In the invitation for this week’s webinar, I joked that maybe we could get through one session without talking about prison, the Bureau of Prisons, or the First Step Act. It wasn’t just a joke. It was a reminder to myself that the people who get the most value from our work aren’t only interested in policies or credits—they want to understand how to live better, think more clearly, and make fewer mistakes going forward.

That’s what I want to focus on this week.

What I’m about to share didn’t help me get out of prison early. It didn’t lead to a sentence reduction, and it didn’t earn me any favors. But it did help me get to a place where I could think critically about what I had done and what I wanted to do differently. That shift mattered more than I realized at the time, and it continues to matter now.

Michael introduced me to these ideas when I had no distractions left. He didn’t give me quotes. He gave me assignments. I had to read, underline, write, and then explain what I understood. If I couldn’t explain it clearly, I had to start over. That process became a form of structure, and eventually, a form of direction.

That’s why I still share these lessons. Not because they worked for everyone, but because they worked for me.

A Conversation That Came Too Late

A few days ago, while I was hitting golf balls with my son, I received a text from someone I hadn’t spoken to in months. He just wrote, “You were right.”

Later that night, we spoke for the first time in a while. He reminded me of a conversation we’d had earlier this year. At the time, he had just learned that he might be pulled into something serious. I encouraged him to begin preparing—not because a case was guaranteed, but because sitting still rarely helps. I told him he should start documenting what mattered to him, writing out his thoughts, and building something he could show to others later. Something honest. Something thoughtful. Something that would prove he wasn’t waiting for permission to improve.

He agreed, but then chose not to do anything. His lawyer told him it was too soon. The advice was to wait. So he waited.

Now he’s finding out that others involved in the same matter already took action. They have records. They’ve submitted materials. They’ve created a foundation. He hasn’t. There’s nothing to point to. There’s nothing to offer. And he knows it.

He wasn’t the worst actor in the case. But he’s now in the weakest position because he didn’t move when he had the chance.

Robert Greene – Strategy 18: Expose the Center of Gravity

One of the first assignments Michael gave me was to read The 33 Strategies of War by Robert Greene. He asked me to read it slowly, not to skim. Then he asked me to write about what stood out. The strategy that stopped me cold was Strategy 18—Expose the Center of Gravity.

That strategy is about identifying the one thing you’ve refused to confront. Until you name it, it will continue to influence everything you do. I had made dozens of poor decisions, but the pattern behind those decisions had gone unexamined. I had spent years focusing on the circumstances around me instead of the one constant—my own rationalizations.

When I finally took the time to name the core mistake, it wasn’t comfortable. But it gave me a clearer picture of why I had gone off track. Without that, I wouldn’t have been able to explain what happened—not to myself, and not to anyone else.

What have you refused to examine—not because it’s unclear, but because it forces you to take responsibility?

Strategy 7: Blitzkrieg – Move While Others Wait

The Blitzkrieg strategy is built around the idea that timing can be more important than precision. Greene explains that many people fall behind not because they make the wrong move, but because they make no move at all. The ones who act while others are still debating usually gain the advantage, even if their early steps are flawed.

That was the lesson the man in the text message had to learn the hard way. He waited for certainty. The people around him didn’t. They created records, they made decisions, and they were able to show initiative. He waited for clarity that never came.

That’s not uncommon. In the years I’ve been doing this work, the difference between people who struggle and people who gain some control over the outcome often comes down to movement. The people who start—even imperfectly—are the ones who eventually earn credibility. The ones who sit still run out of time.

What have you put off because you think starting now might not be perfect?

Strategy 12: Grand Strategy – Know When Not to Engage

Acting early doesn’t mean reacting to everything. There’s a difference between being strategic and being busy. Greene’s Strategy 12—Grand Strategy—explains the importance of conserving energy for the fights that matter. This was difficult for me to learn.

When I first started rebuilding, I wanted to explain everything to everyone. I answered every critic. I justified every decision. I thought if I could just say enough, I’d win people over.

That didn’t work. It drained energy and distracted me from what I actually needed to build. Eventually, I stopped responding to noise and focused on a small set of actions I could control. That’s when things began to improve.

Where are you spending energy that isn’t helping you move forward?

Strategy 4: Segment the Problem – Divide and Conquer

One of Greene’s earliest strategies is about breaking problems down so they don’t overwhelm you. When I started writing about my past, I didn’t write everything at once. I took one moment. One decision. Then I moved to another.

The idea was to build something over time that felt complete—not because it covered everything, but because each part was honest. That approach helped me stay consistent. It also made it easier to show people what I was doing to change.

Trying to do everything at once usually leads to paralysis. Working in small pieces is slower, but it’s what builds credibility.

What part of the problem can you take on now without getting stuck in the bigger picture?

Ayn Rand – Contradictions Don’t Exist

In Atlas Shrugged, Ayn Rand writes:

“Contradictions do not exist. If you think you’ve found one, check your premises.”

That quote stayed with me. I used to say I believed in transparency, but I hid from difficult conversations. I told myself I valued ethics, but I looked the other way when the decisions became uncomfortable. I claimed I wanted peace of mind, but I made choices that kept me anxious and on edge.

Rand’s writing wasn’t emotional, and it wasn’t subtle. It forced me to look directly at the lies I had told myself. Not the big ones—just the quiet ones that chipped away at how I lived.

Where in your life are you holding two opposing ideas—and pretending they both can be true?

Montaigne – Writing as a Way of Thinking

When Michael introduced me to Montaigne, I wasn’t immediately drawn in. The essays felt dense. But over time, one thing became clear—Montaigne wasn’t writing to perform or persuade. He was writing to understand himself.

One line that stuck with me was:

“I study myself more than any other subject. That is my metaphysics.”

That became my approach as well. Writing wasn’t about making an argument. It was about documenting what I had done and asking whether the story I was telling myself actually made sense.

Some people think the act of writing is about output. But for me, it became a tool for clarity. It gave me a reason to stop lying to myself. And it gave me something to revisit later when I wasn’t sure whether I was drifting again.

What would your own writing reveal about the way you’ve made decisions?

John Locke – You’re Already Writing

Locke’s theory of the Tabula Rasa is often misunderstood. People hear “blank slate” and assume they can start fresh at any time. But that’s not what Locke meant. He meant your slate is filled by experience, and it’s being written whether you realize it or not.

By the time I started writing, my record was already filled with decisions I had tried to ignore. Sitting still didn’t preserve anything—it just added more silence to the record.

Once I understood that, I began writing with purpose. It didn’t change the past, but it helped me shape what came next.

What’s already on your slate—and who are you allowing to write the next part?

Plato – The Cave Is Familiar, But It’s Not the Truth

Plato’s Allegory of the Cave describes people who have spent their entire lives staring at shadows on a wall. They believe the shadows are real because it’s all they’ve ever known. Then one person turns around and sees the fire—and realizes the truth.

When he goes back to tell the others, they mock him. They don’t want to turn around. They’re more comfortable staring at the illusion.

I thought about that often after I read it. Once you see clearly, you can’t pretend you didn’t. But you also realize how hard it is to get others to look. Over time, I stopped trying to convince everyone else. I just kept working, even when it felt quiet.

What do you know to be true—but still ignore because it’s easier not to act on it?

Why I Still Share This

Michael didn’t give me these books because he thought they’d entertain me. He gave them to me because they forced him to think more clearly. That’s what they did for me, too.

I still read them. I still underline. I still write. Not because I’m trying to hold on to something—but because the process keeps me honest. It gives me space to check whether I’m slipping into old patterns, or falling back into habits I worked hard to leave behind.

These newsletters are about staying connected to the values I say I believe in. And these thinkers help me do that. That’s why I still teach them.

Next Week – Envy

Next week, I’ll share what I’ve learned about envy.

Final Question

What have you avoided naming because it would require you to change something you’ve gotten used to?

Justin Paperny