Biglaw, Boutique Law Firms, Small Law Firms, Travel / Vacation

From Biglaw to Boutique: Reflections from Cayman

Tom Wallerstein

I recently had a client ask me about asset protection strategies. Having read The Firm (affiliate link) before I ever went to law school, and mindful of the classic Tom Cruise movie of the same name, of course I did what any diligent attorney devoted to client-service would do: I headed off to the Cayman Islands to investigate.

Due to an unfortunate series of strange boating accidents which I am not at liberty to discuss, my trip ended up lasting a bit longer than I expected. My email and telephone conversations also became compromised, hence my extended ATL hiatus.

Alas, the good guys prevailed, I am back safe and sound, and I’m happy to write about some of my reflections from beautiful Cayman (pronounced, as I learned from the locals, “Cay-Man,” with two distinct, equally prominent syllables, almost rhyming with “Cave-Man;” not “Cay-min” rhyming with “layman”)….

I spent much of my non-working time snorkeling in the Caribbean Sea. For me, snorkeling can be simultaneously both relaxing yet exhilarating. I saw giant sea turtles, starfish, kaleidoscopic coral reefs, hundreds of species of fish, and even snorkeled in “stingray city,” where dozens of stingrays have become so accustomed to snorkelers that they only rarely decide to sting and kill them. (As far as I know, they don’t extend the same professional courtesy to lawyers as do sharks).

Snorkeling can be a transcendent experience. Sometimes the sea is still as glass and yet, right below the surface, you can see a vast, colorful, breathtaking world. It is easy, particularly for lawyers, to believe that we have all the answers. But snorkeling reminds me how imperfect our knowledge really is, and that sometimes we can see an entirely different world if we simply change our perspective (in this case, turning your head down, into the water, with the help of a mask and snorkel).

Remembering our inevitable myopia, the lesson for lawyers is to be humble, not arrogant; modest, not smug. All of us have more to learn and new ideas to try. These are especially poignant lessons for attorneys forming their own solo or small-firm practices. You might be tempted, for example, to stick with the practice areas in which you have experience. And indeed it makes sense to build your practice around what you already know. But you also have to be willing to embrace new skills — there’s probably a practice guide for it — and always consider new practice areas, marketing techniques, billing methods, etc.

Even attorneys who have been in solo or small firms for many years would be wise to stay open to new ideas. Many attorneys starting their own firms have learned that adopting new technologies can result in cost savings that allow them to be economically viable. Conversely, clinging to only what is familiar, and refusing to stray from the traditional, can sound the death knell for firms big or small. Some have identified resistance to change and refusal to adopt new approaches as the primary reasons for the collapse of Dewey & LeBoeuf, for example.

Solo and small-firm attorneys have much to gain from being humble. Attorneys in smaller shops are more likely to be dependent on other attorneys for referrals. Smaller firm attorneys also are more likely to need to call upon others outside their firm to help or advise with regard to particular issues. It pays to remember that different perspectives can lead to valuable insights that you might overlook, just as we might overlook what lies beneath the calm face of the sea.

Not being too proud to ask for help is essential for anyone trying to build a practice. When I started my firm, I was pleasantly surprised by the number of lawyers who were willing to go out of their way to offer their guidance and advice. Biglaw expats, I have found, are especially eager to help others when they try to break away from Biglaw to do their own thing. You need to become comfortable not only with asking for help, but also with finding opportunities to offer help to others.

Snorkeling also reminds you that, quite literally, there are plenty of fish in the sea. The aphorism rings true not only for ATL Courtship Connections, but also for small-firm attorneys trying to build a practice. Devoting significant time and energy for a pitch can be quite costly, in many ways, and rejection can be devastating. But you have to remember that potential clients abound and not to become discouraged by temporary setbacks. And, of course, remembering the multitude of fish should also help you remember that you need not eschew your fellow fishermen.

* * *

Just as I encountered entirely new worlds by snorkeling in the Caribbean, so, too, did I encounter an entirely new world when I left Biglaw to form a litigation boutique. I learned that truly excellent lawyers practice in a variety of contexts and that there are as many different ways to be a lawyer as there are fish in the sea.

It’s tough to run your own business, even if doing so while living in one of the world’s greatest cities and habitually eating some of the world’s most varied and delicious food. And woe is me for declining another vacation, instead spending my time slaving away in Grand Cayman. It was a tough gig, but somebody had to do it. Fortunately I learned a lesson or two that I hope will have enduring value for my practice.

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

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