The Leadership Trap: Why Being a "Boss Bitch" Is Holding Back Your Business

Why the "Boss Bitch" leadership style is secretly sabotaging your team's success and how to transform into a true leader who inspires excellence.

The Leadership Trap: Why Being a "Boss Bitch" Is Holding Back Your Team

The Truth About Leading a Team as an Online Business Owner

As a business owner who's built something from scratch, reaching the point where you can hire a team feels like a major milestone. You've followed all the advice: "Hire help to scale," "Delegate to create freedom," "Build a team to maximize impact."

You've done it! You're the CEO with the fancy title. You have people handling your marketing, creating your graphics, running your sales calls. On paper, you're living the dream.

But here's the uncomfortable truth many successful entrepreneurs face: having a team doesn't automatically mean you're leading effectively. In fact, you might be caught in what I call the "Boss Bitch" trap—a leadership style that, despite its popularity, is actually holding back both you and your team.

The Five Levels of the Leadership Journey

Before we dive deeper into the Boss Bitch trap, let's quickly review the leadership journey. Through my experience coaching hundreds of entrepreneurs, I've identified five distinct levels:

The Hobbyist: Treating your business as a hobby rather than an actual business
The Starry-Eyed Hustler: Excited by all possibilities but becoming overwhelmed
The Burned-Out Solopreneur: Making money but unsustainable as you do everything yourself
The Boss Bitch: Having a team but experiencing leadership challenges (today's focus)
The Leader: Creating a team culture built on trust, autonomy, and shared mission

Most entrepreneurs aspire to reach level 4, believing it's the ultimate goal. But there's something deceptive about the Boss Bitch level that we need to unpack.

Why the "Boss Bitch" Level Is Sneaky

If you're operating as the Boss Bitch, you've achieved what many consider success:

You have team members handling tasks
You've successfully delegated responsibilities
You've created systems and processes
Your business generates consistent revenue
You identify as the CEO/founder

Yet despite these tangible markers of success, something feels off. You may find yourself thinking:

"Why can't these people just do their damn job?"
"I could do this better myself."
"I'm wasting time telling people how to do their jobs."
"Having a team is more frustrating than doing it all myself."

Sound familiar? This paradox—having everything you thought you wanted but still feeling frustrated—is the hallmark of the Boss Bitch level.

The Core Problem: Mission Over Leadership

The fundamental issue at this level is that the passion for your mission has overshadowed the value of leadership itself. You're so focused on serving clients and getting tasks off your plate that you've neglected what it truly means to lead.

It's the classic "I love leading but hate managing" predicament. While your team is completing tasks (you wouldn't keep them around if they weren't), you feel like you're pulling teeth to get things done the way you envision.

This creates a destructive cycle:

You feel resentful about managing
This creates tension in your communication
Team members become confused or demotivated
Their performance suffers
This confirms your suspicion that "they just don't get it"
Your resentment deepens

The result? You either remove yourself from the equation (checking out mentally while letting your team operate without guidance) or you remove them (reverting back to solopreneur status). Neither option is sustainable.

The Hidden Truth: Culture Forms Whether You Build It or Not

Here's a critical insight that transforms how you approach team building: a team culture is created whether or not you're building one on purpose.

If you're not intentionally creating a culture of creativity, initiative, shared values, and clear expectations, a default culture emerges—one of confusion and minimal effort. This isn't because people are lazy or incompetent. It's because humans need clear direction and meaningful connection to thrive.

Your team's performance isn't a reflection of their capabilities—it's a reflection of the culture you've created (intentionally or not).

Breaking the Cycle: From Boss Bitch to Leader

If you recognize yourself in this description, don't worry. The fact that you're aware is already a huge step forward. Here's how to break the cycle and transition to true leadership:

1. Start With Trust First

The most counterintuitive but transformative shift is understanding that trust comes first, not after someone proves themselves.

Most entrepreneurs think: "I'll trust them once they show me I can."

Leaders think: "I hired you because I already trust you."

This fundamental shift changes everything. When you start from a place of trust, you communicate differently, delegate differently, and create space for autonomy and growth.

2. Invest in Your Hiring Process

If you want to trust from day one, you need to hire people you can genuinely trust. This means creating a thorough hiring process that identifies not just skills but alignment with your values and mission.

A robust hiring process includes:

Clearly defined roles and expectations
Multiple interview stages to assess different qualities
Practical tests or projects relevant to the position
Values alignment conversations
Clear communication about work style and culture

When you put effort into hiring right, you can relax and trust that you've found someone capable.

3. Understand Team Psychology

Many entrepreneurs don't realize how small adjustments in their leadership approach can dramatically impact team performance. Understanding what motivates people—autonomy, mastery, purpose, recognition—allows you to create an environment where people naturally want to excel.

Simple shifts like:

Acknowledging good work
Providing context for tasks
Offering growth opportunities
Giving appropriate freedom within clear boundaries
Connecting daily work to the larger mission

These can transform your team's engagement and output.

4. Reframe What Leadership Means

The most fulfilled leaders understand that the real joy of business isn't just selling what you've created—it's maximizing the impact of your mission by sharing it with others.

When you view your team as collaborators in a meaningful mission rather than task-completers, leadership becomes not just tolerable but deeply rewarding. You're creating a community united by purpose, which sociologists identify as one of the most fundamental human needs.

My Personal Connection: The Shift That Happens When You're Ready

Like many personal breakthroughs, my understanding of leadership transformed when I hit 30. Suddenly, I found myself ready to confront patterns and beliefs that had been holding me back for years.

The Boss Bitch experience is similar. You may have everything on paper—the team, the systems, the revenue—but until you release outdated beliefs and fears about leadership, you won't experience the freedom and fulfillment you were promised.

Learning From Bad Leadership

We've all experienced poor leadership. One boss I worked for had an excellent hiring process—she consistently hired creative, passionate, motivated people. But as soon as we were hired, something switched. She became controlling, untrusting, and seemingly resentful of having to manage us.

The result? A team that felt undervalued, confused about expectations, and ultimately unmotivated. We had a group text just to complain about her! Not because we were bad employees, but because her leadership style made it impossible to thrive.

The most telling insight: it wasn't that we didn't want to work hard or couldn't perform. It was that her approach to leadership created an environment where excellence couldn't flourish.

The Good News: It's Simpler Than You Think

Transitioning from Boss Bitch to Leader isn't about completely reinventing yourself or your business. It's about making a few crucial shifts:

In how you think about your team: From potential disappointments to trusted collaborators
In how you hire: From filling positions to finding aligned partners
In how you communicate: From directing to empowering
In your daily priorities: From tasks to culture-building

These shifts don't happen overnight, and you'll make mistakes along the way. That's part of the journey. What matters is your willingness to grow beyond the Boss Bitch mentality toward true leadership.

Your Next Steps

If you resonate with this struggle, here are practical steps to move forward:

Take my leadership quiz to clearly identify where you are on the journey (link below)
Examine your hiring process to ensure you're setting yourself up for trusting relationships
Audit your daily communication with your team—is it empowering or controlling?
Schedule dedicated time for leadership development—it's as important as client work
Consider whether your fears about letting go are based in reality or old patterns

Remember, every great leader had to learn these skills. You're not behind or failing—you're evolving.

Final Thoughts: The Unexpected Path to Freedom

The irony of the leadership journey is that the freedom you've been seeking—from overwhelm, from constant work, from being the bottleneck in your business—doesn't come from adding team members. It comes from learning to lead them well.

When you shift from Boss Bitch to Leader, you don't just free your team to do their best work—you free yourself to step fully into your role as visionary and guide.

And that's where the real magic happens.

Ready to break the Boss Bitch cycle? Don't sit in this struggle alone. Take the Leadership Quiz to confirm where you are and get personalized recommendations.

Need personalized support? Book a one-on-one call with me to discuss your specific situation and read past blog posts on the other stages of leadership:

Remember: your exhaustion isn't a sign of failure—it's a signal that you're ready to evolve as a leader.

Want to learn more about the Burned Out Solopreneur stage? Listen to the Permission to Lead podcast Leadership Series.

Categories: : business development, leadership, team building