At What Point do you Stop Caring What Other People Think?

It took me a long time (roughly 15 professional years) to truly internalize not caring so much about what my subordinates and colleagues thought about my decisions and my approach to leading. The emotional learning curve is probably different for everyone, but my arc was pretty steep (15 years is a lot of time to be always-cognizant of how people perceived me).

I don't think my heightened awareness of what other people thought of me was necessarily a reflection of some kind of self-centeredness. My personal insecurities really influenced my professional insecurities. I was concerned about my image for a long time because it took me a long while to gain confidence. 

What changed? Perhaps maturity. Perhaps being humbled after raising two daughters. Perhaps I began to lead with confidence once I stopped worrying what other people thought about me. You start making decisions based on what you really believe when you lead with confidence. People believe in your ideas more when they sense you are leading with confidence. They can "feel" a difference about you just by the way you talk and express your ideas. Confident leaders also lead collaboratively because they don't worry about being perceived as a strong or assertive leader. Confident leaders don't have to worry about perception at all because they know they're making decisions with the right ideas in mind.