Quitting

There’s an episode of the show Friends that I always think of whenever the topic of quitting arises. Rachel Green and Joey Tribiani are in a sailboat in one of the rivers off of Manhattan and Rachel, who learned to sail as a kid at the hands of her overbearing father, is trying to teach Joey to sail.

After a little while in the boat, Rachel starts channeling her father’s crushing authoritarianism. Joey, who is not having nearly the amount of fun he expected to have learning to sail, announces, “I quit.” 

Rachel quickly shouts back, an exact echo of a speech made by her father, “Greens don’t quit!” Joey defiantly yells in retort, “I’m a Tribiani and Tribianis quit! 

Quitting gets a bad rap.

One of the first things we learn about quitting comes from the pithy saying, “a winner never quits and a quitter never wins”. The baked-in censure being all too obvious to even a child, that quitting anything at any time for any reason makes you a loser.

This is a pretty unfair frame through which to interpret quitting. Quitting (or quiet quitting or strategic semi-retiring or whatever other phrase we are now supposed to use) can be a useful tool. If you’re driving in the wrong direction, for example (an unfortunately non-hypothetical one, since not even Google Maps can cure me of confidently going in the direction of my dreams, if not my intended destination) quitting is a really solid plan. If you are ahead at the blackjack table in Vegas, as I briefly was this past winter, quitting would have been a grand idea. He says in hindsight. 

And quitting has its place in law practice, too.

Part of the reason we hate quitting – apart from feeling like a “loser” – is because the act of quitting is a tacit indictment of our earlier decision-making process. Or in other words, because we made a mistake, to use the parlance of our time. And there is just not much on this earth that lawyers hate more than making mistakes. 

We’re not a profession of light-hearted Doris Days sanguinely accepting the winds of fate. We go to the mats trying to never make a mistake and we take it hard when we do make one. Not to mention that in several practice areas we have colleagues at bar on the other side of our matters who have the solemn duty to exploit the mistakes we make.

So, yeah. Mistakes for lawyers are no bueno. And quitting is evidence of a mistake. And therefore quitting is bad. 

Here’s the thing though: quitting isn’t always evidence of a past mistake. Sometimes the facts on the ground change and what was a good decision at the time it was made needs re-examination. And even if the earlier decision was a mistake, not all mistakes are unrecoverable. Not every blow is a dolorous stroke. People survive a lot of stuff.

Maybe it’s time to normalize quitting. To get us started, here are seven times in law practice where quitting might be the best decision:

1. Changing practice area: law school, at least my law school, did a woeful job of helping law students figure out what kind of law they want to practice. My wife (who I met in law school) has had a great career as an in-house lawyer. Unfortunately, she thought she wanted to be a litigator and never took a single useful class in law school for what ended up being her career trajectory. Sometimes you try something and it just isn’t a fit. If you’re practice area isn’t what you had in mind, maybe making that switch should be on your radar screen.
2. Changing firms: law firms always remind me of Anna Karenina. “All happy families are alike; each unhappy family is unhappy in its own way.” Law firms are strange businesses, heavily dominated by a culture and set of personalities that is at once familiar but also deeply individual and idiosyncratic across organizations. A firm may look like a perfect fit on paper, but the lived reality of practicing there may be decidedly different. If your firm is not a fit, quitting and finding another one is not the worst idea.
3. Changing geography: over time, the fates of cities, towns and states ebb and flow. You may have put down roots in a place that has through no fault of your own made it very hard to thrive. I’ve gotten to know lawyers and their practices all over the country, and one thing I can say for certain is that while practicing law is a uniformly tough job, there are places where it is a lot easier to be commercially successful. The old saying, “a rising tide floats all boats” isn’t wrong.
4. Changing partnerships: this one is hard because it feels so personal. But sometimes, you start a new firm with a partner who is a close colleague maybe even a great friend. And you are just sure that the frisson that makes that friendship work is going to make for a dynamic and enriching partnership. And… it just doesn’t. Partnerships are different than friendships and are a lot more like marriages. And we all know the success rates on those unions. Sometimes, “let’s just be friends” applies to law firms, too.
5. Changing up marketing efforts: I’m heavy on the old sayings today, but this one puts me in mind of another old saw, “what got you here won’t get you there.” That is meant to mean, if you want to keep getting better and progressing, you can’t just keep doing the same old thing. You need to level up. Nowhere is this more true than in law firm marketing. Over time, you may find that some of your old tried and true marketing efforts aren’t paying the dividends they used to, whether that is bar association participation or running Google ad campaigns. Things change and we need to know when to quit and try something new.
6. Moving on from technology expenses: this pains me to have to write, because I spent so much of my time over the past many years trying to get lawyers to make friends with technology. But sometimes technology expenses (investments, they would like us to say) don’t pan out. Software companies merge or go under, products get bloated to unusability or neglected altogether. Or some sea change comes along, like moving from servers to the cloud and some products don’t survive. (AI is likely to be the next such sea change… you know I had to tuck some AI reference in here somewhere…) Having sunk an enormous amount of time and money into a given technology doesn’t mean that you should stick with it past its expiration date.
7. Quitting on some clients: I saved this one for last because it is the one that nearly every lawyer can agree on. Some clients should be fired. Or you should quit representing them. Whichever formulation works in your head. There’s not much that nearly every lawyer agrees with, but this one comes close. Quitting those clients – you know which ones they are – is almost never a bad call.

I hope that list has given you some pause on thinking about the role of quitting in your practice. It doesn’t make you a loser and it doesn’t have to be indicative of a mistake or failure. Sometimes, quitting something just makes you sensible and smart. Two pretty good traits for a lawyer.

To close, I will refer you to the eternal anthem on quitting: 

You’ve got to know when to hold ‘em
Know when to fold ‘em
Know when to walk away
And know when to run