our past faults triggered. In equally dismissive fashion, we might pay lip service to “learning from our mistakes” when in truth, without further ado, we forget the lessons, if indeed we ever learned anything other than to soothe our bruised egos.

In the reflexive grip of these habits, how can we lawyers learn from our mistakes? Fortunately for us the answer is emerging from decades of cognitive science research. Cognitive scientists now tell us the answer lies in somewhat counter-intuitive career advice: we should seek out ways to make mistakes. We should experiment with failure, they say. We should lose, lose often, and lose without great cost. In other words, we should invite mistakes we can survive, the kind from which we can recover, and then adapt. This last insight may be most crucial: it is our capacity to adapt to mistakes that determines whether we wilt or we flourish. In the end, our success always starts with our failure.

At least it did for me, in a series of early career blunders, a string of shameful gaffes I tried at first to deny, forget or reinterpret, only to realize much later in my professional life their empowering lessons. I hope to share some of those lessons with you, so that we might all learn from our mistakes as lawyers. For you may now see that the once young lawyer who blundered with his client, with opposing counsel, and with the court is – me.

And while I make no claims to error-free legal practice today (far from it, in fact), I can affirm that whatever fulfillment and flourishing I enjoy as a lawyer – nearly two decades later – is largely the hard-won result of embracing my failures. In short, I’ve come to practice the art of losing. It is a subtle, searching art of self-discovery that ironically enough plumbs the depths of our mistakes as a necessary step towards wholeness and mastery in our difficult, challenging profession. The art of losing encourages us to make mistakes, survive them, and then adapt. We try again. We fail again. We fail better.

2.  A Few Uncomfortable Truths About You and Me

Warming to the art of losing forces us to confront a few uncomfortable truths about our mental lives. Take, for example, how we instinctively excuse our past failures and see ourselves as more intelligent, more successful, and more skilled than we really are. This is known as the “self-serving bias,” and it rules our mental roosts. We all tell ourselves we are wonderful, which isn’t entirely misguided since it avoids stagnation and lassitude. To obsess over our daily failures would shut us down with anxiety. Perhaps that is why evolution favored our ever-vigilant inner spin doctor.

So vigilant, in fact, that our inner spin doctor automatically slants our perceptions of the social world in our favor, leading us to believe poor outcomes are the result of other people’s mistakes or factors outside our control. By the same token, when things turn out well we credit our legal genius to the exclusion of all other causal factors. If we win our case, it was our brilliant tactical maneuvering. But if the other side wins, it was their dumb luck. Such cognitive distortion prevents intellectual honesty and defeats our ability to learn from our wins and losses. As a consequence, the next case or client may suffer.

The self-serving bias stems from cognitive dissonance, the fact that our minds can’t comfortably entertain two simultaneously opposed ideas. “I’m a well-qualified, capable attorney” clashes with “my mistake reveals my incompetence.” The result: we instinctively refuse to accept the mistake that might imply our incompetence. Our minds do not naturally or easily separate our errors from our sense of self worth. The latter, left to the automatic operations of the mind, almost always trumps the former. We rapidly jettison error to preserve ego. Once again the error goes unrecognized.

Cognitive dissonance is not the only enemy of error recognition.  We also self destructively chase our losses. Known as the “sunk cost fallacy,” such faulty thinking causes us to devote more wasted time and resources trying to undo past mistakes. For instance, we hang onto losing cases and failing client relationships by concocting seemingly rational reasons to justify beliefs and behaviors in which we’ve made sizeable investments. But past investments should not necessarily influence future decisions. If we were truly rational, we would compute the odds of succeeding from each point forward and decide if more investment warrants the likely payoff.  But, alas, we are not rational.

It gets worse. To the extent we are rational, reasoning can take us to any conclusion we want to reach. Research now confirms that when we want to believe something, we subconsciously ask ourselves “Can I believe it?” But when we don’t want to believe something, we ask ourselves “Must I believe it?” We answer yes to the first and no to the second. Applied to our mistake making, this kind of reflexive “reasoning” yields the self-justifying, face-saving answer we want. Further complicating our own error detection, we’re all obsessed with what others think of us, whether we know it or not. Our desire to fit in and our need for social approval motivate our reasoning to self-justifying ends. Those ends, as we know, distort our ability to see our mistakes.

Yet another cognitive bias stifles our awareness of personal error: “hedonic editing.” Otherwise known as “rose colored glasses,” this is the subtle process of convincing ourselves that our mental “intake” doesn’t matter. No matter the objective input from experience, we see only the positive subjective interpretation. This comes in many forms and is closely allied with the other biases we’ve surveyed. So, for example, peering through our rose colored glasses, we might reinterpret our past failure as a success. Or we might rationalize that our failure wasn’t that bad after all. Or, to our happy surprise, it actually worked out for the better that we made the mistake! The upshot here is that we systematically reinterpret bad decisions as having actually benefited us. This, too, is a deeply ingrained feature of our minds.

Many other biases and cognitive flaws disrupt clear thought. Knowing about our self-serving mental machinery is only the beginning, a vital preliminary to the art of losing. We must first recognize that we’ve made a mistake before we can do anything about it. Many of us fail at this nascent stage. Our subconscious minds come automatically, instantaneously to the aid of our bruised egos, leaving little time for reflection. Even so, the simple nonjudgmental awareness that we “mindlessly” wash our errors in self-justifying reassurance can, in and of itself, render us more alert to our capacity for error. While mindfulness is no cure, it surely helps the diagnosis. A little self-knowledge can go a long way in the art of losing. It may not go far enough, however.

3.  The Growth Mindset

To arrive where self-knowledge fully enables the art of losing, we must briefly detour to ask why some people wilt when faced with failures whereas others thrive in the same circumstances. Answering this question takes us to the other end of the cerebral spectrum. We move from the automated, subconscious regions to the deliberate, thoughtful domains of our mind. We land in the conscious world of intentions, where attitude controls atmosphere, where our chosen frame of mind dictates our mental weather.

Consider this attitudinal experiment: you’re given a deadline to solve a puzzle. It’s not too hard. But it does challenge you. You complete it on time and you’re pleased. So you take a crack at an even harder puzzle. This one demands more mental skills or stretches your existing intellectual repertoire. You’re stumped. You fail to solve the puzzle. Time’s up.

How do you react to your failure? Your attitude, say cognitive scientists, tells us a lot about whether you will wilt or thrive in the face of life’s inevitable setbacks. Some among us – and we’ve all been there – react to such failures by saying, “This is a waste of my time, I’m bored, I’m just not very good at this.” Others, however, respond, “I can do this, I’m getting this now, this is interesting.” The two responses to the same failure couldn’t be more different. Keep in mind that neither group solved the puzzle. Both groups failed. But that’s not the point.

The point is why we respond so differently to our failures. It’s not because of our abilities. It’s not because of our interest either. We’re both capable and engaged in solving the puzzle. So, why the difference? The answer is simple, yet life-changing. Those who wilt see intelligence as a fixed trait, whereas those who thrive believe that we can boost our smarts with effort. If we believe we’re born with a certain level of brainpower and nothing changes it, then failing to solve the puzzle worries us that we’re just not as smart as we had hoped. Our failure challenges our view of ourselves as smart. So we quit.

If, on the other hand, we see effort as mattering more than intelligence, then everything changes. If we see intelligence not as some fixed quality but rather as a collection of abilities that can improve with effort over time, then we just want to get better at solving puzzles. We no longer care whether we “look smart” to ourselves or anyone else for that matter. And that may make all the difference.

Psychologists distinguish between “helpless” and “growth” mindsets. The former believe they just can’t do something because they “aren’t that smart.” The latter feel that they can master new skills and grow their abilities if they try. When they fail, they look for new strategies. They adapt. They thrive in the face of setbacks.

Changing our attitude towards intelligence alters our sense of self. We become less inclined to value ourselves based on where we rank or which rung of the ladder we’ve ascended. Instead, we incline toward intrinsic motivation, the mindset that seeks personal bests rather than winning competitions with others. Intrinsic motivation derives from our life-affirming desire for autonomy, mastery and purpose. Extrinsic motivation, on the other hand, fosters dependency on external measures of perceived success, e.g. status, wealth, and awards, to name a few. Unlike these extrinsic cues, intrinsic motivation feeds a healthier appetite for learning in the teeth of our many failures. Failures can become a kind of nourishment for our own intellectual and moral development, not judgments about our worth or status. Embracing our failures in this way, we become lifelong learners on a vast, blossoming tree of knowledge. We can joyfully explore the tree’s many branches, climbing among its many shoots, having kicked away the jealous ladder of success.

4.  Practicing the Art of Losing for Lawyers

If I could talk to the flawed young lawyer from nearly twenty years ago, I would share what we now know about recognizing our failures, adapting to them, and learning from them.

First, we’re not as smart as we think, but we can be much more mindful about our mistakes. The mind is prone to all sorts of biases, distortions, and fuzzy thinking. No matter how rational you believe yourself to be, no matter how much you’ve mastered legal logic-chopping, no matter how high your grades, your IQ, your income, or the rung you’ve climbed on the status ladder in the legal profession, you remain human – all-too-human – in your ability to perceive your own errors. Your emotional brain will almost always outpace your rational one, pushing self-serving, rose-colored and loss-chasing interpretations before your conscious mind ever gets off the starting block. But, astonishingly enough, mere awareness of this reality closes the distance between our automatic, non-thinking responses and a more mindful approach to our mistakes.

Mindfulness means practicing nonjudgmental awareness of our emotional states, especially our flash reactions to life’s setbacks. It applies equally to our more ingrained, and therefore less visible, mental habits. This awareness requires equal parts detachment and commitment. Beyond that it simply requires breathing slowly as you watch thoughts flicker across the landscape of your mind. Easier said than done, I know. Practice – much practice – is needed. But it is well worth your effort. To witness your own emotional reactions as they happen, without succumbing to their blanketing emotive force, gives you the power to respond mindfully, and not just knee-jerk when pricked by error.

Mindfulness also entails “thinking about your thinking,” much as we’ve already been doing in these pages. The first step, as we’ve said, to correcting your mistakes is seeing them as they really are. To better see your unvarnished mistakes, you must peer into the black box of your mind, which modern cognitive science now allows. Many non-fiction books popularize this burgeoning field for us lay readers.

Second, mindfulness fortifies healthier attitudes about intelligence. We can commit ourselves to the growth mindset, the practice of treating your intelligence as an elastic, emergent bounty of capabilities that can grow and adapt, not some fixed monolithic entity behind your eyes. Effort and resilience spring from this change in attitude, on account of the internal motivation that will come to drive your personal and professional development.

Finally, try new things in your law practice. Try them in contexts where failure is survivable which, most notably, means your client can’t get hurt. We should not turn our clients’ cases into laboratories to experiment with failure. Nor can we sacrifice our ethics and good judgment on the altar of self-development. We can, however, practice both mindfulness and the growth mindset responsibly to seek out ways to risk failure and adapt in our legal lives.

This is the art of losing for lawyers: Be mindful of your mistakes. Grow your intelligence. Above all, adapt. Then flourish from your failures.