You Don't Want An Asshole For A Boss
- jennhyland
- Oct 14
- 3 min read
That’s what my friends said when I was on the fence about applying for a promotion.
For several years, I didn’t really care who was in charge. I came to work, did my job, and stayed busy enough that my supervisors didn’t need to pay much attention to me, not because I was doing anything wrong, but because I was dependable and self-sufficient.
Then one day, my first true asshole boss showed up. And wow, did that change everything.
It was one of the most grueling experiences of my career. I tried to get a transfer but was denied. Up until that point, I didn’t think much about how much a boss could shape a workplace.
But overnight, it became painfully clear: leadership matters.
It’s the boss who sets the tone for the culture. The boss who decides whether employees feel supported or sick to their stomachs the night before work. The boss who can make people believe in themselves or make them dread walking through the door.
That experience became my turning point. It was the moment I decided to apply for my first promotion, not because I was ready, but because I wanted to make sure no one else had to go through what I did.
The Reluctant Leader
If I’m being honest, I didn’t feel ready. I thought I was too junior, too inexperienced, and too uncertain. But here’s the thing: I wasn’t an asshole. And that, I realized, was a good place to start.
When I took on my first leadership role, I didn’t have all the answers but I made a commitment to find them. If someone on my team came to me with a question I couldn’t immediately answer, I said:
“Leave it with me I’ll find out.”
That simple phrase became a foundation for how I led. Over time, I discovered that I had far more knowledge and insight than I’d given myself credit for. And when I didn’t, I had a network of people who did.
I leaned on that network, asked questions, and built trust because leadership isn’t about knowing everything, it’s about caring enough to learn.
Leadership Is a Lifelong Education
Accepting a leadership role doesn’t mean you stop learning. In fact, that’s when the real learning begins.
Throughout my career, I immersed myself in leadership books, articles, and podcasts not just those specific to policing, but from business, education, sports, and the military. I wanted to understand leadership in all its forms, and I found that the best lessons often came from outside my own profession.
Each new team I led came with its own mix of personalities, strengths, and challenges. I had to adapt, shift my communication style, and sometimes completely re-evaluate my approach.
Leadership isn’t one-size-fits-all; it’s an ongoing practice in reading people, building trust, and creating an environment where others can thrive.
The Power of Reflection and Forgiveness
I also learned that leadership isn’t about perfection, it’s about accountability and intention.
There were times when I made mistakes. Times when decisions didn’t land the way I hoped, or when I misunderstood what someone needed. In those moments, I learned the importance of reflection and forgiveness.
Forgiving myself became essential. I had to remind myself that I led with integrity and pure intentions. I never set out to hurt people or make their jobs harder. And that mattered.
Because true leadership comes from a place of wanting to do what’s right, not what’s easy.
Mistakes, when reflected on honestly, are just lessons in disguise. They are what refine our leadership style and strengthen our empathy for others.
Ready or Not
If you’re out there wondering if you’re ready to step into leadership, I’ll tell you what I learned: You’ll probably never feel 100% ready.
But readiness isn’t about having all the answers it’s about being willing to take responsibility, seek information, support others, and keep learning.
The best leaders are rarely the ones chasing titles. They’re the ones who step up because they see something broken and believe they can help fix it. Sometimes, like me, they step up simply to escape bad leadership and promise themselves to do better.
Either way, it’s a start.
So take the leap. Trust that your willingness to learn, adapt, and care will carry you through the hard parts. And remember: leadership isn’t about being perfect, it’s about being present, authentic, and human.
Because the world doesn’t need more bosses.
It needs fewer assholes and more people brave enough to lead with heart.




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