Tom Wallerstein

Everyone knows the expression “the grass is always greener on the other side of the fence.” The proverb claims that whatever we don’t have always seems more attractive than what we do have.

If the proverb were true, then we might expect that Biglaw associates would pine to work as solos or in small firm boutiques. But do they really?

It’s no secret that many lawyers are miserable. Some people like Will Meyerhofer have made careers out of trying to reassemble the shattered psyches of victims of Biglaw excesses. But as miserable as an associate’s life might sometimes be, I’ve rarely heard attorneys wistfully musing what it would be like to practice on the other side of the fence, so to speak. Nor do many solo or small firm attorneys often say they wish they worked in Biglaw.

I can’t help but chuckle at the self-rationalizing that seems to overwhelm so many attorneys. Many of them are so cocksure of their career paths and so defensive when challenged, you have to wonder if they doth protest too much. And indeed, although I’m not a shrink, I do have my theories as to why lawyers especially seem prone to criticizing other lawyers whose career paths are different than their own….

Certainly many young attorneys who have the option choose Biglaw for the money. I’ve written before that I think that compensation alone will never sustain a Biglaw career absent an underlying passion for the work. On a more practical level, I’ve also mentioned various advantages I perceive to beginning a career in Biglaw when possible, including the experience, contacts, and pedigree.

I think the real reason most associates who have the option choose Biglaw over small is neither to simply make more money, nor to gain the experience, contacts, and pedigree. Instead, I think most law students hope to enter Biglaw based mostly on what I call cocktail party appeal. That’s just my way of describing the reaction you get from your peers when you tell them in a social setting where you work. When you’re at a 3L mixer, saying you are spending the summer at Cravath rolls off the tongue a lot easier than explaining you will be the sole associate working at the Law Offices of John Smith.

In my experience, once an associate enters Biglaw, all kinds of subtle social pressure makes you want to stay. Biglaw associates are constantly told, and tell themselves, that they are the best of the best, the cream of the crop. They are consistently taught by example to denigrate solo and small firm lawyers. The prevailing attitude among some junior Biglaw associates is that any criticism of the model is the result of jealousy.

Some Biglaw associates assume that the only reason an attorney becomes a solo or joins a small firm out of law school is because he didn’t have any other options. As they become slightly more senior, and the ranks thin, some Biglaw associates assume that those who leave simply couldn’t hack it and only the elite remain.

Lawyers tend to be insecure overachievers, making this group psychology incredibly powerful and enabling young attorneys to rationalize many of the more unpleasant aspects of a job which demands so much of their time, often under unpleasant circumstances.

Solo or small firm lawyers, on the other hand, deal with their insecurities in a different way. Solos enjoy the adoration of being entrepreneurs who work for themselves, and look down on the poor Biglaw associates who are dependent on their work being handed to them. Plaintiffs’-side lawyers often reaffirm to each other, and to themselves, how noble they are for serving the public good. A relatively common attitude of solos and small firm practitioners is to castigate Biglaw associates as mere paper pushers slaving away to the billable hour while sacrificing their morals on the altar of corporate greed.

In moving from Biglaw to boutique, I’ve been privy to all the stories we lawyers like to tell ourselves to justify our choices. Admittedly, at one time or another I’ve told some of them myself.

The “grass is greener” proverb is meant to warn against the danger of romanticizing or exaggerating the benefits of that which we don’t have. Lawyers, however, seem especially immune to that problem. Biglaw associates struggle to rationalize their tough working conditions while solos and smaller firm associates struggle to rationalize the disparity they sometimes suffer in compensation or prestige. It may behoove all of us, whether in Biglaw or boutique, to consider that in some cases the grass may well in fact be greener and that different models offer their own unique upsides as well as downsides.


Tom Wallerstein lives in San Francisco and is a partner with Colt Wallerstein LLP, a Silicon Valley litigation boutique. The firm’s practice focuses on high tech trade secret, employment, and general complex-commercial litigation. He can be reached at [email protected].


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