Unmasking Leadership: Why Being 'The Boss' Misses the Point

I never dreamed of writing about leadership – heck, I once thought space camp was my true calling (and wore the jumpsuit to prove it). Fast-forward a few decades, and here I am, not as an 'expert,' but as a self-proclaimed student of the art. My own detour into leadership started in the trenches of small business, not out of ambition, but pain and confusion. If you've ever felt lost wearing your 'leader' badge, you’re in good company – and this one’s for you.

Leadership Isn’t a Superpower: Finding Your ‘Why’ When You’d Rather Be Anywhere Else

Most people think of leadership as a superpower—something you’re born with, or a mantle you wear with pride and certainty. But if I’m honest, my own leadership journey started by accident. Pain, not passion, was my teacher. Like Simon Sinek, I never set out to be a leadership expert. In fact, I agree with his words:

"I don't think anybody's an expert on anything... I'm a student of leadership."

That humility is at the core of my leadership philosophy. Leadership isn’t about having all the answers. It’s about being willing to keep learning, especially when you’d rather be anywhere else.

When Success Feels Hollow

There’s a statistic that haunts every small business owner: over 90% of small businesses in the US fail in the first three years. I survived those odds, just like Simon did. But making it to year four didn’t guarantee fulfillment. In fact, I hit a wall. Outwardly, everything looked great. Inside, I felt empty. As Simon put it,

"Superficially everything looked good and yet I didn't want to wake up and go to work anymore."

It’s easy to fake confidence. It’s much harder—and healthier—to be honest about your doubts. I spent so much energy pretending to be happy and in control that I had nothing left for real growth. That’s when I realized: pretending only takes you deeper into the dark.

The Turning Point: Discovering the Power of ‘Why’

My turning point came when I stopped hiding and started searching for my core values. I remember spending three weeks obsessing over the perfect mission statement for my team. I wanted every word to shine. But I was missing the real question: Why does this work matter?

Simon Sinek’s journey mirrored mine. He didn’t find his purpose through triumph, but through struggle. After years of faking passion, he finally admitted to a friend that he’d lost his spark. That honesty was a hard reset for his sense of purpose—and it became the foundation for his now-famous idea: finding your ‘why’.

Leadership Goals: From Accidental to Intentional

Most of us don’t march into leadership with a grand plan. We stumble into it. The real work begins when we stop pretending and start asking deeper questions. Personal leadership isn’t about bravado; it’s about authenticity. When you find your ‘why’, you unlock a well of passion and resilience—not just for yourself, but for everyone around you.

• Leadership Philosophy: Shaped by core values and ongoing self-discovery.
• Personal Leadership: Begins with honesty about your doubts and struggles.
• Core Values: The anchor that keeps you grounded when success feels empty.
• Leadership Goals: Should focus on meaning, not just milestones.

Surviving business failure isn’t just a triumph—it’s a chance to reset your purpose. As I learned (and as Simon Sinek teaches), ‘why’ is the anchor that keeps leaders moving forward, even when they’d rather be anywhere else.

You’re Not The Boss: The Servant Leadership Wake-Up Call

Let’s get honest: being “the boss” is easy. You get the title, maybe a fancy office, and the final say. But real leadership—servant leadership—isn’t about authority. It’s about the responsibility to help others rise. As I often remind myself and my teams, “Leadership is nothing about being in charge; it’s the awesome responsibility to see those around us rise.”

Servant Leadership: Parenting, Not Policing

Servant leadership is a lot like parenting. You don’t pick your team any more than you pick your children, but you show up every day with love, patience, and a commitment to their growth. The best leaders I know approach their role with the same mindset: “The closest analogy I can give to being a great leader is like being a great parent.” You work tirelessly to help your people gain the skills and confidence to excel, not just for the company, but for themselves.

In my first real job, my manager was more than just a supervisor—he was a mentor. He listened, coached, and empowered me to take risks and learn from mistakes. His title meant little compared to the impact he had on my growth. That’s the heart of servant leadership: prioritizing care, trust, and the empowerment of teams over control and ego.

Why “CEO” Misses the Point

Trendy titles like CEO often fail to clarify what leaders should actually do. “Chief Executive Officer” sounds impressive, but what does it really mean? If you can’t read a P&L, you’re not the CFO. If you don’t understand marketing, you’re not the CMO. But “executive officer” is vague. I prefer “Chief Visionary Officer”—someone who shares a vision and inspires others to pursue it. Numbers matter, but a CEO obsessed with short-term wins often sacrifices the long-term health of the organization and its people.

Empowering Teams: The Four Seasons Example

Empowering teams is at the core of a healthy organizational culture. Take the Four Seasons Hotels, for example. Their leadership trusts frontline staff to make decisions—like comping a meal or a drink if something goes wrong. The surprising result? Staff were actually more conservative than management when given this power. Why? Because they felt valued and saw the company as their own. They weren’t reckless; they were responsible stewards of the brand. This is what happens when you foster trust and loyalty through servant leadership.

Leadership is nothing about being in charge; it’s the awesome responsibility to see those around us rise.

Healthy Organizational Culture Starts with People

Too often, leaders claim their top priority is the customer or the bottom line. In reality, your first responsibility is to your people. When employees feel safe, valued, and empowered, they take pride in their work and care for your customers. If they feel threatened or ignored, they’ll focus on self-preservation, not service. Empowering teams means letting go of the urge to control everything and instead building a culture rooted in core values—trust, respect, and shared purpose.

• Servant Leadership fosters trust and loyalty.
• Empowering Teams promotes autonomy and responsibility.
• Healthy Organizational Culture grows when leaders value their people first.

Infinite Games and Honest Messes: Rethinking Success in Leadership

Most of us approach leadership and business with a mindset shaped by competition and clear finish lines. We chase quarterly targets, year-end bonuses, and the elusive title of “number one.” But as Dr. James Carse explained in his theory of finite and infinite games, this approach misses the true nature of leadership. In a finite game, there are known players, fixed rules, and a clear objective—think football or chess. Someone wins, someone loses, and the game ends. But most of what matters in life and leadership—business, healthcare, education, even marriage—are infinite games. The rules shift, new players join, and the goal is not to win, but to keep playing and making an impact.

As Simon Sinek famously put it,

“There is definitely no such thing as winning business.”

“If you want to be number one in your marriage, good luck with that.”

Leadership Philosophy: The Infinite Game

Adopting an infinite mindset is the foundation of Authentic Leadership and a Healthy Organizational Culture. In healthcare and small business, our impact is only as meaningful as our ability to survive, adapt, and grow. Take Parker Seminars, for example: their 73 years of influence only matter because they’ve continued to exist, evolve, and serve. The real leadership goal isn’t a one-time win—it’s sustained, positive impact over time.

Metrics Matter—But They Aren’t the Goal

Metrics and milestones are useful. We need them to track progress and guide our efforts. But when we treat these as the ultimate goal, we risk missing the bigger picture. If you set a target weight or a revenue goal and hit it, that’s great—but the journey doesn’t end there. If you miss it, nothing catastrophic happens, as long as you’re building healthy habits and ethical processes. The trend and the process matter more than the arbitrary finish line.

Ethics, Process, and Intent: The Heart of Transformational Leadership

How we achieve our goals is as important as whether we hit them. Did we act with integrity? Did we nurture our team and culture? Cutting corners or sacrificing values for short-term wins erodes trust, cooperation, and innovation. These are the very foundations of Transformational Leadership and sustainable organizations.

• Human skills—like empathy, communication, and vulnerability—are non-negotiable for a healthy organizational culture.
• Psychological safety enables honest messes, learning, and growth.
• Impact in healthcare or business is only real if the organization survives and thrives.

Ultimately, leadership is not about reaching a finish line. It’s about perpetuating impact, fostering growth, and embracing the honest messes that come with playing the infinite game. The healthiest organizations—and the most authentic leaders—are those who understand that their real legacy is measured not by short-term victories, but by the ongoing value they create.

Messy Truths: Authentic Leadership, Vulnerability, and Finding Your 'Best Friend Test'

Let’s be honest: nobody wakes up as a child dreaming of leading a team meeting or running a business. As I often say,

'I don't think anybody here was doing Chiropractic work on your teddy bears right? This isn't your childhood dream.'

What I’ve learned is that real leadership—the kind that inspires trust and loyalty—doesn’t come from having all the answers. In fact, the best leaders I know are more like great friends than distant bosses. They admit when they’re unsure. They ask for help. They show up as themselves, flaws and all. This kind of Personal Leadership is rooted in vulnerability and honest self-reflection, not in pretending to be perfect.

Vulnerability isn’t just a buzzword; it’s the foundation of Inclusive Leadership. When leaders are open about their uncertainties and willing to share their struggles, it creates psychological safety. Teams feel empowered to speak up, share ideas, and even make mistakes. That’s how innovation and trust grow. I’ve seen firsthand how admitting “I don’t know” can be the most powerful thing a leader says—it opens the door to real connection.

But how do you discover what truly drives you as a leader? How do you find your core values, your “why”? Here’s a surprisingly fun and practical exercise: the Friends Exercise. Sit down with a best friend—the kind of person you’d call at 3 a.m. and know they’d answer. Don’t do this with family; the relationship is too close. Ask them, “Why are we friends?” Watch as they struggle to answer. Our brains don’t easily translate deep feelings like trust and loyalty into words. They’ll likely say things like, “You’re a good person,” or “I trust you.” Push gently: “What is it about me that makes you trust me?” Their answers, and even their awkward silences, will reveal more about your core values and leadership style than any personality test ever could.

I tried this myself, and I learned more from my friend’s pauses and half-finished sentences than from a stack of self-assessments. It’s humbling, sometimes uncomfortable, but deeply illuminating. This quirky exercise is a powerful tool for self-discovery, helping you uncover the authentic qualities that draw people to you—and that can shape your approach to leadership.

In the end, Authentic Leadership isn’t about being “the boss.” It’s about being real, being vulnerable, and being willing to ask the hard questions—of yourself and others. It’s about finding your “why,” even if you never set out to lead. When you lead from that place of honesty and connection, you don’t just build better teams—you build trust, loyalty, and a sense of shared purpose that lasts. That’s the messy, beautiful truth of leadership worth unmasking.