Erin Wicomb

Why Do We Fall?  The first time I was arrested and transferred to the Tombs in downtown Manhattan, I was met with the harsh reality of a place that seemed designed to bury not just bodies, but hope. The Tombs, as it’s infamously known, is a New York City jail, its nickname coming from its resemblance to Egyptian burial tombs. One of the most jarring moments was crossing the “Bridge of Sorrows.” This narrow, suspended walkway gave prisoners a fleeting view of the outside world. For a second — and just a second — I was no longer an inmate but a man, seeing the city that had once pulsed with life and opportunity all around me. But before I could grasp it, the world I had known disappeared again, replaced by cold steel and concrete, where time was no longer a guarantee, and freedom was a distant dream with no deadline. The experience was agonizing, especially as I still fought for my innocence.   I was a businessman caught in the crossfire of a white-collar real estate investment ...

No Arms, No Legs—No Excuses This story has been one of my greatest life hacks. It’s what I remember whenever I’m in a funk or feel like I'm facing something I can't overcome. I think about this story regularly, especially now as I conquer this current obstacle in my life.  It pulls me out of self-pity and reminds of what’s possible, no matter how insurmountable things seem. I grew up swimming competitively and swam provincial, which in South Africa is equivalent to swimming for the state team. My mom would wake me at 5 AM to hit the pool before school from 5:30 -7 AM, and I’d be back in the water after class from 4-6 PM. Swimming was my life. But by the time I moved to the U.S., swimming took a back burner to business and entrepreneurship, though I still jumped in the water whenever I could. The day that changed everything: Years  later, while I was living in San Diego, my old friend Julz—who was visiting from South Africa—invited me to join her in a long-d...

Building Muscle and Brains: A Journey of Continuous Growth There’s often a myth that people who are incarcerated have endless time to work out, read, and improve themselves. But the reality is, whether inside or outside, time remains constant. It’s not about having more time; it’s about how you prioritize the time you have. Just like anyone on the outside, it’s easy to get sucked into distractions—endless TV, gambling, or unhealthy eating. But the desire to be smarter or fitter isn’t just a fleeting goal for most of us—it’s an ongoing process, a lifestyle. In my early 20s, I was significantly overweight and unhealthy. I wasn’t just behind in terms of fitness—I was also often clueless in conversations, lagging behind my peers in knowledge and life experience. But through consistent effort and discipline, I made a change. Now, I’m in one of the best shapes of my life, both physically and mentally. Here’s how I built muscle and brains along the way. 1. Know Where You Are • Fitness: I ...

 Bastian’s Best Lessons During my current coast-to-coast tour of New York and California’s jail and prison systems, I’ve had the opportunity to share some of the hard-earned lessons I’ve gathered over the years with men from various walks of life. This past weekend, I gave a speech to both the inmate workers and staff, not necessarily sharing my personal experiences, but rather the wisdom of one of the sheriffs who has spent the last 20 months managing 120+ inmate workers. Having been incarcerated for nearly four years, I can say I’ve rarely witnessed the level of compassion and dedication this sheriff has shown. He wasn’t just focused on maintaining order—he genuinely wanted to help these men become better versions of themselves. Below are some of the key lessons he imparted, expanded with context from my own observations. Bastian’s Best Lessons: 1. Real men cry. Showing emotion isn’t a sign of weakness—it’s a sign that you care. Real men face their emotions and work through t...

Boofing Knowledge Entering the prison system—or having a loved one who does—introduces you to a whole new world of vocabulary you never expected to learn. You encounter people from walks of life so different from your own that you almost feel like you’re in a bizarre, twisted reality show. My time at Riker's Island, the notorious prison known for its violence, neglect, and all-around human degradation, was no exception. I was a fresh fish, trying to keep to myself, my nose buried in any book I could get my hands on. At the time, I was reading Long Walk to Freedom , Nelson Mandela’s autobiography—a man who spent 27 years in prison fighting for racial equality in my homeland, South Africa. One of his quotes struck me deeply: “You don’t truly know the people of a nation until you know those who are in prison.” Before my own incarceration, I naively viewed prisoners as just criminals. But that was before I really understood how the so-call “justice” system works and how easily freedom ...

Planes, Ships, and Horses: Navigating Life’s Journey I’m currently studying to get my pilot license, and let me tell you—it’s no walk in the park. But if there’s one thing I’ve realized, it’s that planes aren’t meant to stay grounded. They’re built to soar. Just like ships aren’t designed to sit safely in the harbor. Ships are made to brave the open seas, to navigate through storms and unpredictable waters. These days, technology makes it easier to fly solo, with autopilot systems and electronic aids smoothing the way. But here’s the thing—just because you can fly alone doesn’t mean it’s the best way. When you’re learning to fly, having a co-pilot or instructor by your side is essential. They’re there to watch your blind spots, to help you navigate the challenges that no technology can fully anticipate. Relying solely on gadgets and self-study means missing out on the invaluable experience and wisdom that only a seasoned mentor can offer. Think about a ship. Sure, modern tech can help ...

Feedback Over Failure I am in prison. There’s no denying that when it comes to failure in life, it doesn’t get much worse than this. Even as I continue to fight for my innocence against my wrongful incarceration, I can’t escape the reality: my decisions and choices led me here. I take full responsibility for my life and the path I’ve taken, and I own every consequence of those decisions. But here’s the thing: getting disappointing results—whether it’s failing a test, bombing on a date, or losing out in business—doesn’t mean we are failures. It doesn’t mean we are worthless or that we’re not good enough. In fact, it’s quite the opposite. When we receive feedback, especially the kind we didn’t ask for, we should embrace it. Feedback, no matter how harsh, is a sign that we’re alive, that we’re taking action, that we’re in the game. The truth is, life will throw both good and bad feedback our way. And believe it or not, it’s the negative feedback we should welcome more. Why? Because it’s a...

The Myth of the “Self-Made Millionaire” The idea of a “self-made” millionaire is a deeply flawed myth. When someone claims that all their success, whether in sports or financial achievements, is solely due to their own efforts, it raises a significant red flag for me. There was a time in my life when I believed in fantastical notions like Santa Claus and Peter Pan. But just as I eventually understood the laws of gravity and the logistical impossibility of a toy factory at the North Pole, I also came to see the fallacy in the concept of a “self-made millionaire.” As a young adult, I was captivated by the idea that through sheer willpower, one could achieve financial success. By the age of 20, I had set a goal to become a “self-made millionaire” by 25. Raised by a single mother in South Africa, the obstacles seemed immense. Yet, after moving to the USA and establishing a real estate business, my net worth surpassed a million dollars within seven years. Despite this, after nearly two deca...