Live. Learn. Lead.

For most of my adult life, I asked my wife what I should wear.

Not because I had no opinions. Rather, I had plenty. But I had learned early that my opinions and her opinions didn’t always produce the same result, and her results were usually better. So I abdicated the decision-making and moved on.

Then I turned 50 and decided I wanted to develop an actual sense of style. Timeless over trendy. Pieces that mix and match. Comfortable enough for a long day, sharp enough for a night out. I started following men’s fashion accounts on Instagram, built a small capsule wardrobe, and felt genuinely good about the direction I was headed.

My wife was not fully on board.

I’ll be honest, her critiques stung a little. I had done the work, made intentional choices, and the person I trusted most to give me honest feedback wasn’t seeing what I was seeing. (If you ever get the chance to meet her, you can ask her about the Great Debate of Cuffed Jeans.) I dug in. I argued my case. I kept wearing what I thought worked and hoped my “confidence” would eventually be contagious. I continued to second-guess myself.

So turned to ChatGPT.

I started photographing my outfits and asking for honest, specific critiques. What works? What doesn’t? What does this combination say about the person wearing it? And what I found was that having a non-judgmental, infinitely patient thinking partner — one with no emotional stake in the outcome — helped me build the skill I was actually trying to develop. Not just a wardrobe. A better eye. A clearer sense of my own judgment and where it needed calibration.

I still spend real mental energy on this. But it’s purposeful energy now rather than anxious, circular energy. The system — imperfect as it is — replaced the chaos.

Here’s what that experience made me think about in the context of leadership:

Most of us are wearing outfits that stopped working a while ago. We built a way of operating, a set of habits, instincts, and default responses, that served us well at one point and now just feels familiar. We’ve stopped asking whether it’s still working. We’ve stopped seeking honest feedback. We’re gutting it out because gutting it out is what has always gotten us through.

The question isn’t whether you need a better system. You do. The question is whether you’re willing to look honestly at what you’re currently wearing — and ask for help seeing what you can’t see yourself.

What’s one habit or pattern in your leadership that you’ve stopped examining because it’s always worked before?