I’ve been sharing the projects I make most often. The bedtime story. The custom song.
Today: the letter.
This is the one I quietly think might be the most important project in this whole newsletter, because most of us have a letter we’ve been meaning to write for years. To a parent. To an old friend. To a teacher who mattered. To someone we lost touch with. To someone we hurt. To someone we love but never quite told.
The letter has been sitting in most of us for a long time. The gap between meaning to write it and actually writing it is where a lot of the things we most wanted to say have gone to die.
Here’s how to close that gap. About thirty minutes.
You will need:
— One specific person you’ve been meaning to write to
— Your phone
— A ChatGPT account (free)
— A cream envelope and a stamp
— One quiet Sunday afternoon
That’s it. No printer required (though you can print if you want). No design work. No image generation. Just words.
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The most important step is the one you’re going to want to skip.
Step 1 — Talk into your phone (15 minutes).
Open the voice recorder app on your phone. Sit somewhere quiet. Press record.
Now talk to the person you’re writing to, as if they were sitting across from you. Not to a piece of paper. To them.
Tell them what you’ve been meaning to tell them. Ramble. Repeat yourself. Start over. Say the thing you’re scared to say, then say why you were scared to say it. Mention the specific things you remember about them — the phrase they used to say, the time they helped you, the way they laugh, the exact moment you knew you loved them or the exact moment you knew you’d let them down.
Don’t perform. Don’t plan the letter. Talk.
Fifteen minutes is enough. Sometimes you’ll only need five. Sometimes you’ll go twenty.
Step 2 — Get the transcript (2 minutes).
Send the voice recording to yourself. Open ChatGPT on your laptop. Upload the audio file. Ask: please transcribe this recording. Don’t clean it up yet. Just give me the raw words as I said them.
You’ll get back your entire ramble. Read it. Some of it will feel embarrassing. Some of it will feel true. Both are useful.
Step 3 — Turn the ramble into a letter (5 minutes).
Paste the transcript back into ChatGPT. Use this prompt:
The above is a voice memo I recorded to [PERSON’S NAME], who is my [RELATIONSHIP]. I’ve been meaning to write them a letter for a long time and I recorded this to get past the blank page. Please turn this into a warm, natural letter — three or four short paragraphs. Keep my actual phrasing wherever possible. Don’t make it more polished than I am. Don’t add anything I didn’t say. Don’t remove the specific memories I mentioned — those matter. Cut only the repetition, the “um”s, and the false starts. Return just the letter, without a greeting line or sign-off. I’ll write those by hand.
Read what comes back. This is the important part: it should sound like you talking. If a sentence sounds too smooth, too written, too “correct” — cross it out. Ask ChatGPT to try again with “less polished, more like the way I actually talk.”
Iterate two or three times. You’ll know when it sounds right — it’ll sound like you, on your best day, saying the thing you’ve been meaning to say.
Step 4 — Handwrite the greeting and sign-off (5 minutes).
This is the step almost everyone skips and shouldn’t.
Get a piece of cream paper. Copy the letter onto it in your own handwriting. At the top, write Dear [name] in your handwriting. At the bottom, write love, or yours, or I’ve meant to say this for a long time — whatever sign-off feels true. Handwrite those. Don’t type them.
If you can’t write out the whole letter by hand (long letters, bad handwriting, arthritis — real reasons), print the body of the letter and only handwrite the greeting and sign-off. The handwriting matters. It’s the one part of the letter that’s obviously and undeniably you.
Step 5 — Send it (3 minutes).
Address the envelope. Put the letter in. Put a stamp on it. Walk to the mailbox now, before you change your mind.
Do not read it again before you mail it. You will find something you want to change. Every time. Trust the version you have. Send it.
You’re done.
A note on the hardest part. The whole process is about thirty minutes. The hardest part is not the voice memo or the transcription or the editing or the handwriting. The hardest part is walking to the mailbox. The letter, once written but not sent, is heavier than the letter never written. If you put it on your desk for later, later becomes never for most of us.
Set the timer. Talk. Transcribe. Edit. Handwrite. Mail. Do the whole thing in one Sunday afternoon. Don’t split it into stages across a week.
If you do this in the next month, write me. Tell me who you wrote to. You don’t have to tell me what you said. Just tell me you did it, and whether anything came back.
I’m really glad you’re here.
— Tapan
PS — If the person you’re writing to has died, you can still do this. Write the letter. Read it out loud somewhere quiet. Then decide whether to keep it, burn it, or mail it to yourself. Some of the most important letters we write are to people who won’t read them.

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