The day I decided to leave it all behind was surprisingly ordinary, yet it was the culmination of a journey that had taken me through various experiences. The usual hum of office chatter, the fluorescent lights that never seemed to dim, and the steady barrage of emails and deadlines were just the background noise to a life that felt increasingly meaningless. My parents had been trippy hippies, living on the fringes of society, living on and off a boat through my formative years, but I’d chosen a different path, one that seemed more reliable and stable—at least on the surface.
I always seemed to have a series of jobs from a young age. I cleaned the bottom of boats and painted the bottom of boats. There is nothing like being a pre-teen applying highly toxic substances in very credible death-defying tidal cradles in hypothermia-inducing cold waters at 3 in the morning on a school day. I worked as a barback, short order cook, waiter, gas pump jockey, retail associate, logger, mechanic, welder, and more. Until my junior year of high school, I hustled to make enough money to keep a car on the road. Take girls out on dates. Then I went professional.
My pseudo-professional journey started with the Army National Guard, where I learned discipline and gained a sense of camaraderie as an enlisted soldier driving tanks. But there was no route to a full-time job, so I transferred to the Marines to blow up tanks, seeking more challenge and excitement. The Marines tested me in ways I hadn’t anticipated, and I loved it—until the day a random accident left me with a broken neck and back. The despondent depression and fear of not being able to move. The loss of feeling and capability ate at my soul. The recovery was long and painful, but I pushed through it, refusing to let my injuries define me. However, the experience left me questioning my path. Was I truly on the right track?
After the Marines, I continued to serve in other ways. I became a tribal police officer and then a corrections officer in two different sheriff’s departments. These roles had unique challenges and dangers, and while I found them rewarding, they didn’t pay well. Law enforcement, protecting good people against bad people, and serving my community were important touchstones that wore away under the relenting pressure of bureaucracy and politics. It was all part of the same relentless grind. I gave my all to these jobs, working long hours and dealing with tough situations, but it felt like I was just another cog in a massive machine turning people into convicts with little to show for it.
I spent several meaningless years after leaving law enforcement doing just about anything, mostly legal. I worked as a photographer, an author, an executive assistant, a technical sales professional, and a consultant on physical and cyber security. I hustled to put money into my pocket. I ran huge technical programs that impacted the entire nation, only to see my efforts denigrated by supposedly experienced business professionals. During this time, I couldn’t hold a regular job because, amid all this hustle for cash, I got two bachelor’s degrees and a master’s degree. I slowly got better jobs that paid more but also demanded a chunk of my soul. The lifestyle led to my first divorce. Well, that and I’m a jerk. I hustled through pain. I learned a lot of hard lessons watching companies implode from arrogance and stupidity. I was on the ground floor of the dot-bomb. I knew things were wrong but didn’t have the knowledge, skills, or abilities to define them. I was a business mechanic, wondering what the engineers and architects of the companies were thinking. So I married a new woman and struggled through grit and determination to build something useful.
Seeking a change of pace, I became a university professor. Academia seemed like a haven where I could inspire young minds and find fulfillment. I could still serve but at the same time ponder the choices of life. But academia had its pressures—the pressure to publish, the constant academic politics, and the paltry salaries. It didn’t take long to realize that I had traded one grind for another. I was furious that what might bring meaning to my life was meaningless to academia. I was despondent that teaching others the skills to hold down a job was not even on the list of priorities of a professor.
I was still struggling to keep my head above water, but now I had the added pressure of molding young minds while trying to maintain a semblance of a personal life. I struggled to overcome the deadlock of academia’s pressures to do anything but teach. At the end of my academic career of getting grants or perish, I sucked as a professor, and though I got tenure early and I served in senior academic roles. I think academia is better off without me and the reality I might impart to students. I have honestly flirted with the idea of returning to academia, but each time I get close, there is some red flag waving like a blood-torn remnant in my path, warning me off.
All these jobs had one thing in common: they didn’t pay much, and they demanded a lot. I was stuck in a cycle of working hard, earning just enough to get by, and never feeling like I was progressing. It was the same story repeatedly—get a job, work hard, hope for a promotion, and maybe, just maybe, retire with enough money to enjoy a few years of freedom. It was exhausting, and I was ready for something different.
I moved from academia to government executive service again to try and make an impact on the nation—to do good. I joined an organization that positively impacted every American daily, which was meaningful to me. I was proud to be a silent guardian helping keep Americans safe in my own unique way. Except it was a grind, a slow destruction of my soul in a way that could only be explained as pain on parade. I left that job for another government job in the intelligence community. I took a job working for the worst agency, in the worst organization, in the worst climate, all according to their own Federal Employee Viewpoint Survey. I took the job willingly, knowingly, and with the idea I could change things. I was an insane prisoner of a system that pilfered my earnest enthusiasm and crushed my soul like wine grapes.
Fairly consistently throughout my career, I have often had the worst of the worst jobs. I was never hired like some fair-haired business nerd in an ivory tower, given opportunity and mentorship because of my parent’s role in running some trust fund. I struggled from one job to the next, building the instruments of other people’s profit. Grinding. Hustling. A circuitous route of pain-filled employment that was an opportunity because nobody they wanted to hire would ever take the job. My backwoods redneck hippy-dippy parents were a wage-grade civil servant father and a stay-at-home mom. They would look and see normal. Work hard and die young. They were the recipients of some of the greatest social and retirement programs in the history of the planet.
The day it all came crashing down, I was sitting in a conference room at my job as a senior executive in the intelligence community. I was responsible for securing the nation’s infrastructure, but the work felt like an endless treadmill of meetings, reports, and bureaucratic red tape. In every metric I could deploy to grade myself or others looked at me, I was wildly successful. Heck, I even managed to piss off the President of the United States personally. I looked around at my colleagues, playing the same game and chasing the same elusive dream, and realized I didn’t want to be part of it anymore.
I remembered my parents, who had rejected the consumerist lifestyle in favor of something simpler. At that point, they had nothing to show for it but thirty-plus years of retirement. I decided to follow their lead. I sold everything I owned, gave away what I couldn’t sell, and walked away from the traditional life of consumerism. My wife was all in on this as we were about to be empty nesters. I bought an old sailboat, spent months fixing it up, and moved aboard. It was a radical change, but it felt right. I was leaving behind the big house, the fancy cars, and the endless drive to earn and spend. Instead, I embraced a life of freedom and simplicity.
Anybody who has ever owned a boat is giggling at this point. A nearly 50-foot sailboat is where you spend money and hope it doesn’t sink when you live on it. It’s much more like keeping up a house when you are always there. A house you pick up in the air every few seconds and drop into an acidic bath called the ocean. It is much simpler. The boat is broken in some new way, and you don’t know it yet.
Even in this new life, I had to work. I took executive-level jobs that allowed me to work remotely, which paid well enough to support my new lifestyle. But the pay was always tied to my previous roles, a reminder that the corporate world was never far behind. It was just another example of the traps of the modern work model, where you could never truly escape the constant pressure to earn and achieve more. Companies cry foul at anti-competitive practices of government while employing anti-competitive practices against labor as a form of policy. Insert mad eye-rolling ironic gesture here.
A person who would later become my boss threw me a lifeline: Join his company, do good things, help him out, live on a sailboat, drive a convertible, and he’d never look at my timecard. Just make things better, is all he asked. So, we did that, and it was great for about two years. We grew the program, leaned in on ensuring it was cost-effective, and invested in the talent that made it amazing. I learned and taught people a lot, and I saw a slightly rosier picture of work and life balance for a few short years out of my entire career. That can’t be true for long.
Life is pain. It was simple. My wife and I were starting our new life together and working hard to make the dream a reality. A few months into the new job. She woke up in the middle of the night holding her chest and squeaked out in pain, “I think I’m having a heart attack.” This is my primarily vegan, marathon running, martial arts expert, yoga fiend, and clean-living wife. I rushed her to the emergency room. Why no ambulance? We lived on a boat. Trust me that is a series of antics you don’t want to consider. Luckily, she wasn’t having a heart attack. The bad news was she had a major lymphoma. A tumor the size of my fist in the center of her chest, squeezing her heart and lungs and growing fast. The next 18 months redefined pain and sacrifice with the loss of everything that made up her identity. She lived. Forever scarred and disabled. But she lived.
Then, the company went private equity from publicly traded. Then, there was the merger from hell. The merging, like cows and pigs having babies of two completely dissimilar company cultures. I learned many things, but not much of it was very comfortable. The ground is a fertile medium for the weeds of evil, arrogance, ignorance, and duplicity to grow when watered with the tears of profit. We went through COVID. We went through leadership changes. We had an immense and horrifically timed security event caused by those same people who made the job so painful. I persevered and then left when it got stupid and painful. The reward for success was unemployment. We called it retirement, but let’s be real. Being an expert at odds with stupidity is being an unemployed expert not having to deal with stupidity.
Six years after leaving the intelligence community, I still live on my sailboat, cruising full-time. I’ve sailed along the Eastern Seaboard, ventured into the Bahamas, and explored countless ports and marinas. I don’t miss the big house, the car payments, or the office politics. My life is my own, and I value freedom more than anything. It’s a journey that took me from a life of endless work and consumerism to one of simplicity and genuine happiness. I still want to add to the ability for others to succeed. I want to have had my life impart something lasting and positive, but it’s a lost cause as I look back. Too many burned bridges in my wake. To many people who were partners on a journey, never to look back when our paths diverged.
As I sit on the deck of my sailboat, watching the sunset over the water, I know I made the right choice. It’s not always easy, and sometimes I miss the security of a steady paycheck, but I wouldn’t trade this life for anything. I can make things happen for companies that are willing. I can lead them to a better land if they let me. I remind them I was sitting on a beach when they hired me, and I’ll sit on a beach when they fire me. With that freedom comes the honest assessment they would normally never find. I care about telling people the truth as I see it. That is something more valuable than any consultant they could hire. I also reason to myself. If a company won’t let me help them, I must find someplace that values my opinion. I found a way to escape the relentless grind and embrace an authentic and fulfilling life. I learned that it’s possible to step off the treadmill and create a life that’s truly your own. And for that, I’m grateful.
As I work through the events of life, processing the highs and lows, I have the time to watch the sunset over a glowing globe of bourbon. I worry about money. I worry about my health. I have no social network or programs like my parents did. Those have all been devolved and nothing put in to replace them. Where did things go wrong? Why the struggle against systems that should have been trivial to adjust for low drag and high achievement? I don’t want to be part of a system that destroys the youth of today and grinds them up because nobody cares. The story continues to evolve as I contemplate less in the glass of bourbon and less time to savor it each day.