βThe most dangerous decision you can make is deciding the ending before even attempting to improve it,β I told him.
I was in New York to speak at a Goldman Sachs investment conference. After the presentation, I stayed behind to answer questions and talk privately with people who wanted a few minutes one-on-one.
One of them was a fifty-nine-year-old physician.
He had reached out the week before. After our call, I invited him to attend the event as my guest and suggested we sit down afterward before I flew back to Los Angeles.
When we met, he didnβt ease into it.
βIβve been indicted,β he said. βKickbacks to marketers. It went on for years.β
He explained that one of the marketers had been charged first and, through wiretaps, the government built its case against him. He didnβt argue the facts or minimize what had happened. He spoke calmly, almost mechanically, as if he had already walked himself through the outcome.
βIβll lose my license,β he said.
βIβll lose my money.β
βAt my age, recalibrating isnβt realistic.β
He paused.
βIβve been a doctor my entire adult life. I donβt know how to do anything else.β
There was no anger in it. No self-pity. Just acceptance.
βIβm already thinking about leaving New York,β he continued. βBetween the cost of living and the shame that comes with this, I donβt see a reason to stay.β
I listened.
After a moment, he added something Iβve heard from defendants more times than Iβve heard my kids say, βDad, can I go on YouTube and watch Mr. Beast?β
βNo offense,β he said, βbut this was easier for you.β
I didnβt interrupt.
βYou were whatβthirty? No kids? Easier to start over. Iβm a doctor. Iβm not a natural communicator like you.β
He gestured toward the conference badge on the table.
βYou just spoke in front of thousands of people.β
Minutes earlier, senior executives from Goldman Sachs had come up to shake my hand. One managing director told me it was a shame I wasnβt allowed to work at the bank, that my experience and knowledge would be valuable there.
He wasnβt resentful. He said it as if the comparison closed the discussion.
Hearing it didnβt prompt the doctor to consider whether his own experience might still have value. It confirmed the opposite.
Iβm too old.
Iβm a doctor.
Iβm not built for this.
Rather than focus on his questions about what prison would be like, I asked him a question.
βDo you know Theseus?β
He shook his head.
βCan I tell you a story?β
βOf course.β
βIn ancient Greece,β I said, βAthens sent young men and women into a maze or labyrinth as tribute. Inside was the Minotaurβa creature so dangerous that once you entered, no one ever came back.β
He leaned back in his chair, listening.
βEveryone who went into the maze before Theseus accepted the same assumption youβre making right now,β I said. βThat once you enter, the ending is already decided.β
βThey just went in to die?β he asked.
βSome fought,β I said. βThey ran. They tried to endure it. They all died.β
βBefore he entered the labyrinth, he spoke to Ariadneβthe daughter of the king who built the maze. She had watched every man before him enter.β
βTheseus listened,β I said. βNot because he was fearless, but because heβd seen how it ended for everyone else.β
βSo what did he do differently?β the doctor asked.
βHe didnβt go in empty-handed,β I said. βAriadne gave him a thread.β
The doctor waited.
βThat thread wasnβt a weapon,β I said. βIt didnβt make him physically stronger. It didnβt guarantee anything. It just made sure that every step he took into the maze was connected to a way back out.β
βSo whatβs the thread?β he asked.
βFor me,β I said, βit started with deciding how I wanted to live in and out of prison.β
I told him that when my securities licenses and real estate license were gone and my reputation had been destroyed, I believed many of the same things he was saying now.
That Iβd never rebuild.
That Iβd never make real money again.
That Iβd never get married.
That whatever came next would be smaller and permanent.
βMeeting Michael Santos didnβt change what had already happened to me,β I said. βIt changed what I did next. He told me to think about the end before the beginningβto start building assets that didnβt yet exist.β
I told him that meant writing every day when no one was asking for it, documenting work that no one may read, and preparing for a future that felt uncertain.
βIβm not telling you building new assets will work exactly as you hope it will or keep you out of prison,β I said. Clint Eastwood once said, βIf you want a guarantee, buy a toaster.β In my case, I knew that if I didnβt invest the time to create a new narrative, this experience would define me forever. And as simple as it sounds, thatβs not the person my parents raised.β
βThis Minotaur story sounds fatalistic,β he said.
βIt sounds practical,β I said. βEveryone Athens sent before Theseus had watched the same thing happen. No one returned.β
βBut they fought, right?β
βYes,β I said.
βAnd it didnβt help?β
βIt didnβt,β I said. βBecause the Minotaur never chased them. The labyrinth wore them down first.β
He leaned forward. βWhat do you mean by that?β
βThe repetition. The confusion. The exhaustion,β I said. βBy the time they reached the center, they werenβt thinking clearly anymore.β
βSo they didnβt lose because they were weak.β
βNo,β I said. βThey lost because they entered trying to survive the same way everyone else had.β
He sat back. βAnd youβre saying thatβs what happens to defendants.β
βIβm saying thatβs what happens inside the system,β I said. βPeople donβt question the approach. They repeat it.β
βRepeat what?β
βThey explain,β I said. βThey argue facts. They behave as if the outcome is already fixed.β
βAnd thatβs the mistake.β he said.
βThatβs the maze. Theseus doesnβt accept the same premise. With guidance from Ariadne, he doesnβt accept that entering means disappearing.β I said.
βBut he knows the Minotaur is real.β
βHe knows,β I said. βThatβs why he plans how to leave before he enters.β
He nodded slowly. βI see what youβre doing. This is still mythology.β
βLet me give you a real example,β I said.
βClyde Gibson. Different facts than yours. Different charge. Same assumption.β
βWhat assumption?β
βThat the ending was already decided.β
I told him Clyde pleaded to one count of aiding and abetting false tax returns. I told him Clydeβs lawyer said to expect prisonβtwelve to eighteen monthsβnot as a possibility, but as the likely outcome.
βAnd Clyde believed that?β
βHe didnβt argue with it,β I said. βHe just didnβt let that be the end of the story.β
βWhat did he do differently?β
βHe started preparing before sentencing, before the plea agreement, before the probation interview,β I said. βHe wrote his narrative early. He documented his work. He volunteered. He led for his family, setting the tone that nothing would stop him from trying to earn the best outcome. He did a beautiful job of doing the work on days he would rather do just about anything else.β
βAnd these cynical stakeholders noticed?β
βThey did,β I said. βProbation noticed. The judge noticed. Even the prosecutor said something unexpected in open court.β
βThat Clyde wasnβt a threat and didnβt appear likely to reoffend.β
βAnd the sentence?β
βProbation.β
He exhaled. βSo preparation changed the outcome.β
βIt changed how the system responded to him,β I said. βThatβs different.β
He nodded. βSo the thread isnβt optimism.β
βNo,β I said. βThe thread is refusing to accept an outcome too early.β
He sat quietly.
βSo youβre saying the system doesnβt really change.β
βIβm saying the structure doesnβt,β I said. βThe prosecutor still controls the case. The judge still decides the sentence.β
βThen what actually changes?β
βHow you enter it,β I said.
βThe investigation, the PSR, sentencingβwhatever comes next. Again, most defendants enter assuming the outcome is fixed, so they behave as if it is.β
βSo they stop doing anything that could change it.β
βWhy change if you donβt think it will help?β I said. βMost people in crisis react instead of build.β
βAnd the prosecutor?β
βThe prosecutor doesnβt need to react,β I said. βThey already framed the language.β
He paused. βSo the Minotaur is the prosecutor.β
βThe Minotaur is the system,β I said. βThe prosecutor is part of it.β
βAnd it doesnβt chase.β
βNo,β I said. βIt waits.β
He nodded slowly. βSo people walk into it exhausted.β
βThey do,β I said.
βAnd Theseus avoided that.β
βTheseus avoided entering blind,β I said.
He looked down at his hands.
βSo when I leave here,β he said, βnothing about my case changes.β
βThatβs right. But you have a choice on how you enter the maze,β I said.
He sat quietly.
βI called you,β he said. βI came here. Iβm not pretending this will be easy.β
βI wouldnβt believe you if you said it would be,β I said.
He gave a small nod.
βIβll be back in Los Angeles and back to work tomorrow,β I said. βWe can continue then.β
As we stood up, he said, βSo the thread is the work.β
βThe thread is refusing to wander,β I said.
Discussion Questions
1: What have you stopped doing in your case since someone told you to βexpect prisonβ β writing, documenting, asking for feedback, preparing β and who told you that?
2: Which part of your case are you currently treating as finished even though sentencing hasnβt happened yet β and what evidence supports that belief?
3: If a probation officer or judge reviewed your actions from the last 30 days, what would they see that shows you didnβt decide the ending early?