Creative Lawyering

Ever since I started telling people I was giving up the ad game for law school, I’ve gotten variations on the same question: Why would I leave the hip, happening, and creative world of advertising for the dour drudgery of law? Recently, a lawyer from one of the firms that I interviewed with for a summer job asked me that. Which doesn’t bode especially well. I mean, it’s one thing for people outside both industries to assume that advertising is sexy and law is dowdy. But this guy kind of confirmed the latter, right?

Anyway, I’ve started to develop a theory: a good lawyer needs to do just as much—if not more—creative thinking as any Madison Avenue soap huckster. First, though, you have to accept the premise that, as Jack Foster put it in How to Get Ideas, “An idea is nothing more or less than a new combination of old elements.” Actually, I think he borrowed that from an even older book on idea generation, by an author whose name escapes me at the moment. But that’s the whole upshot: Creative thinking is really the process of making connections and associations—recognizing how otherwise disparate things go together to make something special.

This has probably never been more true than in our post-modern, meta-savvy culture where everything is a reference to an association with some other in-joke from 15 minutes ago.

Still, the only way to make those connections is by being receptive to possibilities that aren’t obvious. And a willingness to actively wonder “What if . . . ?” It occurred to me while I was doing a fairly fundamental research and writing exercise that maybe this ability is part of what separates the effective lawyers from the also-rans.

Here’s the thing. My performance on fall exams didn't exactly blow the top off the curve. I did fine with multiple choice and short answer, but I kind of crashed and burned on longer essays where I had to identify and sort out multiple issues and apply the appropriate rules. And as any 1L from north of the mean will tell you, there’s more than one way to skin a tortfeasor. You have to be able to see and explain all the ways the rules might apply to a given set of facts, not just the most obvious one.

Back when I was a no-talent ass-clown copywriter aspiring to be a pretty good copywriter, I went to Tom Monahan’s Ad Hell Camp. One of the things I learned was: Don’t stop at the first good idea you have. Keep going. Keep asking “what if . . . ” until you have a dozen ideas that might be something. But what you should never do is delude yourself that your first decent idea is enough, because chances are, it's a fairly obvious one that pretty much anybody could come up with.

This, it seems, is the very thing that hobbled my exam performance. And the reason I'm likely, as Al Franken/Stuart Smalley would say, to die homeless, penniless and twenty pounds overweight. I have a tendency to be what we in the law biz call “conclusory.” In other words, once I see a solution, (particularly under the fairly intense time pressure of an exam) I stop thinking about other possibilities. This is bad in advertising, but it can be fatal for a lawyer. In advertising, assuming you operate at fairly high level of conceptual sophistication to begin with, your one good idea might turn out to be the best solution and get you fame and awards and a coterie of nubile co-ed interns. And if not, no harm done; it’s probably still a serviceable solution and it moves the needle* for your brand. But for a lawyer to focus on just that one idea, he’s leaving himself (and his client) vulnerable to the other side by not seeing other ways an issue can be argued or the facts construed, not seeing how the other side can defend against his idea. I'm sure there are other possible permutations of prospective doom, but I'm too tired to think them all through just now.

Now, I know, by and large, that lawyers can't bill for "concepting" time. And I imagine that a good amount of legal work is fairly straightforward application of rules to facts. But I think there's something to the notion that writing ads and writing briefs—done properly—is more alike than different. And if anything, creative thinking—at least the kind that exhausts all possible approaches and solutions—is actually more essential to a lawyer than a so-called “creative.” At least that's my hope.

*Another idea appropriated from Mr. Monahan.