Want to Ensure Solo Success? Obsess Yourself.

Updated August 31, 2022

Don’t Express Yourself – Obsess Yourself!

Over the past few years, passionate has been one of the most overused modifiers of
entrepreneurs and startups. If you don’t believe me, check out LinkedIn, where “passionate”
turns up as a term in 5,447,000 profiles. Increasingly, solo and small firm lawyers also use
the term to describe themselves. And while I’ve celebrated the importance of passion in
practice myself, increasingly, I’m realizing that while passion can make law practice more
enjoyable, it isn’t necessarily key to solo and small firm success. Obsession is.

As those of us who’ve been in practice (or marriage!) for ages realize, the problem with
passion is that while it’s thrilling at those early stages of infatuation, it inevitably wanes. If
you’re lucky, you may be able to re-light that fire but I’m not sure that it ever burns as
brightly as in the beginning. And when passion dims or worse, dies – so too does the
enterprise – be it a law firm or a marriage – that it once fueled.

Obsession is different. And while it’s not necessarily a trait you’d want in a partner, it’s the
secret to successful solo and start-up lawyers. Solos obsessed with a practice area eat,
sleep and breathe it 24-7. Obsessed solos immerse themselves in the minutia of a practice
area, single-mindedly tracking every new development (and often reporting on it in a blog or
newsletter), consuming every possible complaint or contract clause in search of new tricks
and attending as many bootcamps and CLEs and seminars as they can afford to in
relentless pursuit of mastery. Moreover, obsessed solos don’t hold themselves at arms-
length — they dive right into the fray and get their hands dirty. If they represent a particular
demographic, like single moms or tech startups or racehorse owners, you’ll find them on
every list-serve and at every meet-up or association event, trying to gain a better
understanding of the challenges their clients face or sharing resources and advice.

There are dozens of examples of obsessed solos online – from Tom Goldstein – an oft-
cited example of a lawyer obsessed with the Supreme Court, or Howard Bashman who for
more than a decade has been hunting down and reporting appellate news at his blog, How
Appealing. That’s no coincidence either, since obsessed lawyers are great bloggers – not to
mention that lawyers obsessed with the art and science of blogging like my buddy Kevin
O’Keefe build successful blogging companies. Obsession is so powerful that it can grow an
enterprise that serves a need that you didn’t even realize existed. Look at former Above the
Law editor, David Lat, who converted his obsession with big law gossip into one of the
today’s most popular legal news sources.

Obsession itself isn’t difficult – to the contrary, it’s easy. That’s because when you’re
obsessed with a subject matter, working on it 24/7 is pure pleasure; so much so that you’d
almost do it for free. And when you’re obsessed, you want to share that obsession with
others, so selling what you do or finding clients comes naturally.

What is hard, however, is finding that object of obsession, the thing that so captivates you
that you want to do a jig. Obsession may have a personality component as well – I suspect
that some of us (myself included) for whatever reason simply don’t have it in our DNA to
embrace something with the unrequited, single-mindedness that obsession demands. But if
you’re looking for one of the keys to succeeding in solo practice, instead of hiring coaches
or investing in marketing or SEO, figure out how to obsess yourself. Because more than
anything else, obsession will make you truly unstoppable.