The Hardest Leadership Lesson I Had to Learn: Managing My Own Anxiety

Confessions of a Bootstrapped Founder: When the Boss Become the Bully

There is a pervasive myth that toxic leadership always stems from an inflated ego. We tend to picture the "abusive boss" as someone arrogant, power-hungry, and disconnected from their team.

But after years of building my agency, Pennock.co, from the ground up, I’ve learned a much harder truth: sometimes, controlling behavior doesn't come from ego. It comes from fear.

When you are bootstrapping a company, the financial stakes are intensely personal. You don't have VC funding as a cushion. A bad quarter isn't just a slide in a boardroom deck; it's a threat to your ability to make payroll.

I have had to confront the uncomfortable reality that my own worst moments as a leader—times when I was controlling, intense, or overly demanding—were rarely about power. They were about panic. Recognizing this pattern has been crucial not just for my own growth, but for building a culture where my team can thrive despite the inevitable pressures of agency life.

Recently, I was asked to reflect on power dynamics in the workplace. Here is an honest look at where I’ve failed, what triggered it, and the strategies my team taught me for getting back on track.

The Trigger: When Survival Mode Becomes Micromanagement

The first question I was asked was: What factors contribute to someone in authority becoming overly controlling?

For me, the answer is painfully simple: financial pressure.

As a bootstrapped founder, profitability is a constant tightrope walk. There are challenging seasons where the numbers just don’t look good. When that happens, my fight-or-flight response kicks in. I become hyper-fixated on reducing client turnover, because losing a single account feels like an existential threat.

That anxiety creates a vacuum for micromanagement. When I am scared about the company’s survival, my instinct is to grip the wheel tighter—to control every variable, every email, and every deliverable. Unfortunately, that grip often lands directly on my team, manifesting as controlling behavior that stifles the very people I need to help me solve the problem.

The Defense: How My Team Taught Me to De-escalate

The second question is vital for anyone on the receiving end of this dynamic: When an employee feels unfairly targeted by a superior, what are the most effective strategies for asserting boundaries?

I’ve seen this play out in real-time. In instances where my stress escalated into what I now recognize as bullying behavior, the team members who handled it best didn't retreat or match my intensity. Instead, they used what I call the "pause and reframe."

The most effective strategy I’ve seen is when a team member steps back from the immediate fire and re-anchors the conversation to our shared goal. They literally walk me from the 30,000-foot strategic view down to the 3-foot execution level.

By methodically showing me they understand the whole picture—the strategy, the stakes, and the execution plan—they address the root of my anxiety. They prove competence. Once they show me they "get it," my panic subsides, and the need for control neutralizes. It’s an incredibly effective way to manage up.

The Solution: Building a Buffer Through Leadership

Finally, the structural question: What systems successfully deter toxic power dynamics and support healthier relationships?

For Pennock, the solution wasn't a new HR policy. It was hiring senior leaders capable of managing me.

I realized I couldn't be the only pressure valve. Bringing in senior team members who could act as a buffer between my intensity and the rest of the staff was game-changing. These individuals stabilized the team and had the confidence to push back and manage my expectations.

While I am not proud of the moments where I have power-tripped, those high-pressure situations became a crucible for the agency. They forced my staff to regain control of the narrative and learn the difficult skill of "managing up." Ultimately, those messy moments revealed who the true leaders were in my organization.

Leadership isn't about being perfect. It’s about recognizing your triggers and building a system—and a team—strong enough to handle them.