When I was in prison, I wanted to be a better reader. But early on, when I told Michael Santos I’d read a book, he didn’t say, “Good job.” He asked, “Why did you read it? What did it teach you? How will it help you now? How will it help you later?”
I couldn’t answer well. So he gave me a strategy: take notes, write about what you’re learning, and share it with your network.
That’s what I started doing. And I kept doing it after I came home, though it got harder. I had a business to build, talks to give, people depending on me. Still, I tried to keep reading and writing the same way.
One book has followed me for more than a decade:
How to Live: A Life of Montaigne in One Question and Twenty Attempts at an Answer, by Sarah Bakewell.
A professor at NYU gave it to me in 2011, after a lecture. I’ve returned to it often, and I’ve shared it with more than a hundred people in our community. I only know three who’ve actually read it.
Bakewell builds the book around a single question:
How should one live?
Montaigne didn’t answer it once. He answered it twenty different ways. Each one is personal, inconsistent, and based on his lived experience. Here are some of the questions she organizes the book around:
- Should you live openly?
- Should you pay attention to what you’re thinking?
- Should you take responsibility for what you justified?
- Should you stop fearing what hasn’t happened yet?
- Has your perspective changed?
- Should you write to understand or to impress?
- What are you avoiding?
These are questions that matter if you’re under investigation, preparing for sentencing, or trying to make sense of what went wrong.
Montaigne wrote about everything. He admitted to slapping a servant. He talked about lying to his wife, mocking people he respected, claiming he had conquered his fear of death, then panicked when his horse threw him. He never tried to seem consistent. That’s part of what drew me to him. That, and his obsession with death, which is something I have always thought a lot about. It is the primary reason I started reading the book.
His father died of the plague. He almost died himself. This was 500 years ago. People were dropping dead around him for all kinds of reasons. He was terrified of death.
When he lost his best friend (who got hit in the head with something like a tennis ball and died from a brain hemorrhage), he retreated to his tower. He couldn’t move for weeks. He just sat in grief. That’s what I did when I was indicted. My version of a tower was my “man cave” in Studio City, CA. I sat on a couch. Some days I didn’t move. I stared at the wall or left the TV on. I was so afraid of prison, of what the rest of my life would look like, that I couldn’t function. Some days, getting out of the home was a major victory. The more I read, the more I felt the parallels between his life and mine.
One of the first questions Bakewell tackles is: Should you live openly?
Montaigne’s answer is yes. Even when it’s bad.
Too many people in this system try to hide. They want to present one version to the judge, another to the family, another to the lawyer. It all starts to sound like a strategy. But judges can tell. They don’t want a script. They want consistency over time and authenticity.
Should you pay attention to what you’re thinking?
Page 31 includes the line: “He began watching and questioning his own experience in writing down what he observed.” Montaigne didn’t wait until it was safe or the right time to reflect. He wrote while it was still unclear and fresh in his mind.
If you wait until your lawyer tells you it’s time to write, you’ve already missed the part where the story could have been honest. Most people say, “I’ll get to it when I’m ready.”
But by the time they feel ready, someone else (like the Department of Justice) has already defined their narrative.
Should you take responsibility for what you justified?
Yes. And Montaigne doesn’t let himself off easy. He writes about cheating at games and feeling proud of it. He doesn’t ask for forgiveness. He examines what made it feel right at the time.
That’s where most sentencing statements fall flat. People say, “I take responsibility,” but they don’t explain how they used to think. They say, “This was my first offense,” or “I’ve never had a speeding ticket,” or “I’ll never do it again.” None of that proves anything. It’s wasted, useless content. Worse, it hurts them.
The court doesn’t just want remorse. It wants an explanation, a plan on how this will never happen again. What logic did you use to cross the line? And what makes you certain you won’t use that logic again? You cannot do that unless you embrace your prior justifications and excuses.
Should you stop fearing what hasn’t happened yet?
Montaigne feared death for years. He read Stoics. He rehearsed his funeral in his head. Then he almost died. And in that moment, he said it wasn’t fear, it was calm. Just a few uncomfortable moments at the end of life.
That resonated with me when I read it on the plane home from New York. In retrospect, I realized how terrified I really was of prison. I thought it would be the worst thing that could happen. And then I got there. And I thought, “What was I so afraid of?”
Someone we work with was notified that he was a target. He was overwhelmed. He couldn’t sleep. Couldn’t eat. Couldn’t work. We got him a lawyer. He prepared for a proffer. It went well. And nothing came of it.
He had been consumed by something that hadn’t even happened. And it never did.
Has your perspective changed?
If it hasn’t, what are you doing?
Before I went to prison, I told people I’d learn Spanish. Maybe get in better shape. That was it. I figured it would be a wasted year. I’d probably never talk about it again.
And then I got there, found a mentor, and slowly started getting on track. I started writing. I read books I never thought I’d touch. I started studying philosophy. I started learning from Michael and documenting my journey—the bad, the embarrassing, and the ugly, but also the growth!
Go read my early blogs. Some of them are awful. But they’re honest. I didn’t clean them up. I left them as they were. Because that’s what I was thinking at the time. And even when I cringe at them now, I’m still proud of the fact that I was willing to write them.
Should you write to understand or to impress?
Montaigne carved “What do I know?” into his ceiling beams. He wasn’t writing for other people. He was writing to figure out how he thought. That’s what this is about. Not just writing what sounds good. Writing what’s true, even if it’s messy and embarrassing.
Some people are afraid to start because they think it has to be perfect. It doesn’t. It just has to be accurate. That’s what people will trust.
What are you avoiding?
Page 250 includes a quote I’ve sent to a number of people:
“People involve themselves because they want to have an air of consequence or to advance their private interests or simply to keep busy so that they don’t have to think about life.”
I sent the whole book to someone once. He didn’t read it. So I sent just that one page.
He read it. Then asked, “What’s the point?”
I said, “You play softball five days a week. You complain about what’s in the prison commissary. Meanwhile, your wife is calling me crying. You already know what matters. You’re just not dealing with it.”
That conversation helped change the way he served his short sentence for wire fraud.
He finally accepted reality and started writing.
Page 33 includes the line:
“To see the world exactly as you did half an hour ago is impossible.”
Montaigne let himself change. He let the contradiction stay in. One day he said one thing. The next day he said the opposite. Not because he was lying, but because his thinking evolved.
That was me, too. One day in prison, I’d write, “This is a waste of time.” Three days later: “This is the most productive experience of my life.”
Those things both came from me. They’re both true.
You’re allowed to change. What matters is whether you’re recording the change while it’s happening.
One of the most important lessons from this book isn’t about virtue. It’s about position. There’s a story on page 80 about King Henry II. He kept shifting policies. One day he banned Protestant books. The next he allowed worship. Then he reversed again. Bakewell writes: “He moved back and forth, satisfying no one.”
I’ve done that. I’ve tried to speak to everyone at once. Early on, I’d try to make sure my message landed well with judges, defense lawyers, probation, defendants. I was trying to keep everyone happy. And it didn’t work.
A professor once told me not to mention Ayn Rand again during a lecture. She didn’t like the idea of selfishness. I said no. I had to be honest about what influenced me. I wasn’t going to sanitize it to please a crowd.
If you try to satisfy everyone, you’ll satisfy no one. And if you try to prepare without writing, without documenting how your thinking is changing, you’ll have nothing to show for it.
So the question is:
What are you writing today that’s going to matter to a judge, a prosecutor, or your own family two years from now?
Justin Paperny
