A Curious Contrarian

For most of my life, I had trouble doing what I was “supposed to.”

It started in grade school … where most other kids memorized the facts, and obeyed the rules.

I didn’t care for rules, and I hated memorizing facts. So I sat in the back, secretly reading books, exploring strange fantasy worlds where crazy things were possible.

But these private sessions were usually interrupted.

Figure it out

Teachers insisted that I prove that I had been keeping up with the official curriculum.

Obviously, I hadn’t. But I was willing to step up to the blackboard and give it a shot.

Trying to reverse engineer math formulas on the fly with everyone watching me was unnerving. And the teachers weren’t exactly supportive.

So I’d invariably be sent to the Principal’s office. I guess the big lesson I learned was that grade school is not a place where they encourage you to figure things out on your own.

When I got to college I majored in Philosophy. This puzzled my friends who deemed this choice to be highly impractical.

To me, it was incredibly practical, but (apparently) not in a way that most people could understand.

Critical Thinking

Studying the great philosophers helped me learn to think more deeply, to go past superficial reflexive assumptions that pervade society.

As Bill Walsh famously observed: “when everyone thinks the same, nobody’s thinking.”

After college, I wasn’t sure where to go next. I just knew that I wanted to avoid mindless superficiality.

Waiting Tables

I spent a few years working as a waiter at an upscale New Orleans restaurant. It was incredibly interesting, and I learned many valuable lessons not taught in school (i.e. how to use psychology to increase the odds of getting a good tip).

But waiting tables didn’t seem like a good long-term career.

So I started thinking about how to get a better job, where (ideally) I’d get paid to think critically. Or, even better, challenge the status quo.

I thought that was what lawyers did, so I applied to law school.

Lawyer Thinking

In law school, professors use the Socratic method to (supposedly) teach students to think critically. This form of learning was challenging and interesting, but once I got into the practice of law…

I once again encountered excessive reverence for tradition and ridiculous resistance to new ideas.

And, there was one idea lawyers seemed especially resistant to…


I was curious about technology. I thought it might improve the way I practiced law. And so I experimented with it.

The lawyers in my big firm weren’t interested in technology. They revered traditions like libraries with lots of expensive books, and billable hour quotas.

I was getting frustrated, but was afraid to leave. After all, what was I supposed to do? Give up my lucrative income and fancy 40th floor office overlooking the Mississippi River? And do what?

Start a solo practice? That seemed completely insane.

But eventually, I trusted this crazy idea. That’s when I finally left the big firm practice.

Going Solo

I started my solo practice in 2006, using technology as much as possible. Fortunately, it turned out well.

I made enough money to be happy but kept my overhead low so my clients were happy too. In short, I could work as much as I wanted, and however I wanted.

The lawyers in my old firm still thought I was crazy. But other lawyers thought my approach made sense.

Some of them asked me to help them adopt technology in their practices. This turned out to be something I enjoyed.

So I kept doing it. The more I did, the more I liked it. And, eventually, I took another leap of faith.

Helping Others

In 2009 I created Law Firm Autopilot and made helping lawyers my full-time mission. A lot of lawyers have said nice things about my work, and the ABA even gave me an award.

In the past two decades, I’ve learned many valuable lessons about using technology, and about teaching people to use it effectively.

When technology works well, it’s magic. But when it doesn’t do what you want it to…

Remain Persistent

A lot of lawyers get frustrated with technology and then feel like it’s impossible to make progress. I know that feeling well (as I’ve described here).

Look, you can figure out everything you need to make your practice run better, including the technology part.

But if you don’t want to figure it out on your own, I’m happy to help.

Sometimes all it takes is just someone to help you believe in yourself more, like this special teacher once did for me.

Want my help?

If so, start by reading my free guide, which explains the basics of paperless automation and affordable outsourcing (i.e. two keys to “working smarter.”)

Book Publications

I’ve  written two books published by the American Bar Association:

I self-published this book to help lawyers better harness the power of PDFs in their law practices:

And I was hired by Nuance to write a book about their PDF software:

Book Me To Speak

If you want me to speak at your event click here to learn about the options for doing so.