Nine weeks ago, I gave a free course to an executive facing federal sentencing. He said family and freedom were his top values. I believed him—until he ignored the course and skipped key steps I recommended. Today, his probation officer is recommending 5 years, calling him elusive and evasive. Why? His actions didn't match his words. This happens constantly: defendants say they'll prepare, but they don't follow through. The government doesn't wait. If you say you value your freedom, show it. Start now.

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On May 19, 2009, I walked the track at Taft federal prison for the last time. Sixteen years later, I still remember the quiet commitment I made: to try. Not just talk. Try. I had written a blog, outlined a business, promised to cold call lawyers, pay restitution, and speak openly about my experience. I knew rejection would come—and it did—but I kept at it. That's the real test after prison: not what you say, but what you do. If you're serious, start now.

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Inaction is a decision. I once spoke with a corporate controller who suspected invoicing issues but clung to a civil attorney's opinion that it was just a dispute—not a crime. Seventeen months later, his co-workers (some more culpable than him) are now government cooperators. They acted. He waited. Now, they're likely to receive sentencing benefits for cooperating, while he's exposed. As Hunter S. Thompson said, "A man who procrastinates in his choosing will inevitably have his choice made for him by circumstance." If you're in trouble, don't stall—act now.

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Let Go of Entitlement: Why Starting Over Matters After a Federal Conviction

Most defendants resist the idea of starting over—I did too. I clung to my past: USC grad, stockbroker, volunteer. I ignored how others saw me after my conviction: as someone who created victims. That denial led to arrogance. I thought a minimum wage job was beneath me. It wasn't until I landed in federal prison—and later worked in a halfway house for $15 an hour—that I finally understood: all work is honorable. The sooner you accept that, the better your outcome.

Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern. Learn how to rebuild the right way.

A former physician home from federal prison wanted to write the Financial Litigation Unit (FLU) to settle millions in restitution for pennies. I warned him not to. He did it anyway. The response? Not only did FLU reject the offer—they asked for updated financials and flagged his available cash. Now they're watching him closer than ever. The idea that the government casually settles massive restitution is a fantasy inmates pass around daily. It's not true.

Don't poke the bear. Deal with restitution realistically. Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern for straight answers that save you pain.

A defendant called the night before sentencing, proud of his 12-page letter. But he hadn't done the work. For two years, no effort to fix the damage—no restitution, no remorse shown through action. Judges like Boo and Bennett say it clearly: don't just apologize—show what you've done to repair the harm. A letter can't replace a record of real progress. Judges trust patterns, not last-minute sales pitches.

Want a better outcome? Start early. Mitigate with evidence, not just words. Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern to learn how.

When I met a physician in Tampa facing a probation interview, he kept saying, "I didn't have bad intentions." But intent doesn't carry much weight when you broke the law and kept doing it for two years. What mattered more was that he finally owned it—clearly and directly. That shift, along with other mitigation efforts, led his probation officer to recommend a shorter sentence due to his extraordinary acceptance of responsibility.

📌 Real takeaway: Telling the unfiltered truth can influence your outcome.

👉 Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern. Learn how to prepare the right way.

Boredom—not violence—is often the biggest threat in federal prison. And boredom drives people to gamble, even those who swore they never would. It starts with a friendly card game and ends with debts you can't pay. When you owe money inside, there's no delay in collection—just pressure, threats, and escalating consequences. One missed payment can put your safety and sentence at risk.

Stay sharp. Don't let boredom turn into bad decisions. Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern for practical strategies to avoid unnecessary prison risks.

Simplify Before Federal Prison—And After

A billionaire in our community, heading to federal prison, asked for advice. He admitted he lost sight of the values that once drove his success. I told him to follow what Thoreau wrote in 1854: Simplify, simplify. In prison, you can spend thousands a month—but why? Spend less. Need less. Say no to distractions. Use this time to strip away the noise and reconnect with what matters. Simplification isn't punishment—it's a reset. And it might be the best preparation for what comes next.

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A physician expected two years in federal prison—the mandatory minimum for aggravated identity theft. But he didn't prepare. He didn't consider how victim statements might influence the judge. At sentencing, those victims spoke about ruined credit, unpaid bills, and emotional distress. The judge gave him four years instead of two. Why? Because he assumed the outcome and ignored the emotional toll on his victims.

If you're facing sentencing, put yourself in the victim's shoes. Start there. Join our weekly webinar every Monday at 1PM Pacific / 4PM Eastern to prepare the right way.