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How to Write a Letter for Grandchildren You May Not Meet

The instinct is to fill it with advice. Advice is the part that ages worst. Here is what these letters are actually for.

Your Own Story  ·  September 2, 2026  ·  4 min read

People sit down to do this with the best intentions and produce something that reads like a greetings card. It happens because the natural instinct is to write advice and blessing, and both of those are general, and general writing does not survive thirty years.

The letters that land are almost always specific, a little unflattering, and about the writer rather than about the reader.

What to put in

Step 1Who you were at their age

Not what you achieved. What you were like. What you were afraid of at nineteen, what you were bad at, what you thought was going to happen. A grandchild reading this at nineteen is being told, by somebody with authority, that uncertainty at nineteen is normal, and that lands harder than any encouragement could.

Step 2The mistakes, named plainly

Not as cautionary tales with a moral attached. Just what you got wrong, what it cost, and what happened after. Every grandchild reading a letter from a flawless grandparent quietly concludes the letter is not about a real person, and stops taking it seriously.

Step 3What you loved, in detail

The specific things. A place, a piece of music, a Saturday routine, a person. Enthusiasm is the most transmissible thing in a letter like this and it dates far better than wisdom.

Step 4What you want them to know about their family

Where the family came from, who the difficult ones were, what the pattern is. Grandchildren often receive a sanitized version of the family and are quietly confused by it. A straight account from somebody who was there is a real gift.

Step 5One thing addressed to them personally

If you know them, write something only you would notice about them. If they are not born yet, write what you hope to notice. This is the sentence that gets read most often, by some distance.

What to leave out

Letters worth writing separately

Rather than one letter attempting everything, several short ones each doing one job. These four cover most of what people are trying to say when they sit down.

Writing to a grandchild you have not met

The difficulty is that you cannot picture the reader, and writing to nobody produces general prose. The way through is to write to a specific age rather than a specific person. Address it to a nineteen year old. Say so at the top: this is for you when you are nineteen. It gives the letter a register and a subject immediately, and it means you can say things that would be strange to say to a child and are exactly right for somebody at nineteen.

Tell them what you were like at nineteen. That single move does more than any amount of good wishes, because it converts you from a photograph into somebody who was once where they are.

Practical matters people get wrong

Write more than one. A single letter has to serve every possible reader and every possible moment, which is why so many end up generic. Several short letters, each about one thing, work far better than one long attempt at completeness.

Date each one and say how old you are. A letter without a date loses most of its power, because the reader cannot place you.

And do not seal it away somewhere clever. Letters intended to be found after a death are lost with remarkable frequency, in exactly the drawer where they were safest. Put them somewhere ordinary and tell somebody they exist.

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