Battered Executive Syndrome

In early 2023, I faced a professionally driven existential crisis. Not the typical 'Is this worth it?' but the more unsettling question: 'Am I still worthy of this?' Leading a team in a hyper-growth organization as CTO (we had nearly 100% compounded annual growth since COVID) had its inevitable challenges. Missed deadlines, software bugs, and fast-changing demands became my burden—not because they were thrust upon me, but because I believed in extreme ownership as a core leadership principle. This philosophy of taking ultimate responsibility meant that every setback became more than just a problem to solve; it became a weight I carried, a reflection of my perceived inadequacies.

This is the hidden tax of leadership. I've come to think of the weight of perceived failures and relentless expectations as 'Battered Executive Syndrome.' It's not unique to me, but it’s rarely discussed. Many of us, especially those deeply invested in our work, wrestle with self-doubt. It’s as if imposter syndrome is always whispering at the edges of our accomplishments, quietly magnifying every critique or subtle signal into a reflection of our inadequacies. I took every failure far too seriously at the time as if one misstep could rewrite my entire story. Oh, the stories I began to tell myself - “Maybe I’m not a leader that can Get Shit Done. Maybe I’m not as functional as I thought I was as a CTO.” I became a reflection of my failures without learning lessons from them, and being a highly competitive person who is wired to WIN, it began eating at me.

Start Again

So, I began planning my exit. I laid out a succession plan, carefully transitioned my role, and started building something new that felt both intellectually challenging and creatively fulfilling. I wanted to be able to more easily control the ground rules and what "success" looked like. Akin to David Goggins going from Navy Seal to Army Ranger to Wildland Firefighter or Sam Harris resetting his focus in meditation, I embraced the power of starting again. I launched a quantitative finance business focusing on wealth preservation, and have spent thousands of hours creating a systematic trading platform from scratch. In many ways, I was shedding a skin, that shadow that had been following me, not to leave something behind but to uncover something new. Each setback and restart became an opportunity to recommit, refine, and evolve. This perpetual return to the challenge embodied true resilience. Yet I didn't realize that true transformation would come not from escaping my challenges but from embracing an entirely new one.

Leaping into the Unknown

Then, one day, opportunity called. A friend and former colleague reached out with a proposition. "We have a client that needs your help," he said. "They need you." I’ve always said “yes” to new opportunities, even when it means diving headfirst into uncharted waters. My path is littered with examples: moving to Germany to implement software I’d never logged into, taking a job as a mid-level software developer having never written any production code, and taking over a department having never managed someone. It’s a tendency that occasionally gets me into trouble and has led to some of my greatest successes and evolutions. I had to leap into the unknown, knowing the net might not appear. That “yes” turned out to be life-changing.

As I stepped into the fray, the problem was familiar, though the industry wasn't. A near-centenarian business had started down the audacious road of digitizing its operations but was challenged by a new paradigm - proprietary software. Despite their deep experience, they showed remarkable humility in vocalizing their need for help. Here I was, still wrestling with my self-doubt, yet faced with an opportunity that seemed to mirror my journey: a successful organization willing to acknowledge its vulnerabilities and start fresh. My insecure monkey brain battled the urge to take on this challenge, but something about their openness to change resonated deeply with my experience.

I discovered something transformative about leadership, growth, and two big lessons through this unexpected turn.

Lesson 1: On Humility…

One of the most important revelations for me was that I had to do something I hadn't done in nearly a decade: earn trust from the ground up. Before this, I'd spent years with the same executive team, each relationship built on battles fought together. I didn't have much to prove to stay there, and that was likely what made the trounces of failure slap me in the face even more. I would say to myself, "How could this be? Look at what I've built!"

Now, I was back at the starting line, with new doubts but a different team. I had to remember, redefine, and reimagine what made me trustworthy. The path forward demanded a new operating system built on the delicate balance between hubris and humility. It meant having the confidence to say, "I am good at this, and it is my craft," while embracing the humility to admit, "I don't know anything and am just making it up as I go." This wasn't about choosing between expertise and uncertainty but finding strength in their coexistence. To say, 'I am good at this,' and then in the same breath admit, 'I'm also figuring this out as I go,' became the essential dichotomy of authentic leadership.

Lesson 2: Winning Together

I also found myself on the ultimate team. They weren't operating internally with an “us-versus-them” mentality but instead with a unified front driven by a desire to win. What I experienced went more profound than just doing a good job daily. This was a team that showed true partnership—a team all striving for the same outcome. Sure, there was sometimes frustration, but that's almost a given when the goals are big and ambitious, and the people are winners. What struck me was that this team was operating as a team, where every position felt wanted and needed. Winning wasn't about individual survival; it was a shared mission, a victory we could all claim.

Only in hindsight can I reconcile how my previous environment had strayed from this path. A subtle culture of "shifting pressure from team to team" had emerged, keeping the flywheel spinning but ultimately leading to finger-pointing and hunting internal ghosts whenever progress stalled. While our previous success might have been impressive—near 100% growth year over year—looking back, I can't help but think those wins were more a product of market momentum than true cohesion. We were so busy finding the pariah that we forgot the fundamental truth: true success isn't about passing the load; it's about lifting it together.

Fail to WIN

Self-doubt is far more common among leaders than most admit. That "Battered Executive Syndrome" I experienced—the weight of perceived failures and relentless expectations—is a universal step in everyone’s leadership journey. Like learning to walk, leadership is a series of stumbles and falls, where the weight of our perceived failures often comes from taking ourselves—and these inevitable stumbles—too seriously. As seriousness takes hold, the stories we tell ourselves stray from the Truth, becoming shadows of insecurity that let demons take hold.

In a recent interview with Lance Armstrong, Kimbal Musk shared advice from his brother to "fail fast and use that feedback to grow iteratively." This principle mirrors the fundamental nature of growth: just as a child learns to walk through countless falls, each providing vital feedback about balance and momentum, leaders grow through cycles of failure and adaptation. What feels like proof of inadequacy at the moment reveals itself over time as a necessary step toward mastery—each stumble teaching us to balance hubris with humility and individual achievement with team success.

Leadership isn't about achieving perfect balance on the first try—it's about embracing the wobbles and falls along the way. The path forward requires the humility to accept help when stumbling and the wisdom to lift others when they fall. Growth happens when you let go of the need for perfection, finding strength in the vulnerability of learning alongside your team. Not taking yourself—or your failures—too seriously becomes the key to staying in the game.

Finding one's vocation requires this continuous cycle of falling and rising, each experience demanding that delicate balance between confidence and humility, individual drive and team cohesion. It requires finding people who understand that winning means everyone crosses the finish line together. The key lies not in avoiding falls but in how you handle them: own them, inspect them, and accept them as part of the process. Only then can you transform these stumbles from perceived failures into the steps that move you and your team forward.