How I Blew Up My Executive Career
- Chris Howe
- Jan 29
- 13 min read
The Journey to Authenticity: A Love Letter to Corporate America
I have observed that corporate America shapes us in profound ways—through the time we invest, the people we meet, and the sacrifices we make. For better and, at times, for worse, it molds how we see ourselves and what we believe success should look like. It offered me titles, status, rewards, and yes, lots of cash, as I chased the modern-day version of “success.” I pursued that dream with everything I had—climbing the corporate ladder to Vice President first, then building a multi-million-dollar professional services company, and achieving the outward image of success. But in the process, I lost touch with something far more important: my authentic self.
This three-part series, The Journey to Authenticity: A Love Letter to Corporate America, is my reflection on what I gained, what I lost, and the lessons I learned during my experiences working for and with corporations. It’s the story of how I built a life that looked perfect on the outside but was crumbling on the inside. And ultimately, it’s about how I’m finding my way back to who I truly am and expressing that inner truth through my relationships, activities, appearance, and most importantly, how I connect with people.
The first part, How I Blew Up My Executive Career, reveals where it all began to unravel. It’s the story of how I climbed to the top of the corporate ladder—only to realize the cost of losing myself along the way.
How I Blew Up My Executive Career
“I hate the man I used to be, but he'll always be a part of me.Right now, lookin' at my past, I know it's unpretty.Can't hide the pain that I've been through, I wear my scars like my tattoos.The man who I was was wrong, but he's the one who built me.”
~ Jelly Roll, Unpretty
Human evolution has been a complex and multifaceted process, characterized by numerous branches and interconnections rather than a straightforward, linear progression. The fossil record clearly indicates that there is no central line leading steadily from early life forms to modern humans. Instead, evolution has involved continual and intricate branching, with repeated changes in both the rate and direction of development. This complexity underscores that human evolution is not a simple, linear path but a rich tapestry of diverse evolutionary events.
As a species, we began with the primal simplicity of fires, rocks, and caves. Today, we thrive in cities teeming with millions, creating technologies capable of shaping or threatening our very existence. We’ve advanced from walking on two feet—an evolution from fins—to building telescopes that peer into the cosmos. This remarkable ability to adapt, create, and thrive is embedded in our DNA, both as a collective species and as individuals.
Yet, despite this extraordinary progress, I can’t help but feel that on a personal level, many of us are losing something essential: a genuine connection. A connection to our true selves, to those around us, and to the quiet, guiding voice within us—the one that the Quakers often describe as the "still, small voice." It’s a voice that gently urges us toward authenticity, yet is so often drowned out by the noise of our modern lives.
We often wear masks to integrate into society. These masks help us feel accepted but come with a price. Whether consciously or not, many of us fear that if people truly knew us, they’d reject us. We’ve even created labels for this disconnect—“imposter syndrome,” “mommy/daddy issues”—but these terms only scratch the surface of a deeper truth.
In my own life, I’ve seen this pattern play out. When I’m living in alignment with my inner calling, expressing myself with kindness and love, and fostering freedom and unity, I feel connected to my truth. Philosopher and cognitive scientist John Vervaeke refers to this harmony between an individual (the agent) and their environment (the arena) as "agent-arena alignment." He emphasizes that "the identity of the arena is determined by and determines the identity of the agent. And the identity of the agent is determined by and determines the arena."
When this alignment is achieved, it fosters a profound sense of meaning and purpose, enabling individuals to navigate life with authenticity and resilience. Conversely, misalignment can lead to feelings of alienation and absurdity, as one's actions and environment clash, resulting in a disconnection from one's true self and surroundings
Reflecting on my 47 years of life experience, I've come to realize that authenticity is rooted in self-acceptance. Embracing both joyful and painful experiences nourishes the soul, sustaining us through life's challenges. These moments prompt me to continually ask: Who am I? What does it mean to live authentically? By examining the traits and instances that resonate as truly genuine, I find myself pondering: What aspects of our humanity enable us to experience authenticity, reflect it in others, and inspire it within our communities?
What Does It Mean to Be Authentic?
What does it truly mean to be authentic? What does my authentic self even look like?
To be clear, this isn’t about identity in a rigid, fixed sense. In my experience, identity can often feel like a box—restrictive, even limiting. Instead, I’ve come to believe that authenticity is about striving to live a life without self-imposed boundaries—a life that feels limitless in its potential for growth and connection.
Take my high school years, for example. Back then, my identity revolved entirely around being a football player. That jersey was more than just a uniform—it was a badge of belonging. My picture was in the game program, and there was even a sign in my yard that declared my role to the world. I loved that identity.
When I wore that jersey, I felt strong, athletic, and accepted. At the time, I believed those traits defined who I truly was. But looking back now, I can see that those feelings, while genuine in the moment, were largely tied to external validation and comparisons with others. That identity was real to a degree, but it was also fleeting—rooted in a specific role and a narrow slice of my life.
I’m reminded of watching Married with Children as a kid. The main character, Al Bundy, was a middle-aged man who hated his job and felt stuck in life, yet he clung to the glory days of his high school football career. He constantly reminisced about “ruling the gridiron” and kept his old jersey as a relic of his past. The show made it clear: Al Bundy was a joke.
But as I watched, I learned something valuable. That jersey, which once felt so empowering and meaningful, wouldn’t hold the same weight after graduation. It wouldn’t symbolize strength or achievement anymore—it would become nothing more than a reminder of a time long gone. And clinging to it? That would only happen if I failed to find something greater to move toward.
Al Bundy taught me an early lesson: living in the past—or letting an old identity dictate your future—isn’t the way forward. That jersey didn’t make me who I was. It was just a symbol of a specific chapter in my life, not the whole story.
Discovering and embracing your authentic self is a deeply personal journey, unique to each individual. Practices like meditation, journaling, or spending time in nature can help quiet external noise and foster a deeper connection with your inner voice. These moments of stillness allow you to reflect on your experiences, understand your true desires, and align your actions with your core values. By consistently dedicating time to self-reflection and mindfulness, you create the space to hear your inner guidance, leading to a more genuine and fulfilling life.
The Corporate Zombie Trap
As an adult, I fell into a familiar trap. I became what I call a “corporate zombie”—going through the motions, chasing achievements, and convincing myself that my family needed me to work harder, earn more, and provide more. I told myself this relentless grind was for them—that they wanted me to keep pushing so I could give them more. But the truth was simpler: they didn’t need more things. They needed me. They needed me to be present and engaged.
It’s like a Brazilian jiu-jitsu joke: the harder you fight against the choke, the tighter it gets. As professionals with families, we’ve all felt that guilt. We cover up the imbalance with excuses like, “At least I can buy them things and send them places.” Meanwhile, our children and partners watch us—checking emails, taking calls, and being as absent at home as we are during family events.
I recently came across a statistic. I can’t vouch for its accuracy, but it stuck with me: a parent will spend 90% of their total time with their kids by the time those kids turn 18. My son is nine years old—halfway through that timeline—and the thought that my little buddy won’t always be my partner-in-crime around the house is heartbreaking. It’s a sobering reminder of how precious this time really is.
The challenge is clear, though not always easy: make the most of the time we have. For me, that means bonding with my kids, equipping them with the skills to thrive, and—most importantly—teaching them self-acceptance. And the only way I know to teach self-acceptance is to model it myself. It’s about living my truth unapologetically, showing them what it means to be authentic, and being fully present in the moments we share.
The Mill: A Cautionary Tale
The movie The Mill on Hulu captures the corporate illusion with chilling precision. Framed as a psychological thriller about a sinister job interview process, its underlying themes struck a nerve with me. The film explores the dark side of ambition and the manipulative power dynamics that define high-pressure environments. It forces viewers to confront a critical question: At what cost are we chasing success?
The lead character embodies this struggle. They genuinely believe that if they work harder, hit their quotas, and exceed expectations, they’ll eventually “earn” the life they’ve been striving for. But as the story unfolds, it becomes painfully clear that the corporate machine has no finish line. No matter how much effort they pour in, the demands keep piling up. Each milestone is met with yet another, more overwhelming task, eroding their sense of self and leaving them trapped in an endless cycle of exploitation.
For me, The Mill serves as a powerful cautionary tale about the dangers of unchecked ambition. It exposes the illusion we so often buy into—the belief that sacrificing more and climbing higher will lead to fulfillment. But as the movie demonstrates so effectively, this relentless pursuit often leaves people feeling disconnected,
manipulated, and questioning their worth. It’s a stark reminder that reaching the top of the ladder means nothing if the climb comes at the expense of what truly matters.
It’s easy to get swept up in the promises of corporate success. The rewards seem so tangible: bigger paychecks, nicer cars, impressive titles. But what the corporate machine doesn’t tell you is that those rewards are meaningless if they come at the cost of your relationships, your health, and your sense of self. The Mill challenges us to pause and ask: Is the life we’re chasing worth the price we’re paying to get there?
A Wake-Up Call at the Hospital
It all came to a head when my second son was born. Standing in that hospital room, I looked at my wife and thought, We need to figure some things out—and fast. At the time, we already had a three-year-old who was starting to form memories. He’d seen "Drunk Chris" firsthand. To borrow a punchline from comedian Rob Ryan: “Here’s a baby. I’m giving you three years to figure your stuff out… then I’m pressing the record.”
I would have rated myself as a good dad back then, but good wasn’t enough. I wanted to be a great dad. How could I possibly be great for two kids if I wasn’t even great for one? That question hit me like a freight train. It forced me to reflect on my own childhood.
My dad worked hard. During visitation weekends, he always had his laptop out, juggling work and family time. He’d miss video games or cut it close for movies and sporting events because work got in the way. I’m not here to criticize him—he was doing what society told him a successful man should do. And let’s be honest, who doesn’t want to feel safe and successful? That’s all I want for my kids, too. I tell them all the time: My job is to teach you how to be safe and successful.
But watching my dad try to balance work and family taught me what kind of dad I didn’t want to be. I didn’t want to be absent or distracted. I didn’t want to be tethered to my work, leaving my kids to feel like they were competing for my attention—and losing to a laptop.
That day in the hospital, I had an epiphany: To be a good father, I needed to prioritize being a good husband.
Here’s the unvarnished truth—I wasn’t a good husband. I was an adequate father, sure, but I was failing as a partner. At the time, I thought my options were limited: either walk away, find a new relationship, and spare the kids from knowing the difference, or take a brutally honest look inward and confront the hardest question of all—Do I truly love her?
Staying together just for the kids wasn’t an option. A choice like that would have been rooted in fear, not love. I needed to know if love was still there. And then I looked at my wife, who had just given birth to our son. At that moment, I thought, I’ve never seen such beauty in another woman. I love her. I want to be with her.
That decision—to prioritize my marriage, my children, and ultimately myself—marked the start of a reckoning. What followed was even harder: confronting my emotional and mental health, and addressing the alcohol abuse I had used as a crutch for far too long.
Facing the Real Work
I often joke that I’m lucky my vices, triggers, and childhood baggage manifested as outwardly destructive habits—because at least they were impossible to ignore. If left unchecked, my volatile energy would have destroyed everything in its path. My mind is wired for full-spectrum self-destruction. Punching walls (not people)? Sure.
Stepping all over a hard-earned reputation? Absolutely. Burning through money on impulsive, reckless decisions? Every time. That chaotic pattern is one I know far too well.
At the time, a close friend cared enough to pull me aside. They told me they were worried—about my behavior at work, the drinking, and the chatter it was generating. They didn’t want me to destroy the reputation I had spent years building. I brushed them off, dismissing their advice, and it cost us our friendship. Yet, looking back, I’m deeply grateful they said something. That conversation planted a seed. And when I finally started paying attention to how I was spending my time and energy, it was like pouring water on that seed—it began to grow.
After that moment in the hospital with my wife, I knew I had to make a change. So I did something that seemed reckless to everyone around me: I quit my job. With a second child just born, a marriage hanging by a thread, and financial security on the line, I walked away. And, as counterintuitive as it sounds, it was the best decision I could have made.
Over the next nine months, I went to therapy—two therapists, to be exact—working on three critical areas:my marriage, my alcohol abuse, and my lack of emotional regulation. Therapy gave me the space to face the things I had been running from. I also dove into books about emotional management and addiction. Those months were grueling, but they were transformative.
Walking away from my career felt like being handed my life back. I felt 18 again, with the world at my feet, offering endless opportunities for growth and adventure. Those first three years after leaving corporate America were some of the most fulfilling of my life. Quitting alcohol freed up so much time, and I filled it with reading, writing, and creating. I joined the Army National Guard to become a paratrooper. I started training and competing in Brazilian jiu-jitsu. And most importantly, I had the courage to start my own company.
But here’s the twist: over time, I realized I had unknowingly recreated the very thing I had run from. The company I built started to look eerily similar to the corporate environment I had escaped just three years earlier. It was a sobering realization, but one that deepened my understanding of authenticity and alignment.
Looking back, I’ve come to appreciate every twist in the path—whether in my corporate career, as a startup owner, or on the mats in jiu-jitsu. These experiences have taught me that it’s not about labeling moments as successes or failures. It’s about seeing each one for what it truly is: a moment of truth.
Every challenge, every loss, every victory holds its own wisdom if we’re willing to slow down and listen. As Ram Dass beautifully said, this isn’t about acquiring something external. It’s about shedding the layers of ego, expectations, and false narratives we build around ourselves. It’s about reconnecting with what has always been there: our essence, our true nature.
That’s where the real work lies—not in fighting the current of life, but in trusting that still, quiet voice within to guide us back to who we’ve always been.
Living My Truth
Let me be clear: I’m not here to play the role of the “helper.” I’ve fallen into that trap before—chasing validation by trying to save others as if that were my purpose. I’ve learned the hard way that it doesn’t work. Instead, I focus on living my truth—expressing it in ways that feel natural and genuine. If that resonates with others and inspires them to find their own peace, I’m grateful for the connection. But my focus is on staying grounded, building a life rooted in honesty, and finding comfort and clarity no matter what life throws at me.
These days, I keep my message simple, especially for my boys: Do what lights you up. Follow your passions. Just don’t be a jerk to others.
That philosophy isn’t just for them—it’s something I’ve had to apply to myself, too. Looking back, I can see all the times I’ve fallen short of that ideal. I’ve been a jerk to others more times than I’d like to admit. Acknowledging that has been one of the hardest parts of my journey.
The past six years have been about forgiveness—both of others and, most importantly, of myself. There are still amends I need to make, and I will. But alongside that work is an overwhelming sense of gratitude.
Gratitude for the incredible people I’ve met along the way—the mentors, colleagues, and friends who went out of their way to teach, guide, and inspire me. Gratitude for the lessons I’ve learned through pain and progress. And gratitude for the chance to extend that same grace to myself as I continue to move forward, building a life that aligns with who I truly am.
While I have often fallen short of my own standards—facing shame, failure, and the ever-present whispers of imposter syndrome—I’ve learned that the path forward is always the same: to feel the fear, to step forward anyway, and to embrace the lessons that come with failure. I may falter, I may fall, but I am tasked to grow. Above all else, I am human.
Stay Tuned: Let’s Continue the Journey Together
Thank you for reading Part 1 of The Journey to Authenticity: A Love Letter to Corporate America. If my story resonated with you, I invite you to join me as we explore healing, growth, and what it truly means to live a limitless life.
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Upcoming Chapters in This Series:
Part 2: How I Blew Up My Multi-Million Dollar Company – Coming this Wednesday
Part 3: The Path to Expressing My Authentic Self – Releasing Thursday
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I thought the next chapter was coming Wednesday? New chapter to add… “How I blew up my blog post!” Lol