There is a window in the relationship between a father and his children that closes earlier than most fathers realize. It is the window when the children are still in the house, still oriented toward you as a primary figure, still in the daily rhythm that allows certain kinds of conversations to happen without elaborate scheduling or formality. The window is wider than the early years and narrower than the years that follow. Most fathers occupy it without noticing they are inside it. By the time they recognize it was a window, their children are gone — at college, or in their own apartments, or starting families of their own — and the kinds of conversations that were available are now harder to arrange.

This is one of the quieter regrets of fatherhood, and one of the more avoidable. The conversations that need to have happened by the time your children leave do not need to happen formally. They do not need to be elaborate. They do not even need to be recognized as conversations at the time. What they need is to actually happen — in the car, on the walk, at the end of a long day, in the small windows of attention that exist in any family’s daily life.

What follows is a short list of the conversations that, on the accumulated wisdom of fathers who have done this work and the regrets of fathers who didn’t, are worth having before the window closes. The list is not exhaustive and the order is not strict. The point is to make these things visible, so they have a chance to happen while there is still time.

The conversation about money

Almost every father has things he wants his children to understand about money before they are out in the world having to handle it themselves. Almost no father, in practice, sits down and has the conversation. The conversation gets postponed, partly because money is socially awkward to discuss directly, partly because most fathers absorbed a script in which money was not something you talked about openly, partly because the conversation feels formal in a way that does not fit the ordinary texture of family life.

The result is that most young adults leave home with a money script they have absorbed by inference from their father’s behavior, rather than from any direct instruction. The script may include some useful pieces. It almost always includes some confusions and some patterns the father would not have consciously transmitted if he had thought about it. The young adult goes into the world handling money in ways his father shaped without quite intending to.

The conversation worth having is not, mostly, a lecture about personal finance. It is the more honest sharing of what you have learned about money across your life. What you got wrong early. What you wish someone had told you. What the relationship between money and time turned out to be in your actual experience. What you have come to think money is for, and what it is not for. The mistakes you watched friends make. The trap of always needing more. The role of money in the marriage you have, and what the conversation about it has actually consisted of.

The slow accumulation of long-term thinking is itself one of the more important things to transmit, and it is rarely transmitted by behavior alone. The young person needs to hear what the long view actually looks like from inside an adult life, and what it cost you to learn it.

The conversation about love

This is the one most fathers actively avoid, and the one whose absence does the most damage. Your children are going to be in relationships. They are going to fall in love. They are going to handle some of it well and some of it badly. What they have absorbed from watching you and their mother is part of the template they will work from. What they have absorbed from the broader culture is the other part. Almost nothing else is shaping their preparation, which means there is a lot of unmet need for actual guidance.

The conversation does not need to be embarrassing for either of you. It can be brief. It can happen, often, in the context of something else — a movie you watched together, a relationship of a friend they have mentioned, a moment when something happened in your own marriage that they are old enough to notice. The point is to make some real content available — about what you have learned about love, what is harder than it looks, what is more important than the culture tells them, what the long arc of a relationship actually feels like from inside.

A few things specifically worth saying, in some form, before they leave: that love is built more than found, that the early intoxication is not the test of the long love, that conflict in a relationship is not evidence of the relationship being wrong, that repair is more important than not fighting, that you cannot be fully loved while remaining fully hidden, that the partner who completes you does not exist and the partner you can build a real life with does. The skill of love, rather than the feeling of love, is the part of the curriculum almost no one is teaching, and the part you can offer that the culture cannot.

The conversation about work

Most fathers, asked what they have learned about work across their careers, would have something substantial to say. Most fathers, in practice, never say it to their children in any direct way. The children watch the work from outside — the hours, the moods, the visible pressures — and form their own conclusions about what work is and what it is supposed to do. The conclusions are often partial and sometimes inaccurate.

The conversation worth having is about what work is for, what it is not for, what you have come to think of as worth doing, what you have learned about the trap of overworking, what you wish you had known earlier about how to choose what to do. The specific story of what you have done with your work life — the choices, the regrets, the things that turned out to matter — is more useful to your children than the abstractions. Your particular history gives them something concrete to compare against the choices they are about to make.

Be honest about the parts you got wrong. The boring work you stayed in too long because you were afraid to leave. The promotion you took that was a mistake. The years you worked too hard at the cost of other things you cared about. The reverse, if it applies — the years you under-applied yourself and what that cost. The young adult does not need a sanitized highlight reel. He needs to see what an actual working life looks like from inside, including the mistakes, so he can recognize the patterns when they show up in his own life. What actually makes work meaningful, in the texture of a sustained career, is something he will have to figure out for himself, but he can start from a more accurate map if you give him one.

The conversation about your own father

Many fathers carry, often without quite knowing it, an unspoken story about their relationship with their own father — the things that were difficult, the patterns they did and did not get from him, the work they have done over their adult life to make some kind of peace with that. The children grow up around this without much access to it. They sense, often, that there is more to the relationship between their father and their grandfather than they have been told, but they do not have the information that would let them understand it.

Sharing some of this, age-appropriately, gives your children two things at once. It gives them a more accurate picture of their grandfather, which they otherwise have only at the surface level. And it gives them the experience of a father who is willing to talk about the harder parts of his own family history, which models something they will need when they have to talk about their own family history with their own children eventually.

This conversation can be brief and need not be dramatic. Here’s something I never quite told you about your grandfather. Here’s what I have come to understand about him. Here’s what I have tried to do differently with you. The disclosure produces, often, an unexpected intimacy. The children realize that their father has also been a son, with his own complications, and the realization changes something in how they see him.

The conversation about regret

This is the conversation that almost no one has and that almost everyone, at the end of a life, wishes they had. The conversation in which you say to your children, in some form, what you regret about how you have handled the parenting, the things you wish you had done differently with them specifically, the moments you know you got wrong, the patterns you wish you had interrupted earlier.

The fear that holds this conversation back is the fear of undermining your authority, or of seeming weak, or of producing a response from your children that you cannot manage. The actual experience of fathers who have done this is almost uniformly the opposite. The children, hearing this from their father, are mostly moved by it. They feel met in a way they have not been met before. The acknowledgment of the specific things you have wished you had done differently lands as a kind of repair, even years after the events.

This is the conversation that, done well, can shift the long arc of the relationship into a different and deeper register. The father’s willingness to be honest about his own limitations becomes part of what makes the adult-to-adult relationship possible. The relationship grows up at the moment the father lets himself be seen as a fallible person who has done the best he could and is willing to say what he wishes he had done better.

The conversation does not require listing every shortcoming. It requires naming a few specific ones, the ones that have actually been weighing on you, and offering some acknowledgment. I know I was not good at being present when you were nine. I wish I had been. I’m sorry for that. The specificity matters. The vagueness of I wish I had been a better father does not produce the same effect; the specificity of a named regret does.

The conversation about death

This is the one most fathers avoid most actively, and the one whose absence is felt most by adult children once their fathers are gone. Your children will, at some point, encounter your death. They will encounter it with some level of preparation, or with very little. The level of preparation depends partly on whether you have, while alive, been willing to have any kind of conversation about mortality with them.

This does not need to be a morbid conversation. It can be, in fact, a quite ordinary one — about the way you think about your own mortality, about what you have come to value as you have gotten older, about what you would want them to know, about the practical arrangements they should be aware of when the time comes. The conversation matters as much for its existence as for its content; the fact that you have been willing to discuss this with them at all gives them the experience of a father who is not afraid of the truth of his own finitude, and that experience becomes part of what they carry forward.

The encounter with mortality is one of the more shaping experiences of an adult life, and the children who have had even brief conversations about it with their father tend to handle the eventual reality differently than those who have not. The conversation does not have to predict when it is coming. It only has to acknowledge that the thing exists, in the actual life you are sharing with them.

What this all asks of you

The thread running through all of these conversations is the same. They each require the father to be willing to drop, briefly, the protective social role of fatherhood and to be present as a person with his children. Not all the time. Not in every interaction. But at specific moments, in specific conversations, the role gives way and the person comes through. The children get something they cannot get from anyone else: their father as a complete human being, accessible, available to be known.

These conversations do not need to be scheduled. They are better when they happen spontaneously, in the small openings that ordinary family life provides — the long drive, the late dinner, the walk after a difficult day, the moment when something on television touches a real subject. What makes them happen is the father’s willingness, when the opening appears, to step through it rather than around it.

The window is finite. The children are in your house for a span that will, in retrospect, look brief. The window for these specific conversations is even shorter than the broader window of their childhood, because some of them require the children to be old enough to receive what you have to offer. The years between about twelve and the moment they actually move out are the window when most of these conversations can happen naturally. Once they have left, the relationship continues but the texture changes. The casual conversations of daily life are gone. What remains are scheduled visits and phone calls, and the conversations now require more deliberate arrangement.

You probably know, on some level, which of these conversations are still ahead of you and which have already, in some partial form, happened. The list is yours to take or leave. The work, if you do it, will be one of the more meaningful things you do with your fatherhood. The children will carry forward, into their own adult lives, the version of you they received during these conversations. The version they carry forward is, in significant part, up to you. The window is open. The conversations are available. The choice to have them is, every day for the time remaining, yours to make.