Smaller Law 101: Advice on Growing your next Law Firm

Exactly three years ago, I was struggling with two decisions. One, whether to buy a boat. Two, whether to leave my long-time law firm.

As to the boat, the world is full of advice about that. Ask anybody you know, and you’ll instantly hear the joke about the “two best days of a boat-owner’s life.” There’s so much information online (generally negative) that a prospective boat buyer has to actively ignore it all.

As to the second (far more important) decision, I was surprised by how little information was out there. Bar associations tend to avoid the topic like the plague. Their business model is to keep big law firms happy, or, at the very least, to not encourage mutinies. Other lawyers aren’t much help either–you’ll rarely get an honest response. They’ll either embellish (for good or bad) or, worse, let slip to somebody that you’re thinking of leaving.

As a result, most lawyers keep quiet and rely on legal recruiters or their own ego, two very unreliable and heavily biased voices.

In this wild Nashville legal market where lawyers are constantly switching firms (and, in a surprise twist, switching back to the original firm), there’s value in real talk. Sometimes the billable hours aren’t greener at the other firm.

For me, I got the law firm decision right. Having said that, even though I’ve had three very successful years, it’s all been built on a foundation of small mistakes, miscalculations, and lessons learned the hard way.

I could write a book about all the things I’ve learned about entrepreneurship, law firm management, marketing, and psychology but, instead, I’ll write some blog posts here over the next few months as the 3 year firm-iversary approaches.

As for the boat? I totally screwed up that one, a mistake so notable that it was documented on the front page of USA Today.

If you’re considering leaving your existing firm, I hope that these blog posts over the coming weeks will be useful –or maybe just keep you out of the national news.

Small Law Firm Life: The Best, The Worst, and All at the Same Time

Three Sundays ago, I got locked out of my laptop.

Neither Dell, Microsoft Support, or frantic prayers could save the day. My working laptop was somehow connected to an expired domain (my expired firm), and it was locked shut. (“A very expensive door-stop,” the nice lady at Dell Support in Texas unambiguously explained.)

After spending 5-6 desperate hours on the phone on a gorgeous early-fall day, I had cobbled together the diagnosis: This is exactly what the system is supposed to do in a situation like this; and The remedy was to wipe the computer and start fresh.

This was bad news.


If you’ve ever sat next to me at an event or at a cocktail hour, you know I like to talk in colloquialisms. For me, it’s a way to survive small talk, but also a way to be authentic and also contextually appropriate (i.e. to make a joke).

Maybe the best response from me would be a simple “I’m fine, how are you?” But, sometimes, why not be honest and funny (especially if you are one of the rare Nashville attorneys who has won a city-wide award for their sense of humor)?

If done well, the response is short, funny, but also brutally (and subtly) honest.


While doing the rounds on the 2021 lawyer holiday party circuit, lots of people asked if I liked my small law practice. My response was generally the same: “It’s the best job on earth, and it’s also the worst job on earth. But never in the middle. Sometimes, I miss the middle.”

It was quick, easy, and honest. For more than a decade, at somebody else’s firm, I spent a lot of years in the middle. I billed my hours and won my cases, but I didn’t have any say in the big (or the day-to-day) firm issues. It was frustrating and unfulfilling, but also comfortable and familiar and easy.

Plus, on any day when my computer didn’t work, I had somebody to call who spent their Sunday figuring it out.

In fact, that’s something I told the Tennessee Bar Association’s Sidebar Podcast last year: “My job used to be to show up, do awesome legal work, and write down my time. Now, my job is to do all that, and also take out the garbage.”


Back to the laptop. In the end, let’s be clear: It all got sorted out.

My legal tech “committee of one” had made the right choices about Clio (a cloud based practice management system), NetDocuments (cloud based documents), and a redundant Microsoft OneDrive backup. Plus, I have a backup computer (“Dynamite”) that is fully functional and has been promoted to first chair.

Other than the hassle, wasted time, and the year of my life that the stress cost me, all ended fine.


Last year, after using my “best job, worst job” line at a holiday party, I got a text the next day, from a managing partner at a local Big Law Firm who I had talked to. Maybe I wanted to interview with them and cut out all the hassle of running my own thing, he asked.

All he had heard was the “worst” part, I guess. It was awkward and awful responding (and I made sure to avoid him at the next holiday party), but I had to be honest: “Hey, thanks and I may take you up on that someday, but I’ve had a long stretch where it’s been the ‘best job’ and I’m going to ride this for a while.”

There’s not really a point here, other than to say that you should be sure to back up your documents in multiple places. And, also, that life is too short to live in the middle. And, finally, not to be too braggy, but small law firm life really is the best.