Scalable Randomness

When I first read Nassim Nicholas Taleb’s The Black Swan, I thought about the ways his teaching related to the time I served in prison. He offered lessons about life’s unpredictability. In the book, Taleb explains a concept called "scalable randomness"—the idea that unexpected, rare events (what he calls Black Swans) could completely transform the trajectory of our lives. These events often seem to occur out of the blue, but their impact is massive and lasting.

This concept reminded me about the unpredictability of life in prison. No one knew what would happen. All we could do would be to prepare ourselves for success, as we defined success. I wrote about that extensively in our course, The Straight-A Guide. If a person wants the highest level of liberty at the soonest possible time, the person should work exceptionally hard, figuring out the little steps he can take each day.

Thanks to lessons I learned from leaders, I realized early that even amidst the uncertainty and volatility of a high-security penitentiary, there were things I could control. I couldn’t predict perfect outcomes, but I could prepare for opportunities to capitalize on valuable moments when they came. This foundational mindset helped me transform my trajectory while I served decades inside.

Anyone can apply this strategy of scalable randomness to overcome adversity and advance prospects for long-term success.

Here’s how I did it and how you can, too.

Acting as the CEO of Your Life

One of the most important strategies I embraced in prison was thinking of myself as the CEO of my life. CEOs don’t wait for luck to come their way. They take calculated risks, build strong networks, and make proactive decisions to turn challenges into opportunities.

Like a CEO assembling a board of directors, I knew I needed to surround myself with mentors, even if prison walls physically separated us. I didn’t have the luxury of attending networking events or professional conferences. Instead, I found alternative ways to build the relationships that would become critical to my success.

The Founder's page of PrisonProfessors.org offers many examples of people who came into my life. Take a look at Norval Morris, a prominent law professor and author from the University of Chicago. His book, The Future of Imprisonment, had a huge impact on me, because he wrote about the concept of earning incremental levels of liberty through merit. I saw its insights as a guide not only for navigating prison constructively but also for advocating for meaningful change within the system.

After reading his book, I wrote an unsolicited letter to Professor Morris. In the letter, I shared how his work inspired me and outlined the ways I would apply his ideas to my adjustment inside. At first, I didn’t hear back. Weeks turned into months, and I could have easily resigned myself to the silence.

But here’s where scalable randomness played a huge role.

Eventually, Professor Morris replied. His response had a huge, life-changing influence on my life. He became a mentor, an advocate, and one of the first members of my board of directors. His influence opened doors for me within the prison system and beyond, granting me credibility with prison officials and others who helped shape my path.

This is the essence of scalable randomness. You can’t always predict when opportunities will arise, but you can position yourself to maximize their potential when they do.

Preparing Yourself for Positive Black Swans

Life will always present moments of randomness, moments you can’t control. But what you can control is your readiness to seize those moments. Here’s how to methodically prepare yourself to benefit from scalable randomness:

Invest in Personal Growth

I knew that if I wanted people like Professor Morris to take me seriously, I needed to demonstrate that I was actively working on becoming a better version of myself. That meant committing to education, self-discipline, and personal development.

Whether it’s through reading, taking online courses, or enhancing your professional skills, the best investment you can make is in your own growth. This doesn’t just build your capabilities; it also makes you a credible figure others are more likely to support. It's the reason we created Prison Professors Talent. We want to provide people in prison with a platform that they can use to showcase why they're worthy of support.

Reach Out Boldly

Don’t be afraid to take the first step, even if it feels intimidating. When I wrote to Professor Morris, I didn’t know if he’d reply. All I knew was that nothing would’ve happened if I didn't take the initiative.

• Identify people whose work inspires you.
• Draft a thoughtful message or letter that explains how their ideas have shaped your perspective.
• Express genuine gratitude for their influence.
• Even if you don’t hear back immediately, persistence can make all the difference.

Stay Resilient and Patient

Opportunities often take time to materialize. Months passed before I received a response from Professor Morris. But I understood that every attempt to connect had potential, even if the results weren’t immediate.

• Keep planting seeds, knowing that some will grow when the time is right.

Build Credibility Through Action

Words alone don’t make an impact. We need to take consistent actions to show our authenticity. I worked relentlessly to maintain discipline, build knowledge, and contribute positively wherever I could. These actions spoke louder than anything I could say about my intentions. When opportunities arose, people could see I was prepared to capitalize on them.

Adopt a Long-Term Mindset

Success isn’t instant. When working toward personal growth, building connections, or pursuing opportunities, think in terms of years, not days. The most meaningful transformations happen gradually.

Turning Challenges into Opportunities

You may be facing hurdles today, whether it’s navigating life after incarceration, rebuilding financial security, or adjusting to other significant changes. These challenges can feel overwhelming, but they are also fertile ground for growth and transformation. The lessons from scalable randomness reinforce this truth: even when everything feels uncertain, there are still steps you can take to create favorable conditions for success.

Your task isn’t to predict every positive outcome, but to maintain steady progress, positioning yourself to recognize and seize opportunities when they appear. I encourage you to document your efforts in a central location, such as a profile you can develop on Prison Professors Talent.

Action Steps

Start creating your own positive Black Swans with these steps:

• Set clear goals: Define success on your terms and envision the steps required to get there.
• Commit to lifelong learning: Whether through books, courses, or mentors, continuously expand your knowledge and skills.
• Network with intention: Seek out relationships that can add value to your life and be willing to reciprocate that value.
• Track your progress: Regularly evaluate your actions to ensure they align with your goals.
• Celebrate resilience: Recognize the times you’ve persevered through hardship. Use those moments to fuel your motivation moving forward.

Reflect and Act

Ask yourself:

• What skills or knowledge can I start building today to enhance my credibility and potential?
• Who are the people (authors, mentors, professionals) whose insights inspire me? How can I reach out to them?
• What specific actions can I take this week to position myself for future opportunities?

Final Thoughts

Success often comes from unlikely, unpredictable moments. But those moments are rarely accidents. By taking control of what you can—your mindset, your development, and your preparedness—you set the stage for those rare, life-changing opportunities to find you.

I’ve seen firsthand how resilience, persistence, and strategic action can transform lives, no matter the circumstances. You have the power to turn adversity into opportunity. Start now, and when your scalability moment appears, you’ll be ready.

Remember, you’re the CEO of your life. Build your board of directors, invest in yourself, and prepare for the Black Swans ahead.

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