When I was in Biglaw, I got to know a few people at the investment banks that were our primary clients, folks who were at the same spot on the bank totem pole as I was on the firm totem pole. I think I met a few of them in person, mostly because one of the banks shared our building, but for the most part they were voices on the phone. There were certainly several I became comfortable working with and we would indeed occasionally discuss non-work items like the merits of Roger Clemens’s legal team vis-à-vis Barry Bonds’s team. Still, calling these folks “friends” might be stretching it a bit. So I can’t really say that back then I had friends as clients, other than a couple of friends who I took on as pro bono clients.

But in SmallLaw I do have friends as clients. Looking back, it’s almost predestined it would turn out that way, since the email telling people I was open for business went out to friends and family, so my first few clients were always going to be friends. (Family members were never going to be clients, since my family is tiny and for the most part don’t have legal issues. Plus they still think “self-employed” is synonymous with “unemployed.”) I guess a part of me had assumed there were all these people who were clamoring for legal services who my friends could easily send my way. But no, what actually happened was my friends themselves engaged me to provide legal services. For money!

So what’s it like having clients who were friends first, and in some cases friends for a long time? It could have been a problem had I been spending the last few years acting like Mr. Legal Titan at parties and happy hours — which I’m sure would have made for pleasant company — but fortunately the Biglaw work was pretty boring, so I never really talked about it much, and certainly never misled anyone as to the type of work I did. Then once I went on my own, my friends just asked me if I could handle certain matters, though often I would have to complete the pitch to a CEO or major shareholder or whoever would be okaying the checks.

Some people don’t like to mix business and pleasure, preferring their work life to be in one silo and social life to be in another silo. That’s hard to do when you have friends as clients, and I think in general it’s hard to do when you only eat what you kill, as opposed to the Biglaw force-feeding. Frankly, these days I’m not even sure where business ends and social life begins. If I go to a Nationals or a Yankees game with a potential client, is that really work? Maybe this one time, when I took a contact I had just met at a networking event the prior week to a baseball game and found out after the second inning — when we had finished talking about work — that we had nothing in common. We spent the rest of the game in silence. Awkward.

What’s nice is I do have the opportunity to talk to my friends more, and we’ll know if the other person is busy by how much time we talk about non-work items. If it’s a straight business call and that’s it, at least one of us is busy. If we spend 20 minutes of the call talking about what color a dress was, maybe not so much.

But it can be harder to tell a friend I screwed up. For any client, if it’s a real error, a phone call is mandatory. The last time I had a situation that warranted a phone call, I felt like I was back in high school, trying to work up the courage to ask out a girl. I kept staring at the phone, hoping it would make the call for me, sua sponte. But tough calls can also deepen the client relationship, assuming a screw-up didn’t bring a friend’s business crashing into the ground.

And now that I have my own practice, few clients are merely disembodied voices on the phone. Even the people who get referred to me and sign the engagement letter and pay me without meeting me I’ll try to meet in person at some point, if only to strengthen the bond so they’ll use me again when another legal matter comes up, instead of going back to the referral source for another referral. And who knows, if we click, we may become friends and start going to baseball games.