Getting Past Maybe: A Call for Forward-Thinking Lawyers
Dane Lund
April 7th, 2022

Legal education mires its pupils in the netherworld of anti-probability. The goal of a legal education is to equip students with the ability to see multiple sides to an argument and to spot issues that could arise based on a pattern of facts. The process can make lawyers wildly creative: a lawyer can find latent flaws in what appears to be the most bulletproof plan, which can enable the lawyer to outwit adversaries and avoid pitfalls. The Achilles heel of the legal profession is that lawyers are trained to spot issues, not to weight their likelihood of occurring. The result is that many lawyers become overwhelmed by the landscape of potential risks and are unable to find a high conviction path forward.

In the 2000s, a popular study aid proliferated on law school campuses that aimed to distill for law students what leads to success on law school examinations. The book was called Getting to Maybe. A thesis of the book was that successful law school examinees are able to approach a set of facts and illustrate a variety of opposing results and that it was not the law student’s vocation to take a position on which outcome was correct or more likely: to see the colors of the prism, not their direction or ultimate resting place, was the goal. Possibly more symbolic than the authors intended, the cover of the book depicted a child who stood at a crossroads of five paths, with her arms extended in exasperated confusion. The job of a lawyer is often to get to the crossroad, but to take any one of the paths is the job of the client.

Getting to Maybe, Richard Michael Fischl and Jeremy Paul.
Getting to Maybe, Richard Michael Fischl and Jeremy Paul.

Getting to Maybe has proven to be an excellent resource. The authors were right, and if you follow their advice as a law student, you are better positioned to do well on your exams. As one prominent professor at Harvard Law School oft repeated: “Spot the issue, A+”.

Spotting the issue should only be the first step. In a life well-lived, it should be “Spot the issue, C minimum; make the right decision, A+”. Seeing the issues creates a powerful portal: it reduces the number of unknowns and categorizes the known-unknowns that confront a decisionmaker; but being aware of the issues only gives the decisionmaker the information needed to make a well-informed decision; it does not get anyone from point A to point B. A tradesman lawyer would counter that in many situations, there is no “right” answer. Tell that to Napoleon at Austerlitz; also, tell that to Napoleon in Moscow.

In The Brothers Karamazov, the loathsome Father Ferapont is constantly on guard for lurking spirits. In one scene he presses a monk as to whether he has seen devils. The monk responds: “You — can see spirits?” Father Ferapont:

“I tell you I can see, I can see through them. . . . I saw one hiding from me behind the door, and a big one, a yard and a half or more high, with a thick long gray tail, and the tip of his tail was in the crack of the door and I was quick and slammed the door, pinching his tail in it. . . . but [the other monks] don’t see, they don’t smell it.”

A sterling issue spotter might posit a devil — or a jackrabbit — behind any door. Spotting the issue and its derivative rabbit holes and stopping prevents what may be greater than death to a conditioned attorney: making a mistake. “I told you so” is the solace of the perennial loser. The hesitation and inaction that can arise from persistently spotting risk and avoiding it can create repulsive characteristics. It is no surprise that in Dante’s Inferno, people who could not take a position — those “wretched ones, who were never alive” — were neither welcome in heaven or hell.

The legal profession is dominated by hindering “what ifs”. The reformed lawyer reframes the “what if”. For instance, a law firm partner might worry “what if my client is audited by the IRS for structuring this merger in a novel way that has not been tested?”. A reformed lawyer (likely the client) considers: what is the likelihood that this novel form of merger bears greater tax burdens than we expected and what is the magnitude of a wrong decision here? Suppose the novel approach saves $100 million in tax for the acquiror with 90% probability but has a 10% chance of bearing a $110 million penalty (net negative $10 million). The reformed lawyer, having spotted the issue, would still go down the path, which has a $80 million expected upside; the fearful partner avoids the 10% possibility of embarrassment and forgoes the upside. His loss for certain.

Many young lawyers face decision paralysis when considering long-term investments. Almost every associate at a corporate law firm has a counter-narrative for his or her life: the thing they want to do; plan to do in the future when they have a few more bonuses; believe they could do as well as the client who is paying them. In the bursts of time when they seriously consider making a move, the carnival of potential failures comes to town: starting a business could bankrupt you; taking a salary cut to join a tech firm could mean downgrading your apartment; going to work as a non-lawyer at a corporation could mean your lawyer friends think you no longer have the same prestige.

More often than not, the imagined drawbacks are short-term pains that are necessary for any long-term success, not spiraling death scenarios. For the young lawyer, the strain of daily life at the firm calls them back to focus on document review and the rumble of daily tasks — the need to meet a deadline — helps distract them from the long term. What most attorneys do not do in their brief moments of broad-perspective clarity is assign an honest assessment of how likely the horribles they fear are to occur relative to the potential benefits. Moreover, lawyers often view the future in a series of lines, not realizing that each path before them will have multiple further crossroads: opportunities to succeed and to fail, to pivot and create something entirely new.

Eisenhower had some insight for these lawyers: “I have two kinds of problems: the urgent and the important. The urgent are not important, and the important are never urgent.” Being a steadfast service provider, responding to every “ASAP” as though it were divine fiat, is living by the urgent. Such a mindset will get you a lockstep salary and at-will employment for so long as convenient to your ASAPping overlord. A measured lawyer, being made aware of the hazards of an “urgent” mindset, will carve out time to consider the long-term, commit to an action plan that permits long-term investment (financially, professionally, and personally), and recognize that while urgent tasks must be performed, they are not to sabotage the important goals. The ability to prioritize, the courage to protect priorities, and the confidence that the downside of having a backbone is not nearly so hazardous as slipping into inaction, make for a powerful professional.

Getting back to maybe. More than five paths confront you at any given moment. Inaction is its own path that bears unknown risks. For instance, you might stay put on the partnership path, develop a highly specific set of skills over the course of the decade, and your firm could fail. A sponge bears risk of attaching near a volcanic vent. Bearing down and pushing toward partnership could be the very best option for you, when considered against the relief of probable paths; but if you do not apply mental rigor to figuring this out, you will have difficulty committing to the decision and, rather than acting out of strength, you may clutch in fear.

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