Parenting advice books have their uses: sleep schedules, developmental milestones, when to call the pediatrician. What they can't do is prepare you for what parenthood actually feels like from the inside — the weight of it, the way it changes your relationship to your own mortality, the things you find yourself passing on without meaning to. For that, you need literature. Not books about parenting, but books that understand what it means to be responsible for another person's life, and what families do to each other across time.
The most beautiful book about a parent writing to a child is Gilead by Marilynne Robinson. An aging Iowa minister, knowing he won't live to see his young son grow up, writes him letters. The letters are a meditation on faith, on what a life spent in one place means, on what he wants to give the boy that can't be given in person. Robinson's prose is slow and exact and full of light — it describes parenthood as a form of prayer, which is either the most or least secular thing you've heard depending on where you start. What it gets right is the asymmetry of parenthood: the parent knows things the child can't yet understand, and writes anyway, hoping the words will mean something later.
For the conversation between parent and child about what the world actually is, there is nothing better than Between the World and Me by Ta-Nehisi Coates. Written as a letter to his teenage son after the acquittal of a police officer who killed a friend, it is honest about what Black parenthood in America requires — telling your child the truth about a country that will see his body before it sees him, without destroying his sense of possibility. Coates doesn't offer false comfort, and that honesty is what makes it necessary. Every parent struggles with how much truth to give a child about the world. Coates is a guide to doing it without lying.
Family as something inherited — a set of patterns and griefs and ways of leaving that get passed along without anyone deciding to — is the subject of Housekeeping by Marilynne Robinson. Two sisters in rural Idaho are raised by a series of female relatives, each of whom disappears in different ways. Robinson is interested in what families transmit that isn't spoken — the styles of attachment and detachment, the ways of being in the world that children absorb from the adults around them. The novel is strange and luminous and uncomfortable in the best way, and if you have ever found yourself parenting in ways you don't quite recognize, it will feel familiar.
The most ambitious account of father-son dynamics in all of Western literature is The Brothers Karamazov by Fyodor Dostoevsky. Fyodor Karamazov is a terrible father — selfish, cruel, absent in the ways that matter — and his sons embody different responses to that inheritance: pious, intellectual, sensualist. The parricide at the center of the novel is a literal event and a psychological one simultaneously. Dostoevsky understood that what fathers do to sons reverberates across generations, and that the options available to children in terrible families are all imperfect. It's the darkest book on this list and also the most generous in what it understands about human limitation.
The experience of losing a parent, and what that loss does to a person's understanding of their own family, is the subject of The Year of Magical Thinking by Joan Didion. After the sudden death of her husband of forty years, Didion investigates her own grief with the same precision she brought to everything she wrote. What emerges is a portrait of a marriage, of a shared life, and of what it means to have raised a child with another person and then to continue alone. It's not a parenting book by any conventional description, but it is one of the most precise accounts of what the long relationship between two people who raise a child together actually looks like — from the outside of it, when one of them is gone.
Finally, The Warmth of Other Suns by Isabel Wilkerson follows three individuals through the decades of the Great Migration — six million Black Americans who left the South between 1915 and 1970. In each story, the decision to leave is also a decision about what to give to children not yet born, what future to try to make possible. Wilkerson writes about parenthood as one of the primary motors of history: the willingness to leave everything you know because you want something better for the people who come after you. It's history as biography, and it's the best account I know of what people actually sacrifice when they sacrifice for family.
These books won't help you with sleep training. They will help you understand what you are doing and why it matters, which turns out to be the harder question.