The Trick My Father Learned Late

Hello Kind and Curious Leader,

Earlier this summer I sat on a video call with Senator Jon Ossoff. The conversation was about the things I care about most, and I came away thinking about none of it. I came away thinking about my father, and about the one thing he did that I have never been able to fully explain. He kept learning, long after most people stop.

My dad was not built to change. He spent his career as a firefighter and an arson investigator in Toledo, Ohio, the city where I grew up. He read scenes for a living, decided what had happened and who was responsible, and moved on. When he retired, he did not slow down. He ran for office and became the mayor of Port St. Lucie, Florida. The job was officially nonpartisan, and he treated it that way, though everyone knew where he stood. He was a lifelong Republican. Reagan, not the version you see today. He was certain in the way men of his generation were trained to be certain, and certainty had served him. It made him good at his work and trusted in his town. It is also the last quality you would expect to bend.

I rarely tell this next part.

For a year, my father and I did not speak. I came out to him, and he could not meet me there. The distance was real and it was painful, and for a long time I carried it as a verdict on whether he loved me.

He did love me. I understand now that his first reaction came from somewhere I could not see at the time. It came from misinformation about what my life would become. It came from a picture of the world he had been handed and never thought to question. Most of all, it came from fear for my welfare, the particular fear of a parent who believes the road just got harder for his child. None of that excused the silence. All of it explained it.

What he did next is the reason I am writing to you. He changed his mind. Not in a weekend. Not because anyone shamed him into it, and not because anyone won the argument, because on the things that matter most no one ever does. He changed because he kept choosing the relationship over the position, again and again, until the position no longer fit.

I knew the day he called and, at the very top of the conversation, before anything else, asked how my partner was. He had never asked before. Not once. It was a small question. It landed like a wedge being pulled out of the ground between us, and a hundred and fifty pounds lifting off my chest in the same second. He did not announce that he had changed. He let me feel it in the ordinary shape of a phone call.

The man who could barely say the word at the start became the man who welcomed the person I loved without a flicker, in rooms full of people his age and his politics who had not moved. That cost him something. Standing. Comfort. The easy approval of peers who assumed he saw the world exactly as they did. He paid it without complaint.

He had a phrase for what he had done. You can teach an old dog new tricks. He said it as a joke about himself, usually with a shrug. It took me years to hear it as anything other than a joke. What he was describing, without the language for it, was a discipline. The willingness to keep revising what you are sure of, especially when revision is expensive and no one is making you do it.

I have spent a career around senior leaders, and I have watched that exact discipline drain out of the most capable people I know. It rarely leaves all at once. It leaves at the moment they succeed. The higher you rise, the fewer people are willing to tell you that you are wrong, and the more your past correctness argues against your present need to learn. Authority is a quiet anesthetic. You stop noticing the questions you have stopped asking. By the time most leaders reach the room they spent their lives trying to enter, they have lost the one capacity that got them there.

So I have started asking myself my father's question, and I will hand it to you in a moment. What am I the old dog about right now. At sixty-one, with a body of work behind me and a reputation I am protective of, where have I quietly decided I am done learning. I do not love every answer I find. There are rooms I still walk into certain I am the most informed person in them, and that certainty is almost never doing the work I think it is. My father learned his hardest trick at an age when the world had stopped expecting anything new of him. I have no excuse to stop earlier than he did.

That is the question I want to leave with you. Not the comfortable version, where you nod along at the idea of growth. The specific one. What have you stopped being willing to learn, who around you can already see it, and what is your certainty costing them.

One last thing, because it is the part that matters most and the part I almost left out.

My father did not become teachable on his own. Something kept the door open long enough for him to walk through it, and it was not the force of a better argument. It was relationship. The steady, unglamorous insistence of the people who loved him that he was still worth staying in the room with. Kindness is not the absence of conviction. It is often the only thing with enough patience to let conviction change. That is the part I have built my life around.

Lead the people who are not there yet as if they can still arrive.

Stay teachable enough to be one of them.

Most of the time, we can.

In Community and Conversation,

Jim