Preparing Before Sentencing: Don’t Let the Judge Guess Who You Are

When I was indicted for securities fraud, I wasn’t thinking about sentencing guidelines or mitigation strategies. I was thinking about how I had destroyed my career, humiliated my family, and ruined my reputation. I was in panic mode—like most people are when they find out the federal government is coming after them.

But here’s what I’ve learned since—and what I now spend my life teaching: you have more control than you think. Not over the charges. Not over the prosecutor. But over how you respond, how you prepare, and how you influence what happens next.

If you’re reading this, there’s a good chance you—or someone close to you—is under federal investigation or heading toward sentencing. You might feel like your life is over. I get it. But it’s not.

Let’s talk about what actually matters right now.


Understand What the Guidelines Are—And What They Aren’t

When I first met with my attorney, he started talking about “the sentencing guidelines.” I nodded like I understood, but I didn’t. I didn’t know that these guidelines were the framework judges use to calculate a sentence based on your offense level, your criminal history, and other factors—both aggravating and mitigating.

What I also didn’t understand was this: those guidelines aren’t fixed. Judges have discretion. And what you do between your plea and sentencing hearing can absolutely influence what they decide.

If you don’t know where you stand on the guidelines—or how to influence them—ask. Learn. Get help. Preparation is not optional. It’s everything.


Mitigation Isn’t a Buzzword. It’s Work.

Mitigation means creating a full picture of who you are—beyond the crime. That takes effort. You need to build a documented body of work that proves you’re more than your worst decision.

I first started to grasp this when I was in prison, talking to my friend and now-business partner Michael Santos. He had been down a long time by then, and he asked me something that stuck:

“If a judge only knows you through your plea agreement and a PSR, do you think they know you at all?”

The answer, of course, is no.

That’s why mitigation involves:

  • Writing your personal narrative—honestly, with remorse, without spin.
  • Gathering character reference letters—from people who know your values.
  • Pursuing therapy, community service, or restitution if it applies.
  • Reflecting on your mistakes and documenting how you’re changing.

No one’s expecting perfection. But they do expect effort. And if you’re not showing it, they’ll assume you don’t care.


The Right Mentor Can Change Everything

Before prison, I thought I had to figure this all out myself. I didn’t. Michael helped me understand three things that reshaped how I approached confinement—and eventually helped me rebuild my life:

1. Document Growth

Every day, I journaled what I learned, what I regretted, and what I was working on. That record became the foundation for my personal narrative.

2. Create a Plan

I didn’t just “do my time.” I created a schedule. I set goals. I developed habits that helped me stay focused on what came next.

3. Communicate With Purpose

Whether I was speaking with my judge, my lawyer, or my family, I was honest. I didn’t downplay what I did. I focused on who I was becoming.


Own It—Or the Judge Will Assume You Haven’t Changed

I’ll be blunt: if you can’t take full ownership of your actions, you are not ready for sentencing.

One question I ask every client is this:

“What do you want the judge, your victims, or your kids to say about you five years from now?”

That question changes how people think.

Because the reality is, no matter how much your attorney prepares, you will be the most powerful advocate for your future—if you take the process seriously.


Post-Sentencing: It Doesn’t Get Easier—But It Can Get Clearer

After I came home from prison, nothing magically got better. I had to rebuild my network, start over professionally, and deal with the consequences I’d created.

But because I’d put in the work before sentencing—and during confinement—I didn’t walk out feeling lost. I had a foundation. I had a plan.

If you don’t build that now, you’ll carry the same confusion and fear into your post-prison life. And that’s when people make more bad decisions.


If You’re Frozen by Fear, Start Small

You don’t need to fix everything today. But you do need to move.

Here’s what I’d do if I were starting over again right now:

  • Learn how the sentencing guidelines apply to your case.
  • Write your story. Not for sympathy—for clarity.
  • Build a team—mentors, not just lawyers.
  • Start living like the person you want the judge to see.

Because when you walk into that courtroom, you get one shot to show who you are. Don’t waste it.


You Don’t Need Hope—You Need a Plan

You don’t need to “stay positive.” You need to prepare like your future depends on it—because it does.

And you don’t have to do it alone.

Every Monday at 1 p.m. Pacific, we host a live webinar. You’ll hear real stories, ask real questions, and learn the exact strategies people use to earn better outcomes in court and in prison. Show up ready to work—it could change everything.

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