Predicting the Future

When serving decades in prison, I came to understand that success is built on planning, resilience, and disciplined execution. This understanding allowed me to turn what could’ve been a life of despair into one of growth, contribution, and eventual financial independence. But along the way, I also learned that we are not as good at predicting the future as we might think. I'll always remember a quote by Yogi Berra:

The future ain't what it used to be.

I got more insight while listening to Nassim Nicholas Taleb's book, The Black Swan, has shaped the way I approach planning and goal-setting. I think anyone can learn from great books.

Taleb’s concepts on predictions remind us to rethink how we plan for the future. Life is full of unforeseen events. While some might view this uncertainty as a threat, I see it as an opportunity to build strength, adapt, and thrive in unexpected circumstances. Today, I want to offer some insight into the value of predictions, the pitfalls of overconfidence, and how you can harness uncertainty to create a better future.

Why Predictions Matter—but Not in the Way You Think

Predictions often provide a sense of reassurance. As a Bitcoiner, I frequently follow individuals who share their forecasts on Bitcoin's future price. It’s comforting to read projections suggesting Bitcoin will hit specific values within the next three, six, or twelve months. However, as an investor, my perspective is much more long-term. As CZ aptly noted, short-term predictions are notoriously difficult, but looking ahead—three, five, or even ten years—offers greater clarity.

We feel in control when we believe we can anticipate what’s coming. But as Taleb highlights in The Black Swan, humans are inherently poor at predicting rare, impactful events. These “Black Swans”—events like financial crashes, technological breakthroughs, or even personal crises like losing a job or facing incarceration—are unpredictable, yet they drastically shape our lives.

Looking back on my prison experience, I realize that a rigid reliance on predictions would have done more harm than good. I couldn’t predict the challenges that lay ahead or the opportunities that might arise. What I could do, however, was prepare myself for uncertainty. I had to create a framework of resilience and adaptability that allowed me to face whatever came my way. That mindset transformed my time in prison from 26 years lost to 26 years invested in strategic personal growth.

Common Pitfalls of Predictions

Taleb outlines several reasons why predictions often fail us. These insights aligh with my own experiences and they also harmonize with what we cover in our Straight-A Guide lessons. They can serve as a guide for you, whether you're navigating challenges in the justice system, rebuilding your life post-adversity, or striving to achieve personal growth.

Overconfidence in Our Predictive Abilities

We often believe we can predict the future with accuracy, especially if we base our forecasts on past patterns. For instance, you might think, “The market has always bounced back; it will again,” or “I’ve always struggled; it will always be that way.”

Despite selling cocaine during the recklessness of youth, it never occurred to me that I'd serve time in prison. When I entered prison, it would’ve been easy to predict a bleak future. After all, the data on recidivism and limited opportunities for formerly incarcerated individuals painted a grim picture. But by challenging that narrative, I focused on preparing for success, not a prediction of failure.

The Narrative Fallacy

Humans love creating stories to explain the world. We simplify complexities by stitching together past events into neat narratives. But real life isn’t always neat. This narrative fallacy can make us believe the future will follow the same logical progression as the past.

I’ve seen many people in prison fall into this trap. They resign themselves to the idea that they’re destined to fail because they’ve failed before. But your past doesn’t have to dictate your future. The key is to stop writing the same story and start building a new one.

Limits of Historical Data

Historical data has its limits. Just because something hasn’t happened before doesn’t mean it never will. In Earning Freedom, I reflected on how the world shifted in unexpected ways during my time in prison. For instance, during my youth, tensions with the Soviet Union were a constant concern. Yet, early in my sentence, President Reagan and Russia's leader forged an unlikely friendship, transforming adversaries into allies. This taught me an essential truth: the present is no guarantee of the future. What exists today can change in ways we might never foresee.

When I prepared for my release, I knew I had to think beyond what I’d seen or experienced in the past. I focused on what was possible, not what was probable.

The idea of using the experiences I gained in prison as a launching point for a career in advocacy seemed improbable, but it wasn’t impossible. By focusing on preparation and adaptability, I created a future that wasn’t bound by my past.

Turning Uncertainty into Strength

Instead of trying to predict every outcome, Taleb encourages us to focus on being resilient and able to adapt when we encounter Black Swan events. This principle aligns perfectly with the strategies I developed in prison through our lessons on the Straight-A Guide.

Start with a Vision

Regardless of what lies ahead, get clarity by defining success. Pursue what you want to achieve. If you know what you want your life to look like, you can reverse engineer the path to get there.

While serving my sentence, I had a clear vision: I wanted to emerge from prison stronger, wiser, and better equipped for success. I wanted to be able to put on a suit and tie and walk into any room, confident that I could open any opportunity. That vision guided every decision I made, from the books I read to the relationships I built.

Create a Plan—but Stay Flexible

A plan is essential, but it’s equally important to adapt when circumstances change. For example, I focused on education while in prison, even though I couldn’t predict exactly how it would pay off. That investment in myself gave me the flexibility to seize opportunities when they came my way after release.

Prepare for Uncertainty

Rather than fear what you can’t control, strengthen your ability to respond. This means limiting vulnerabilities and diversifying your options. For instance, when I entered the world of entrepreneurship post-prison, I took calculated risks without putting all my resources into one strategy. I embraced learning across multiple domains, from writing books to building Prison Professors.

Actionable Takeaways for Resilience and Growth

1. Build Your Knowledge Base: Invest in lifelong learning. Read widely, attend webinars, and develop skills that make you versatile and prepared for opportunities.

2. Challenge Your Assumptions: Reflect on your own biases about the future. Are you too confident in a specific outcome? Are you clinging to unhelpful narratives about your past?

3. Focus on What You Can Control: You can’t control Black Swan events, but you can control how prepared you are. Focus on daily habits, education, and relationships that strengthen you.

4. Think in Probabilities, Not Certainties: When making decisions, weigh the potential risks and rewards instead of assuming a single outcome.

5. Seek Mentorship: Surround yourself with mentors and advisors who challenge your thinking and help you see new possibilities.

Questions for Self-Reflection

• What’s one area of your life where you're relying too heavily on predictions?
• How can you start preparing for uncertainty instead of fearing it?
• What daily habits can you adopt now to build resilience and adaptability?

Final Thoughts

Whether you’re rebuilding your life after adversity, navigating a career change, or striving for personal growth, the value of predictions lies not in their accuracy but in how they drive us to prepare and act. Take it from someone who spent 26 years in prison learning this lesson firsthand: you can’t predict every challenge, but you can prepare for all possibilities.

Your future isn’t written yet. It’s built through vision, planning, and disciplined action. Start now, and remember this truth from The Black Swan: uncertainty isn’t your enemy. It’s your chance to rise.

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