I didn’t grow up wanting to be a lawyer.  Most of what I heard about lawyers when I was younger was from lawyer jokes.  Then, I took a Contract Law class when I was in business school at the University of South Carolina. I was…

I didn’t grow up wanting to be a lawyer. 

Most of what I heard about lawyers when I was younger was from lawyer jokes. 

Then, I took a Contract Law class when I was in business school at the University of South Carolina. I was about 20.

That Contract Law class was taught by a self-described “old country lawyer” from nearby Calhoun County. He was performative, spoke slowly with a pronounced drawl, and was full of folksy Southern charm. 

He rose to prominence in his rural community by helping his fellow countryfolk solve their problems. He wasn’t a specialist at first: he drafted Wills, set up trusts, settled disputes, and litigated small civil cases. 

Eventually, he drifted towards what interested him most: business. He ended up representing several large farming companies in his area and built up a law practice. 

He decided to do some teaching in the twilight of his career, which is where our paths crossed.

On the first day of class, he started by talking about how his career path required him to be a self-learner.

Self-learners are naturally curious – people able to apply new ideas and concepts quickly. A pretty handy skill for a lawyer. I suppose everyone can be taught to be a self-learner – and there are certainly habits that help form the skill. But some are more naturally suited for it than others, like the “old country lawyer”.

He talked about the process of being able to learn a new piece of information, array it against a framework of legal knowledge in your mind, and then fire back with the right question or advice. He was describing an everflowing process for acquiring knowledge, with a framework – a legal framework. 

The best lawyers are lifelong students, always processing info and adding to their knowledge base.

I recognized that same trait in myself, when I met that “old country lawyer”.

I watched him diagram the various aspects of business law on the whiteboard that summer, and the concepts clicked for me immediately. I easily understood what he was talking about without much effort – usually after hearing him describe things only once. It all made sense to me, naturally. I felt this light bulb go off inside – “ping”.

That’s why I became a lawyer – I followed that “ping” feeling. 

I had already decided to seek more education after undergrad, but I didn’t want to get an MBA. I wanted something more practical – a skillset, a trade. I wanted what the “old country lawyer” had, so off I went to law school.

Only then did I grasp just how vast the legal profession is – all of the different forms of practicing law. It’s like an amoeba, touching all areas of society.

Family or personal matter? Check, lawyers are involved. Business or money matter? Check, lawyers there, too. Property issue? Check. Natural & environmental concerns? Check. Government and politics? Double check.

I started seeing the world through the lens of the law, imagining myself as a practitioner in all of these different ways.

Like the “old country lawyer”, I followed my natural drift. I followed that ‘ping’ that lit me up when I learned about contract law. That ‘ping’ led me to study the subjects I found interesting: business/finance, technology, human systems, intellectual property, international transactions, investing. And those studies, and then years and years of repetition as a practitioner, led me to have the law practice I have today.

Today, I’m fortunate enough to help my clients solve problems that I already enjoy solving. The stuff in my wheelhouse never gets boring for me. I’m the lifelong student type for my preferred subjects, so the knowledge compounds.

And that’s a big part of what being a lawyer means to me – the opportunity to help others by providing knowledge, judgment and strategy. I chose the business/finance law arena since it’s the game I enjoy playing the most. 

But when I look around, the legal profession looks worn down – and sometimes sleazy. I don’t like it. 

It seems like every billboard on every major highway in America is an advertisement for personal injury lawyers. 1-800-LETS-SUE in bold glossy font, screaming at me. (I don’t have anything against PI lawyers and actually think they serve a great function in some cases. But when the legal pursuit itself becomes too much of a commercial enterprise, I’m not sure that we’re all better off… anyway, I digress.)

So I try to remember the “old country lawyer” and focus on other lawyers that I admire. There are plenty. I often stumble upon these ‘recovering lawyer’ types who found a second act, typically landing in business, investing, writing or politics. I’ve made a list over the years.

Charlie Munger is at the top of my list. He had a brief legal career: he graduated Harvard Law School in two years (instead of the typical three), spent some time as a law clerk, and practiced general/business law for several years before going into investing.

The business world is full of other examples: Sam Zell (real estate tycoon, went to law school), Brad Gerstner (investor, former M&A lawyer), Herb Kelleher (corporate lawyer, founded Southwest Airlines), Bruce Karsh (corporate lawyer, co-founded Oaktree Capital Management), and numerous others.

And then there are lawyers who used the law to shift history and grind the gears of human progress. These lawyers are higher up the totem pole, morally speaking. They make the rest of us look like paper pushers. 

People like:

Nelson Mandela – started South Africa’s first black law firm, often helping fellow black citizens fight against apartheid discriminatory policies in the courts, served decades in prison for his activism and was eventually freed to become the first democratically elected President of South Africa.

Mahatma Ghandi – also worked as a civil rights attorney in South Africa before later returning to India and catalyzing the movement for independence from British colonial rule.

Thurgood Marshall – quickly recognized the power of using the law as a tool for social justice – one of his first cases was suing the University of Maryland law school for previously denying him admission (he ended up at Howard) – and was the first black Supreme Court Justice in the United States.

Ruth Bader Ginsburg – struggled to find a job as a female lawyer in the 60s, which led to her legal work as an advocate for women’s rights, and also ended up on the Supreme Court.

James Baker – worked for many years as a corporate lawyer before getting into politics & government, and later served as White House Chief of Staff and eventually Secretary of State, using his formidable skills as our nation’s top diplomat.

There are many many others.

So when I hear all the lawyer jokes, I smile. I get it. I understand why people have become frustrated with lawyers. I recognize that a lot of people see the lawyers on America’s billboards as the ‘main character’ of the profession – it’s our loudest archetype. 

I’m just sad that more people don’t meet lawyers like that “old country lawyer” who jazzed me up about Contract Law back when I was just a pup.

I choose to think about the lawyers who pushed things forward, who blazed their own trail. I try to emulate the ones, like Charlie Munger, who used their legal knowledge & training to develop a code of ethics for their own life and business. That’s my camp.

Using the law to change the world, first by changing myself.

No one can be happy until they’ve forgiven their parents. –Konstantin Kisin

No one can be happy until they’ve forgiven their parents.

–Konstantin Kisin

God is not on the side of the big arsenals, but on the side of those who shoot best. –Voltaire

God is not on the side of the big arsenals, but on the side of those who shoot best.

–Voltaire

Every prophet has to come from Civilization, but every prophet has to go into the wilderness. He must have a strong impression of a complex society and all that is has to give, and then must serve periods of isolation and meditation. That is the…

Every prophet has to come from Civilization, but every prophet has to go into the wilderness. He must have a strong impression of a complex society and all that is has to give, and then must serve periods of isolation and meditation. That is the process by which psychic dynamite is made.

–Winston Churchill

Building a business is like climbing a mountain. The journey of life, the same. Your trail winds around, up and down over ridge lines, through the valleys.  There are overlooks where you stop and view where you came from, and where you’re going. There are…

Building a business is like climbing a mountain. The journey of life, the same.

Your trail winds around, up and down over ridge lines, through the valleys. 

There are overlooks where you stop and view where you came from, and where you’re going.

There are markers along the way, helping keep you on track. 

You come to forks in the trail, forcing you to choose your next direction.

There’s also crappy weather sometimes, even when you don’t have the right gear. Your boots get soggy, and you feel cold and wet.

And sometimes there are perfectly clear nights where you camp under the stars and, even without amenities, find yourself grateful for the journey. 

But the most important part of the climb, by far, is who you take with you.

There are co-hikers and fellow travelers, but those come and go. You hike together for certain stretches of trail, and then they split off on a different path. 

You are the only one who walks your own unique trail from start to finish.

But you are not alone. Or, at least, you don’t have to be. For a really successful climb, every hiker needs a trail team.

Your Trail Team is your brain trust. Your council of personal guides. On the trail, they’re with you all the time in spirit – always just a satellite phone call away. Some days, they meet you on the trail for those tough soggy weather slogs and hike alongside to keep you motivated. And when you reach a new milestone, they’re there to celebrate your progress.

Your trail team keeps you safe, and sane, along the journey.

So who is this trail team? 

Scientists

First, you need scientists.

Your scientists do your measuring for you. How long you have to go to reach the summit. How far you’ve come. What new gear you need, and what old gear you can get rid of. 

They keep you lean and stealth. They keep your heart rate monitor finely-tuned.

Your scientists are your three-headed monster: bookkeeper, CFO and CPA.

These days, there are a lot of ‘fractional’ scientists, who helicopter in but aren’t full-time. And that’s perfectly fine, as long as they’re there when you need them.

Guard

Second, you need a guard. 

Your guard holds your funds and makes sure they’re kept safe. He knows the lending landscape in case you need to borrow, and works with your scientists to make sure you’re healthy enough to do so.

Your guard is your banker. Your banker provides security. 

Some guards also serve the function of wealth manager, giving you advice on how to invest your excess funds. 

The more complicated your journey becomes, the more support you will need from your guard.

Scout

Third, you need a scout. 

Your scout provides your eyes and ears on the trail. They hike with you the whole way. 

Your scout is your chief of staff. 

And while they have other responsibilities to keep you on track, every once in a while you send them off trail to survey the landscape and bring back information. 

It’s important for your scout to have access to the rest of your trail team in case of emergencies.

Sherpa

And finally, every mountain climb needs a sherpa. 

They’re always there in the background, watching your progress. You share your GPS location with your sherpa so they can always see where you are, even from afar.

Your sherpa is your lawyer. 

Your sherpa helps you decide which forks in the road to take, and which to avoid. They help you make clear decisions on those cold crappy weather days when you’re feeling emotional. 

And they help you choose your next mountain once you’ve summited the last.

If you are distressed by anything external, the pain is not due to the thing itself but to your estimate of it. And this you have the power to revoke at any moment. –Marcus Aurelius

If you are distressed by anything external, the pain is not due to the thing itself but to your estimate of it. And this you have the power to revoke at any moment.

–Marcus Aurelius