Mistakes I Made in Leadership and What They Taught Me

• Chris The Grad
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• January 10, 2026

By: Chris the Graduate 

Leadership is often portrayed as confidence, decisiveness, and having everything figured out. What people don’t talk about enough is how many mistakes happen behind the scenes. Looking back on my leadership experiences, especially in college, I’ve realized that the moments I learned the most were not my successes, but the mistakes I made along the way.

One of the biggest mistakes I made early on was trying to do everything myself. I thought being a good leader meant being involved in every decision and handling problems personally. In reality, this mindset quickly led to burnout and frustration. I didn’t trust others enough to step up, and by doing so, I limited both my growth and theirs. That mistake taught me that leadership isn’t about control, it’s about trust. Delegating responsibility doesn’t weaken a leader; it strengthens the entire team.

Another mistake I made was avoiding difficult conversations. I worried too much about being liked and didn’t want to create tension within the group. Instead of addressing issues directly, I sometimes let problems linger. Over time, this only made things worse. I learned that leadership requires honesty, even when it’s uncomfortable. Addressing issues early and respectfully prevents resentment and builds stronger communication.

I also underestimated the importance of listening. At times, I focused more on getting my point across than understanding others’ perspectives. I assumed I had the right solution because of my position, rather than taking the time to hear different viewpoints. This taught me that leadership is not about having all the answers; it’s about being open to learning from others. Some of the best ideas come from voices that are often overlooked.

Time management was another challenge. Balancing leadership responsibilities with classes, work, and personal life wasn’t easy, and there were moments when I overcommitted. I learned the hard way that saying “yes” to everything leads to doing nothing well. This mistake taught me the value of setting boundaries and prioritizing what truly matters.

Ultimately, these mistakes reshaped how I view leadership. They showed me that leadership is less about perfection and more about progress. Growth comes from reflection, accountability, and the willingness to improve. Making mistakes doesn’t mean you’re a bad leader; it means you’re learning.

Leadership is a journey, not a title. The mistakes I made helped shape the leader I’m becoming, and they continue to remind me that real leadership starts with humility and a desire to grow.