Someone in our community said to me, “Dude, that Plato allegory story really stuck with me. Got any more?”

That question changed how I approached this newsletter. I wanted to write more about the ideas that influenced my prison term and less about how to prepare for a government investigation. Of course, it’s all connected. But not everything needs to sound like, “Did you hear what Judge Bennett told Michael Santos about how to question the offense conduct in the probation report?”

Our Tuesday webinars cover sentencing and prison issues. (By the way, on Tuesday, we’re doing a live encore of the BOP webinar on the new directivethat sends eligible people straight to home confinement instead of the halfway house.)

These newsletters are where I reflect on the philosophy, ethics, and literature I spent time with in prison and continue to revisit today. I write about them partly for myself, and also with the hope that they’re useful to others going through difficult or uncertain moments. Right now, I’m working through The Stranger by Camus. If I can make sense of it, I’ll share insights for our community. Right now, it feels like a book about a man being punished for being honest, or at least for being himself.

Next to my water bottle and iPhone are three books I’m reading and listening to (retention improves when you read and listen to the same book). The three books are A Life of Montaigne, How to Grow Old, and Aristotle’s Way.

Someone recently asked me, “What was it like serving time with Michael?”

When I surrendered, he had already served 22 years. To put it lightly, his routine was deliberate. Everything was intentional. I don’t have the space in this newsletter to describe it fully, and even if I tried, I wouldn’t do it justice. If you want a clearer picture, read Earning Freedom. It documents exactly how he lived, day after day.

What I admired most was that he was an individual who pursued his own ideas, thoughts and was never persuaded by people who did not share his value system. Criticism then and now means nothing to him. I admired that because I was a guy in my 20s who was afraid to stand out, to take a position. I went with the flow, and in so doing, was easily forgettable.

People often say, “You were lucky to meet him.”

Maybe. But a lot of people went to prison during the 26 years he served. He met a lot of “Justins, ” people with good degrees from good families who never imagined they would go to prison. They could have learned from him. Many did, and many didn’t.

I was willing to learn and take feedback that wasn’t always easy to hear. I was also willing to try and invest the time to own my story.

After my release, Michael and I communicated through letters and eventually email. We were not allowed to visit. I would update him on my plans, what I was learning, and the feedback I was getting from speaking and consulting.

I enjoyed updating him on literature I was reading or rereading, including The Prince by Machiavelli.

Justin Paperny and Sandra standing outside the Church of Santa Croce in Florence After Visiting Machiavelli’s Burial Site, and In Front of The Statue of Machiavelli

The Prince is not a book about how to be liked, that much is for sure. It’s a book about how power actually works. One line stuck with me:

“A prudent man will always try to follow in the footsteps of great men and imitate those who have been truly outstanding, so that, if he is not quite as skillful as they, at least some of their ability may rub off on him.”

That line explained how I viewed parts of my relationship with Michael. I wasn’t trying to copy him. I wasn’t looking to become the next him. I was genuinely trying to learn from him, so I could become better.

Machiavelli doesn’t praise people for their intentions. He points to results.

The obsession with results is partly why I didn’t enjoy my release from prison. I always asked myself: What did I do today? What can I point to that shows I followed through? Am I still on track?

Despite being an avid golfer, I did not pick up a club for six years after my release. I had not yet earned the right to “play or have fun.” I had too much to do and could not afford distractions.

After my release, I re-read Atlas Shrugged by Ayn Rand. It’s a big book. It makes people uncomfortable, and a simple Google search will reveal how some individuals feel about Ayn Rand.

The book centers on what happens when people who build, create, and take risks are told they’re selfish or destructive, while the people who avoid responsibility are rewarded. The main character, John Galt, walks away from a system that punishes independence and effort. His opposite, James Taggart, avoids taking a stand, avoids risk, and never builds anything of his own.

I wrote a letter to Michael after reading the book: “I do not want to be James Taggart.”

That goal still matters to me. Like Galt, I want to live independently, to create, and to contribute regardless of whether people understand or approve.

Not long after that letter to Michael, I stayed up all night editing one of my first videos. My newborn daughter Alyssa was next to me, asleep. I was proud of what I made. Then I checked the first comment:

“What a loser you are, talking about writing a blog in prison that no one reads. At least you got one comment now on this video with 25 views. Go back to your cave, you cheater and thief. No one asked, nor cares what you think. And your mic sucks too. Did you not steal enough as a broker to buy a decent mic?”

When I read that comment, I wasn’t upset. I found something positive in it: “Wow, 25 views. That’s better than 24. And I said something that compelled someone to respond. I’m trying. I’m out there. Let’s keep doing this. And he’s right, I do need a better mic.”

I responded to his comment, thanking him for the feedback, especially the part about the mic.

I never would’ve done that before prison. James Taggart would never have put himself out there to try.

One line from the book stayed with me:

“You can avoid reality, but you cannot avoid the consequences of avoiding reality.”

That was me before prison. I avoided hard talks and did the work. I was lazy, useless.

Most people I meet who are going through this system aren’t useless or lazy like me, but they are still avoiding something. They delay writing their narrative. They wait to build a release plan. They put off introspection or examination of how they ended up here. Delays always cost more than they expect.

Another line from Rand:

“A creative man is motivated by the desire to achieve, not by the desire to beat others.”

After prison, that became my approach. I wasn’t trying to outdo anyone. I wasn’t building a platform to win approval. I was trying to create something that reflected who I was becoming. I wanted my record, my work, to speak for itself. To my parents, my future wife, and my unborn children.

I have shared this line with hundreds of people:

“The hardest thing to explain is the glaringly evident fact which everybody has decided not to see.”

That describes so many people involved in a government investigation. Everyone knows what’s wrong. But nobody says it plainly. So it stays broken.

Another quote:

“The ladder of success is best climbed by stepping on the rungs of opportunity.”

For me, that meant learning from Michael, then taking small, uncomfortable steps. After prison I walked into law firms that didn’t expect me. I gave free talks. I wrote blogs when I wasn’t sure anyone was reading. It wasn’t close to perfect. But it kept me moving. And each step made the next one a little easier.

And finally:

“Throughout the centuries, there were men who took first steps down new roads armed with nothing but their own vision.”

That’s what Michael did. He didn’t wait for an audience. He didn’t wait for approval. He started documenting his progress when nobody asked him to, with 26 years left to serve. That gave people like me something to look at—not to copy, but to learn from.

Machiavelli wrote in The Prince:

“The wise man does at once what the fool does finally.”

That’s the test.

Will you act now, or wait?

What are you avoiding that already needs your attention?

Are you learning from people who’ve done the work, or just listening to what makes you feel comfortable?

What are you building today that belongs to you, not borrowed, not delayed?

As I wrote in last week’s Montaigne newsletter, he said:

“I change only because I do not see the world today as I did yesterday.”

That quote captured what happened when I revisited The Prince and Atlas Shrugged after my release. Those books meant one thing to me in prison and something entirely different when I came home and actually tried to implement the lessons I had discussed with Michael. In prison, it was easy to underline a quote or talk about self-discipline. But once I came home and had to live it, when no one was watching, when no one cared, the ideas took on a different meaning.

Most people delay. A few start.

Which one are you?

Next week, I’ll share the story behind the Rockefeller quotes someone in our community sent me and why quoting ambition without effort never works.

Justin Paperny