SmallLaw Vacation Policies


While the rest of you have spent the past three weeks sipping eggnog and draining champagne flutes, I’ve been on a mountain in Argentina — and it’s not because I needed some alone time after finally reading the comments to my posts. I’m down here trying to get to the top of said mountain, and the acclimatization process drags out the journey considerably. It’s been a lot of reading and bonding with fellow climbers.

This is my second attempt to bag this peak. The first time, not only did I not make it to the top, I didn’t even make it out of the office. Turns out Biglaw is not very vacation-friendly. (Who knew?!) An associate could give notice five years ahead of time and it wouldn’t matter, a partner could tell him the day before the trip that he can’t go. And no, in my case it wasn’t the day before, but rather a month or so before. Still close enough that I lost a four-figure deposit, but I appreciated that the partners felt bad about making me cancel the trip, though they were careful to hide their grief. (So careful they never batted an eye.)

The good side of being in SmallLaw: no one to veto my vacation.

The bad side of being in SmallLaw: no vacation pay! As far as I know, there have been no direct deposits to my account while I’ve been here. (Now I’m thinking maybe I should have crowdfunded this trip.) And though two out of the three books I brought are legal texts, my clients know I’m on a mountain, so any time I bill down here — or rather up here — is going to be scrutinized heavily. And they’d probably expect a percentage discount given that I’m functioning in thin air.

That’s the trade-off. You get to make up your own vacation policy, but the double-whammy of no billing yet having to continue to pay your overhead expenses limits how many breaks you can take. Not to mention the headache of having to arrange coverage for your clients. Of course, you have to do this in Biglaw as well, but there are more moving parts in SmallLaw since the people covering for you are running their own firms, and billing procedures can vary wildly from client to client, much less solo practice to solo practice.

Still, it’s pretty awesome not to have to ask permission from someone. Feels more adult. It’s times like this I can’t imagine going back.

Originally, I had thought I’d be writing a post drawing an analogy between mountaineering and sustaining a SmallLaw practice. While there was a comparison to using a wag bag I was particularly proud of, I couldn’t figure out what is analogous to the summit. I don’t know yet if there’s a point in building a practice in which it feels like you’re at a peak and it’s all downhill from there. Perhaps one of the SmallLaw veterans out there can enlighten me?

Note: I would like to send a special shout-out to Josh Harris of Alpine Ascents, who had an outsized contribution to my summit of Aconcagua. Thanks Josh!!