Why “I Made a Mistake” Fails at Federal Sentencing

I finished listening to Free Will by Sam Harris last evening, and I wanted to immediately memorialize some thoughts. Our message is that we are not going to ask you to do what we have not done and documented. So I picked up the book selfishly, to learn. I learned a lot from it, and I realized how many mistakes I made before sentencing and even after I came home from federal prison when I tried to describe what I had done.

For nearly 20 years, I have worked with people going through all stages of a government investigation, sentencing, prison, and rebuilding. I have also spent years asking myself how I went from USC, to working as a broker, to sitting across from FBI agent Paul Bertrand and lying, becoming a convicted felon, and eventually going to federal prison.

For a long time, my answer was simple: I made bad decisions without considering how they would influence the rest of my life. That answer is true, but it is incomplete.

Sam Harris makes an argument that I know some people will reject. He writes that we do not necessarily choose our thoughts before they appear. We do not choose our genetics, parents, childhood, fears, intelligence, early experiences, or many of the events that shape us. Even when we feel like we are making a conscious decision, he argues that the decision comes from conditions we did not create.

It can be a tough book to take in. The audiobook is only about an hour and 14 minutes, but I kept going back 30 seconds because I wanted to hear something again. At the same time, I could see the danger in bringing this argument into my business. Someone dealing with a government investigation could hear, “My decisions came from conditions I did not create,” and turn that into, “It was not really my fault.”

Imagine leaving that impression with a sentencing judge. Imagine how it could sound to a victim. You may never directly say it was not your fault, yet it can come through in the narrative you write and in the way you explain your conduct. The court is going to hold you responsible. The people you hurt may hold you responsible. Your family may hold you responsible. Free will cannot become an intellectual excuse for what you did.

I Did Not Become Dishonest When the FBI Arrived

When the FBI came to see me, I made the investigation worse. I lied, blamed, and excused. Harris wrote another short book called Lying, where he discusses the reasons people lie. One reason is obvious. We want to protect ourselves. We do not want to be seen negatively, and we want to get through the situation without confronting what the truth could cost us.

I lied to the FBI in part to protect my reputation, career, and freedom. I did not suddenly wake up and become dishonest when the agents arrived. Looking back, I can see that I had made many bad decisions over a sustained period of time. Those decisions brought me to that meeting and made it easier for me to lie once I got there.

The sequence matters. I have said many times on stage, on television, and in conversations with defendants that a person does not wake up one morning and randomly decide to destroy his life. Especially in white-collar crime, it may begin with a financial problem. Someone has to hit the quarter, make more money, protect a bonus, or keep up a lifestyle. He begins to conceal the problem and that concealment works for a while. Money keeps coming in, clients remain happy, the bonus gets paid, and the family continues living as they had before.

The fact that it worked matters. The next lie becomes a little easier, and then another lie sits on top of that. After enough time, someone becomes capable of conduct that he might have considered impossible earlier in his career. He could have once said that stealing, embezzling, lying, or taking shortcuts was not in his character, and he may have believed it. But the change happened slowly over years. By the time an FBI agent knocked on my door, lying was much easier than it would have been when I was a student or at the beginning of my career.

That is the story too many people skip when they prepare for sentencing. They focus on the day the government arrived, the indictment, or the plea. They say they felt pressure and did not have bad intentions. Then they jump to, “I am sorry, I learned my lesson, and it will never happen again.”

The years before the investigation tell us much more. Somewhere along the way, the person first ignored something he knew could be wrong. Later, he concealed it. Protecting income or status became more important than telling the truth. At some point, he convinced himself there was no other option, or that the lie had worked and he would not get caught. Eventually so many lies were protecting the original lie that it no longer felt abnormal.

Calling all of that a mistake does not explain it. How many mistakes were there? Ten? Fifty? A thousand? Saying, “I am a good person who did a bad thing,” does not explain it either. A sentencing judge is left to wonder why the conduct continued and why this person is unlikely to return to another courtroom. A future employer, business partner, or funder may have the same concern when that person comes home.

Michael Santos challenged me on this while we were in prison together. I told him I had made a mistake, and he asked whether it was a mistake or a bad choice. He wanted me to think about the mannerisms, thought process, and rationalizations behind my decisions. When did I know it was wrong? How did I convince myself it was acceptable? Was it because other people were doing it? Was I influenced by the corporate culture or chasing a bonus?

Okay, that is a start. But stop calling it a mistake.

What Actually Changed?

A more honest explanation would sound something like this: I am responsible for what I did, and I am investing the time to understand the conditions, habits, fears, and decisions that allowed me to continue doing it. I know that saying I will never do it again means very little if I cannot explain the sequence that brought me there.

That is where I see the connection between Free Will and mitigation. Harris does not argue that people cannot change. He argues that change requires causes. A person cannot announce that he has changed and expect everyone else to accept it. He has to create conditions that make different behavior more likely.

Losing a professional license or being removed from an industry changes some conditions. Someone who can no longer work as a lawyer or stockbroker may have lost access to the environment connected to the crime. That does not explain how he will respond to pressure in a different business. The more important question is what he has done with the time since the conduct became public.

For one person, that could include therapy or treatment. Someone else may begin paying restitution and thinking seriously about the people harmed. New professional boundaries may matter. So might honest conversations with family, community service that is actually documented, a release plan, or public writing about what happened. The specific acts should connect to the conduct instead of becoming a list of activities collected shortly before sentencing.

You can borrow someone else’s words. You can copy an apology or write that you plan to become a law-abiding, contributing citizen. That may read well in a sentencing memorandum, but where is the evidence? I recently filmed a video about someone who mimicked language Michael Santos has used for years and put it into his own narrative. The judge saw words on paper without any evidence that the person had actually been living them.

That is why I tell people to build a record. The record should show what you have done between the old conduct and the next difficult decision. It gives a probation officer, judge, case manager, future employer, or family member something more than another promise.

What I Had to Understand About Myself

This part of the book forced me to think again about what drove me. When I was 25 or 26, I was making about $500,000 a year and had seven figures in the bank. How much money did a 25-year-old need?

For me, the title mattered greatly. Being described as a young broker at Bear Stearns made me feel important. I liked how I was perceived, and I was very influenced by my environment. Losing that title was more staggering to me than losing the income. I think it affected my parents too, truth be told.

That tells people more than, “I made a bad decision.” It identifies something I needed to understand about myself. A person whose identity was tied to title and income should be able to explain what he is doing after losing both. Someone whose pride kept him from asking for help should be able to identify who he speaks with now. A family that had no idea what was happening may need honest information today. A person returning to the same industry where he crossed the line should be able to describe the boundaries that now exist.

None of those answers guarantees a result at sentencing. They give other people a way to evaluate whether the claim of change is supported by anything.

Shame Can Become Another Excuse

Too many people live in shame and repeat, “I am sorry. I will never do it again.” Shame can become their identity. It keeps them in bed while they tell themselves they are bad people, they ruined everything, and they will never forgive themselves.

I understand those feelings. But suffering can become another way to avoid the decisions that caused the problem. Someone may think, “I feel terrible, so that proves I am accountable.” He can suffer for months and still learn very little about how he got there.

At some point, he has to begin undoing the sequence. That may mean writing honestly about what happened, telling a truth he has avoided, looking for a job that feels beneath the career he lost, or finally acknowledging the people he blamed for too long. Those daily decisions begin to create different conditions for his life.

This book also reinforced my problem with people in the prison consulting industry who sell certainty. Outcomes are shaped by thousands of conditions, so nobody can honestly guarantee a lower sentence, admission into RDAP, designation to a specific federal prison, home confinement, or how a judge will respond. You can influence some of the conditions without controlling the result. You can tell the truth to the probation officer and the government, build a record before sentencing, create a narrative and release plan, and document how you are addressing the sequence that brought you into the investigation.

Anyone promising a specific result is ignoring all the people and variables standing between what you do and the result you want.

What I Took From Free Will

Listening to this book also pushed me to think about compassion. People in our community have hurt others and created victims. Those victims may have lost money, careers, trust, and years of their lives. Studying what compelled someone to cross the line does not erase that harm. It can help us understand the full person and reduce the chance that the conduct happens again.

The same thinking applies to prosecutors, judges, probation officers, prison staff, family members, and victims. Their decisions and reactions come from their own experiences, incentives, fears, duties, and the information in front of them. Calling the prosecutor evil, insisting the judge does not understand you, or complaining that your family should support you differently does not help you examine your own conduct.

I do not know whether Sam Harris persuaded me that free will does not exist. I am still thinking about it. I do know that most people going through a government investigation do not need to give a judge a lecture about determinism. They need to trace their own sequence honestly.

The question I took from the book is simple: What conditions made my conduct possible, and what am I doing now to make that conduct less likely?

That question belongs in a sentencing narrative, probation interview preparation, a release plan, prison adjustment, and the years after someone comes home. Study the sequence instead of repeating that you learned your lesson. Explain what the lesson was and show people how you are living differently.

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