Being a principal is hands-down the hardest job I’ve ever had. The weight of the expectations and the sheer importance of the role can be crushing. I honestly don’t think I fully grasped how tough it would be until I actually sat in this seat. I’ve always had a deep desire to make people happy, which makes the reality of this position a challenging truth to accept. Leading means knowing you can’t please everyone, but that truth sits with you heavily when you genuinely care about the people you serve. Sometimes, that feeling is simply overwhelming.

It’s funny, because I think caring deeply about people is one of my greatest strengths. I want my staff to enjoy their work, I want students to feel safe on campus, all of that. But my biggest weakness? I care too much about what people think, especially what they think of me. What will they think of this decision? Do they like me? Do my bosses think I’m doing a good job? Am I failing?

So, not only is the weight of being a principal heavy, I’ve piled on this extra pressure to be perfect and to find my worth in what other people think. It’s not working out so well, so I’ve been doing some serious soul-searching about the story I’m telling myself (and others) in this job.

There’s this Eleanor Roosevelt quote I love: “Do what you feel in your heart is right – for you’ll be criticized anyway. You’ll be damned if you do, and damned if you don’t.” It really shifts my perspective. Am I deciding based on what’s right, or just what people want? Honestly, I know I make the right, tough calls (not just what is popular) – it’s just navigating the aftermath that gets to me. I constantly replay situations, second-guessing myself and worrying about who I upset—even though, deep down, I know I made the correct choice.

Now, don’t get me wrong, I’m not perfect. I make mistakes, and sometimes I make the wrong call. But I’m also quick to own up to it. Those are different situations.

So, I keep coming back to that quote. If I’m already doing what I believe is right, how do I stop second-guessing myself out of fear of what people think? I think a big part of it is confidence. Confidence in my own judgment, that I made the right choice, and just letting people think what they’re going to think.

In trying to live this out and find real longevity in leadership, I’m learning that there are a few practical ground rules we have to build into our practice to stop the second-guessing spiral before it starts:

• Interrupt the “Mental Replay” with better questions: When you catch yourself staying up at night replaying a tough interaction, force yourself to change the internal messaging. Instead of spinning on “Did they like how I handled that?” anchor back to your true baseline: “Was this decision honest, selfless, and above all, what is best for our students and our school community?” If you can look at that choice and know it served the kids right, practice drawing a firm boundary and closing the file for the night.
• Expect the friction as part of the job, not a personal failure: Disapproval from others is often just standard administrative friction – it isn’t proof that you made the wrong call or that you’re failing as a leader. Leaders can care about their people’s feelings without letting public opinion rewrite a sound decision.
• Discern between real mistakes and unpopular truths: If you genuinely make the wrong call, own it and pivot quickly. But if the decision was right and simply unpopular, give people the space to think what they are going to think. A leader’s peace of mind cannot be held hostage by the impossible standard of universal approval.

At the end of the day, if we have led with honesty and put our communities first, we have to be able to sleep at night knowing we did the best we could, despite the messy situations.