The Black Swan

It's never too early and never too late to start preparing for a better life. I got this message after a jury convicted me, but before a judge sentenced me to serve 45 years in federal prison. My name is Michael Santos. I'd like others to consider the importance of preparing for success at the earliest possible time, sharing lessons that I learned from a book I recently finished. I listened to the Audible version of the book, and I highly recommend it.

Before getting into the lessons that apply to people who've been sentenced, I'll offer a structured "book report," using the same style that I teach in our various courses:

1. I'll describe the reasons I read The Black Swan by Nassim Nicholas Taleb.
2. I'll reveal what I read from reading The Black Swan by Nassim Nicholas Taleb.
3. I'll describe how The Black Swan by Nassim Nicholas Taleb relates to my work.

Then, I'll offer some insight into how you can use these lessons to begin sowing seeds for the best outcome in your life.

Why I Chose to Read The Black Swan:

I decided to read The Black Swan, by Nassim Nicholas Taleb, after hearing about it in another book, Never Split the Difference by former FBI agent Chris Voss. My friend Justin Paperny recommended the book by Voss, and it intrigued me. When I heard the author recommend Taleb’s work, I thought it might be another resource that would teach me ways to deal with the challenges I face in building my business. Over the years, I’ve learned the value of seeking wisdom from people with life experiences different from my own—people who can teach lessons about preparing for the unexpected.

In my youth, I made reckless choices and committed crimes, never imagining I would end up in prison. But during the 26 years I served, I gained a profound understanding of the importance of strategic preparation, resilience, and adaptability. These concepts became central to the self-directed courses I’ve created, and they continue to guide me in my advocacy work today.

Nassim Taleb’s The Black Swan discusses rare, unpredictable events and he theorizes on how they shape our lives. Taleb's insights seemed like a worthwhile investment of my time, so I listened to The Black Swan during my runs, eager to deepen my understanding of navigating uncertainty. The lessons resonated with my own journey, reminding me of how preparation and adaptability helped me persevere through prison and continue to shape my work helping others today.

What I Learned from Reading The Black Swan:

Taleb argues that the most influential events in history and our personal lives are often unpredictable, massively impactful, and rationalized in hindsight. These "Black Swan" events—such as financial crashes, technological breakthroughs, or life-altering personal setbacks—illustrate the fragility of our assumptions about predictability.

From The Black Swan, I took away three critical insights:

The Illusion of Predictability:

Human beings often mistakenly believe they can predict the future based on past experiences. The author builds a great case to show how Black Swan events defy conventional forecasting methods. Recognizing this illusion helps build humility and preparedness for unforeseen challenges.

Resilience and Adaptability:

The pursuit of success requires us to expect Black Swans. We must prepare ourselves to deal with them, and figure out ways to adapt. The art of resilience means creating systems and habits—like continual learning, maintaining a disciplined mindset, and nurturing meaningful relationships—that position us to respond effectively when unexpected opportunities or adversities arise.

Anti fragility:

Taleb introduces the concept of anti fragility—systems or individuals that not only survive stressors, but become stronger because of them. Reflecting on my incarceration, I can see the relationship between decisions I made early in my term related to success much later. We have opportunity costs with every decision we make. By pursuing an education, learning how to write, and developing strategic relationships helped me build confidence. That strategy helped me cope with adversity, and used it as a catalyst for personal and professional growth.

How The Black Swan Influences My Prospects for Success:

The Black Swan reinforces the strategies I teach in every self-directed course. It emphasizes that thorough preparation and adaptability matter far more than specific predictions about the future. By embracing uncertainty as a natural element of life, I can guide others to:

• Create Flexible Plans: Encourage the development of adaptable strategies that can be adjusted rapidly when unforeseen opportunities or setbacks emerge.
• Invest in Continuous Learning: Promote lifelong education and self-improvement as a primary means to stay anti fragile.
• Build Diverse Networks: Strengthen relationships and connections to enhance resilience, creating a support system prepared to respond collectively and constructively to unexpected challenges.

Ultimately, The Black Swan aligns perfectly with my life's work: preparing others, especially those impacted by the justice system, to overcome adversity by developing robust, resilient, and anti-fragile lives. By expecting the unexpected, we transform every challenge into a catalyst for growth and achievement.

Begin Building Today

To those recently faced sentencing, I want to offer both guidance and a challenge. Consider this a new chapter in your life. Start writing about the person you're going to become. The choices you make now will shape the opportunities you encounter later. Regardless of where you're starting from, prepare for excellence while anticipating many, many black swan events. Challenges are in your future. It's your job to prepare.

Through all my work, I make three promises:

1. I'll never lie to you,
2. I'll never ask you to do anything I don't do, and
3. I'll never charge you a penny for any information on Prison Professors.

If you've recently been sentenced, you should expect to find many obstacles and obstructions in your future. The people who work in prisons consider themselves accountable to the judge who sentenced you, and they may want to see you serve the full sentence. You must build a body of work, a personal story, that shows you're worthy of relief.

Consider the following questions:

1. Why are you worthy of a higher level of liberty?
2. What have you learned from this experience?
3. In what ways does your work advance you as a candidate for leniency?
4. How do you anticipate stakeholders will view you?
5. What case can you make for clemency, or administrative relief?

If you lack formal education or feel left behind academically, get started, as I did. I was in a solitary cell when I read the work of great authors. They taught me to think differently and start investing in myself. You can start learning today.

Begin by dedicating yourself to reading every day. Start with simple materials if you must, and work your way up. Use a dictionary, expand your vocabulary, and improve your comprehension. Writing is equally important—practice by journaling, drafting letters, or even reflecting on your thoughts each day. Build a profile on Prison Professors Talent and develop it. Seek out others who can teach you, exchange ideas, and build on their knowledge. Education requires a commitment to lifelong learning.

If you’ve already achieved academic or career success in your past, your work is not done. That foundation is valuable, but you must now be creative.

• What can you contribute to the world, given the changed circumstances of your life?

Build a new body of work. Think strategically about how to use your skills, whether it’s writing a book, developing an idea, or contributing to a larger community effort. Position yourself as a candidate for relief by demonstrating your growth, leadership, and commitment to being a force for good. You must expect obstacles, and still architect the blueprint for your future.

Above all, never be surprised by black swan events—the chaotic, unpredictable moments that can shake the ground beneath you. Anticipate them, prepare for them, and understand that resilience is your responsibility to develop. Build a mindset that allows you to adapt and thrive, no matter the circumstances. Take ownership and empower yourself to rise beyond the external forces that influence your life today. And always remember that more opportunities exist in the future than in the past.

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