The Risk That Was Worth Taking

Playing it safe is the quickest way to stay stagnant. For me, the leap that changed everything came after 20 years of building a comfortable, successful career across healthcare, finance, and laboratory services. At the height of the pandemic, I walked away from that comfort zone to dive into clean energy with Tangelic. Leaving decades of familiarity behind to bring reliable power to underserved regions was a massive risk, but true leadership requires trade-offs. That single choice took me on a mission to Ghana to drive the Sunrise Spectrum Initiative. Because I took that risk, we aren't just discussing impact; we are actively changing lives on the ground.

One of the biggest risks I ever took was choosing to step away from the security of a long career in government contracting and fully pursue the work I believed I was called to do.

For nearly 20 years, I had the stability of a professional career, leadership responsibilities, and the opportunity to support projects connected to NASA's Jet Propulsion Laboratory. It was a tremendous experience, but over time I realized that my purpose was pulling me in another direction. I felt called to spend more of my life developing people, speaking, training, pastoring, teaching, and serving communities that often needed encouragement, leadership, and hope.

That calling eventually took me beyond traditional professional environments. It meant stepping into communities, correctional institutions, and prisons not just as a trainer, but also as a pastor and someone committed to helping people understand that their current circumstances did not have to define their future. Serving incarcerated individuals, correctional professionals, law enforcement officers, and people in the community became an important part of that journey.

Walking away from something stable was not an easy decision. There is always uncertainty when you leave what is familiar to pursue what you believe you are called to do. But I reached a point where playing it safe would have meant ignoring that calling.

"Sometimes the greatest risk is not stepping out. It is staying where you are after you know you have been called to move." Charles Myles

That decision led me to build Powerful Days and expand my work as a speaker, trainer, pastor, and community leader. It opened doors for me to serve people in environments I could not have imagined earlier in my career.

The risk did not eliminate every challenge, but it brought greater alignment between my work and my purpose. Taking that leap allowed me to build a life centered on helping people grow, lead, heal, and transform.

The biggest risk I ever took was moving to Austin with almost nothing and betting on myself before I had any evidence that the bet would work.

I didn't have a college degree. I didn't have a career mapped out. I didn't have a safety net. What I did have was a strong belief that I was capable of more than the circumstances around me suggested.

At one point, I had very little money left. I remember eating popcorn as a meal because it was what I could afford.

Then Dell gave me an opportunity.

It was an entry-level small-business sales position paying $14 an hour.

I could have looked at the number and decided it wasn't enough. Instead, I looked at the opportunity.

I went all in.

I made roughly 200 outbound calls a day. I wore a suit every day. I studied technology, studied the business, learned how customers made decisions, and became obsessed with getting better.

That decision completely changed the trajectory of my career.

What started in small-business sales eventually took me into engineering, data center technology, cybersecurity, and back into technology sales. I built relationships with executives and technical leaders, learned how to operate on both sides of the table, and eventually built businesses of my own.

The risk wasn't taking the job.

The risk was believing in myself before anyone else had a reason to.

That has become one of the defining principles of my career. I don't need to have the entire path figured out before I take the next step. I need to recognize the opportunity, prepare myself for it, and have the courage to walk through the door.

That $14-an-hour job didn't look like much at the time.

It turned out to be the beginning of everything.

I needed feedback and validity. I took my first game straight to one of the largest game conventions in the US, GenCon. It was a ton of work but worth every second of it. The feedback we received helped turn the game into what it is today. The risk was spending a ton of money to get no one interested in playing. However we had nearly 100 people playtest the game. We were the most played game that weekend in the test hall, and we got featured in Gaming Trends webzine in the cover spot!

Completing 75 Hard was one of the clearest examples of discipline and commitment in my life. The challenge required me to be consistent every day, regardless of how busy I was, how tired I was, or how much I wanted to make an excuse. It pushed me to develop a greater level of discipline and taught me that progress comes from doing the things you committed to doing, especially on the days when you don't feel like doing them.

But completing it wasn't something I did alone. My wife played a huge role in making it possible. We had a small child at the time, which meant that the time and energy required to complete the challenge didn't just come from me. My workouts, schedule, and commitments affected our entire family. My wife supported me, helped make space for the things I had committed to, and carried additional responsibilities when I needed the time to follow through. Her support and willingness to sacrifice alongside me were a major part of my ability to finish.

The experience also taught me that discipline isn't always an individual pursuit. The commitments we make for ourselves can affect the people we love, and having a supportive partner makes a tremendous difference. It gave me an even greater appreciation for my wife and for everything she does to support me and our family.

More importantly, I became a better version of myself because of the experience. I learned that I am capable of doing difficult things consistently, even when circumstances aren't perfect. I developed more confidence in my ability to follow through, became more intentional with my time, and strengthened my understanding of what discipline really means.

75 Hard wasn't just about completing a 75-day challenge. It reinforced a mindset I want to carry into every area of my life: make a commitment, do the work, stay consistent, and don't quit simply because something becomes difficult. The challenge ended, but the discipline and lessons I gained from it continue to influence the way I approach my work, my family, my faith, and my personal growth.

Early in my career, playing it safe looked like sticking strictly to established frameworks where success was predictable, controlled, and low-risk. I realized that comfort is often the quiet enemy of meaningful scale.

My defining leap came when I decided to step outside the safe boundaries of standard corporate predictability to commit fully to building new ventures from the ground up expanding into unfamiliar operational territories and championing initiatives where there was no blueprint to follow.

What made me take the risk was a fundamental shift in perspective: the true risk wasn't failing at something new; it was remaining comfortable while my full potential and vision went unrealized. I saw an opportunity to bridge strategic execution with real community and business value, and I knew that waiting for 'perfect timing' was just procrastination in disguise.

Taking that leap changed everything. It forced me to sharpen my strategic agility, build resilience, and move from being a manager of processes to a driver of transformational growth. Beyond the tangible outcomes expanding our operational reach and launching successful initiatives it fundamentally redefined how I lead. It proved that real authority in leadership isn't granted by safety; it's forged by stepping into uncertainty and executing anyway.

For years my win was nine doors in Fayetteville. Cash flowing, paid down, safe. Then I sat across from a billionaire who told me to sell them all and learn to raise capital, because I was built for more than nine doors.

Selling what you worked a decade to build feels like betrayal. But I realized playing it safe was its own generational curse. My family taught me to hold on to what you have. Nobody taught me to trade a good thing for a great one.

So I took the leap. I'm selling the portfolio, rolling it forward, and building toward apartment buildings, with a goal of 10,000 doors. In the same season I founded Patrick Capital Group, published The Black Sheep Blueprint, and started teaching first-generation wealth builders every week.

What happened because I did? I stopped being the guy with rentals and became the guy who breaks the cycle out loud. The risk wasn't losing the properties. The risk was dying with a vision still in me.

I've never played it safe a day in my life, but joining the Army was the decision that changed my life the most.

At 23, I'd been moving from job to job and was driving over-the-road for Schneider. I'd listen to stories on the radio about 18- and 19-year-old kids going to Iraq and getting blown up. I wasn't much older, but I kept thinking that I wasn't doing a whole lot with my life. If I could take a slot and spare even one of those kids, that would count for something.

That was why I enlisted. It led me from the infantry to becoming a pilot and eventually a technologist. Twenty years later, that path has brought me to platform engineering at Defense Unicorns.

My reason for joining reminds me of the story about a man throwing stranded starfish back into the ocean. Someone asks how he can possibly make a difference when the beach is covered with them. He picks up another, throws it back, and says, "I made a difference to that one."

I couldn't know what difference I would make when I joined. But I wanted to try.

I've taken quite a few leaps of faith in my life, beginning when I was 18 years old, selling handmade scrimshaw jewelry on the streets of Harvard Square. But perhaps the most meaningful was my decision to invest in the revitalization of the historic waterfront in New Bedford, Massachusetts.

By 2006, I had built Cardoza's Wine & Spirits into a successful regional business. I could have continued doing what I knew, enjoying the security of an established company. Instead, I invested more than $650,000 to transform a 170-year-old building at 90 Front Street into Cork Wine & Tapas Bar, right in the heart of the New Bedford Whaling National Historical Park.

At the time, the waterfront had tremendous history and character, but much of its potential remained unrealized. I believed that if we created something truly special something that brought people together and gave them a reason to rediscover downtown others would follow.

It wasn't just about opening a restaurant. It was about helping bring a historic neighborhood back to life.

And that's exactly what began to happen.

In 2009, the New Bedford Economic Development Council honored Cork with its Impact Award. Matthew Morrissey of the council credited the project with helping inspire other investments in the surrounding downtown and setting a higher standard for historic preservation and customer service.

That recognition meant more to me than simply having another successful business. It was confirmation that taking a risk for something you believe in can create opportunities far beyond your own front door.

Of course, not every leap I've taken has ended the way I expected. I've experienced tremendous success, financial setbacks, and more than one complete reinvention. But those experiences taught me that playing it safe can sometimes be the greatest risk of all because you may never discover what you're capable of accomplishing.

Today, approaching my 70th birthday, I'm taking another leap with Postcards from Tahoe and The Tahoe Bracelet Company. Both are built around a simple idea: create beautiful products that bring people joy while helping protect the extraordinary natural environment of Lake Tahoe and support the people who call it home.

I suppose the common thread throughout my life has been this: I've never been particularly interested in building a business just to make money. I've always been more excited about what a business can make possible for other people.

My philosophy is simple: Be kind and have fun. And when you have an opportunity to do something meaningful, don't be afraid to take the leap.

The leap that changed everything for me was deciding to take ownership of my future as a filmmaker. I had spent 24 years in the Navy, where I understood the structure, the expectations, and what it took to lead. Pursuing filmmaking meant becoming a beginner again and putting my ideas in front of people who might not see what I saw.

Writing had been part of my life during my military career. At one point, I had to choose between pursuing it and continuing my service. I chose the Navy, but the desire to tell stories stayed with me. After retiring, I began moving toward screenwriting and filmmaking.

What pushed me to take the risk was realizing how much of my creative future I was leaving in other people's hands. I watched documentaries and interviews with directors I admired, and the message I kept hearing was simple: if you want to make films, start making them. I wanted to understand the entire process so I could give my stories a chance to exist.

That decision led me to establish Woodson's World Studios and develop my skills in writing, producing, directing, cinematography, and editing. It also led to projects such as URNS and A Clean Past, through which I've continued developing my voice as a spiritual and psychological storyteller.

The biggest change was in how I saw myself. I began treating my creative ambitions as responsibilities that required action. There were skills to learn, mistakes to work through, and projects to finish. Taking that leap gave me the opportunity to build a body of work and the confidence to keep going.

My blueprint is to prepare, take the first step, and keep learning as you move forward. Faith has helped me trust the journey; consistency has helped me do the work.