White Collar Advice | Thursday Newsletter | April 17, 2025
For a long time, I told myself I had it handled.
That was the lie I used to get through each day. I didn’t say it out loud—but I believed it. I thought the judge would figure it out. That my past success and clean record would carry me. That I could keep quiet, go along with the process, and still come out okay.
I was wrong.
And the longer I pretended, the worse it got.
It wasn’t until I admitted how little I actually knew—about the system, about what mattered, about myself—that things began to shift.
I asked for help. I got it. And that’s when I started what has now become a lifelong process of learning.
At Taft, I read everything I could get my hands on—most of which I didn’t fully understand. I’d bring it to Michael. We’d walk the dusty prison track and talk it through. One day, he handed me a passage from Plato’s Republic—the Allegory of the Cave—and we spent an hour breaking it down. At first, it sounded like abstract philosophy. But it turned out to be the most accurate description of the exact mistake I’d been making for years.
In Plato’s story, a group of people live chained in a dark cave. Their heads are fixed—they can only look forward. Behind them, a fire burns. Between the fire and their backs, people pass by holding up objects. But all the prisoners see are the shadows cast on the wall in front of them.
And those shadows become their truth.
Then one of them breaks free. At first, the light blinds him. It’s painful. But eventually, he sees the fire. He sees what’s behind him. And then he climbs out of the cave and sees the real world—sunlight, trees, truth, clarity.
He goes back to tell the others.
They laugh at him. They don’t believe him. They think he’s the one who’s lost.
They’re too invested in the illusion. They’d rather keep staring at the wall.
When I read that, I realized how long I had been facing the wrong direction. How long I had been hoping the image on the wall would change—without ever turning around to understand what was really behind it.
I wanted to believe I was different. That prison was a misunderstanding. That my resume and good intentions would be enough.
They weren’t.
A few days ago, I found an old photo of me as a kid—standing next to Fernando Valenzuela. My parents took it with a Kodak camera, like everyone’s parents did back then.
Kodak defined photography. They were everywhere. Unshakable.
And they invented the digital camera in 1975.
A Kodak engineer built the first working prototype and showed it to leadership. They buried it. They were afraid it would destroy their film business.
They saw what was coming—and looked away.
They turned back to the wall.
By the time they embraced digital, it was too late. In 2012, they filed for bankruptcy.
Around the same time Kodak buried its own invention, Blockbuster had a chance to buy Netflix—for $50 million.
They didn’t just say no. They laughed them out of the room.
Blockbuster executives were convinced their business model—thousands of retail stores, late fees, shelf space—was too strong to be threatened. They stuck to what had always worked. They didn’t adapt. They didn’t want to see what was coming.
Netflix turned around. They saw what was real. They left the cave.
Blockbuster didn’t. And now there’s one store left in Oregon.
That’s what happens when people stay in the cave—even when the exit is right in front of them.
And I still see it every day.
Last week, someone in Florida joined our community. On our first call, he told me that he hated confrontation. That he didn’t want to upset his lawyer. So for months, he stayed quiet—hoping things would work out.
But things weren’t working out.
His lawyer wasn’t returning calls. Hadn’t responded to the Presentence Report. Only reached out when it was time to get paid. And every time he asked a question, he got a dismissive answer: “Don’t worry. Judges don’t look too closely at that.”
He wanted to believe it. Because believing it was easier than pushing back.
But then something changed.
He started watching our videos. Reading. Listening to others who’d been through it. He realized he wasn’t preparing—he was avoiding. So he picked up the phone and told his lawyer, “I need a real plan. I need accountability. And if I don’t get it, I’ll find someone who will help me lead.”
He started writing his narrative. He’s building a release plan. For the first time, he’s not pretending.
He’s doing the work.
I reminded him of something Michael taught me during our walks: a line from the book Good to Great—
“What got you here won’t get you there.”
That line applied to Kodak. It applied to Blockbuster. It applied to me. And it probably applies to you.
So let me ask you directly:
Since joining this community, what have you done to show why you deserve leniency?
Since last week, what have you written or built that would help your judge or probation officer understand who you really are?
Since last week, what have you done that makes ignoring your effort impossible?
If your answer is “not much,” I understand. But be honest: are you still facing the wall?
Georg Hegel once wrote:
“What experience and history teach is this—that peoples and governments never have learned anything from history, or acted on principles deduced from it.”
That wasn’t just about institutions. That was about individuals. About us.
Below is something I wrote while with Michael while I was in prison. I had finally started to understand what I had done—and what I could do differently moving forward. It was the first time I started putting into words what it meant to leave the cave.
Chapter 19, Lessons From Prison, Page 164
Besides offering preventable lessons, I could also offer advisory lessons. Despite good intentions, bad decisions or life circumstances sometimes led us into adversity. This was a universal, human condition. When such challenges came, I hoped that those with whom I shared these lessons could find confidence to power through. We may succumb to temptations, but time immemorial offered countless examples of our resilience. We could thrive through turmoil and emerge stronger from adversity.
The question was would people listen. Plato, the immortal philosopher, wrote about the challenge of conveying lessons to be drawn from human experience. In his classic book The Republic, Plato told his story known as “The Allegory of The Cave.”
In that fable, Plato asked his audience to imagine a subterranean cave. A group of people had lived their entire lives in that cave. Not only were they confined to the cave, but Plato described their movements and perspectives being restricted because they had lived their entire existence fastened to a pole behind them.
As a consequence of their circumstance, the people in Plato’s cave could not comprehend or fathom the fullness of life. They had nothing more than what they could learn from their limited perspectives. By only being able to look straight ahead, they misperceived shadows for reality. Reflections from bouncing light rays brought illusions that those in Plato’s cave felt certain were authentic.
That life of limited perspective was all that the dwellers of Plato’s cave knew until one of the inhabitants broke free. He climbed out from the cave and emerged into all the splendor of the world. For the first time, he saw more than the reflection of light. He felt the power of light itself, with the sun beaming upon him and illuminating all around him. Suddenly life was more than a collection of shadows that he saw projected on the wall. Instead, he saw and experienced life itself.
Upon his discovery, Plato’s cave dweller returned to the subterranean chamber that had heretofore been his only world. He was eager to share the lessons that he had learned about the world, to help others exchange their illusions for the beauty of reality. Instead of embracing those lessons, however, Plato told us that the fellow cave dwellers rejected such descriptions.
People have a natural propensity, Plato’s allegory instructs, to perceive the world in accordance with their own perspectives. Conveying lessons from human experience represented one of man’s greatest challenges. That was why Hegel advised that we had a duty to record our histories. We had to do our best to instruct others in order to prevent the cycle of mistakes. What got you here won’t get you there. I would do my part to enlighten others through the lessons I learned.”
If you’re overwhelmed, I get it.
But don’t let comfort keep you facing the wall.
Write one paragraph. Ask one question. Make one call.
Because the longer you stare at the shadows, the more real they start to feel. And at some point, you forget there’s even a way out.
You don’t have to stay in the cave.
You can turn around.
You still have time.
—Justin
