The Letter You Haven't Written Yet

Think about the last time you got a real one.

Not an email. Not a notification. A letter. An actual envelope with your name on it, sitting in the stack of flyers and bills like it had been waiting patiently for you to notice it. You probably stopped. You probably turned it over before you opened it. And when you read it, something happened that doesn't happen with a text. You slowed down. You felt the person in it.

Here's what I want to ask you: do you still have it?

Because I'd bet you do. I'd bet it's in a drawer, or a box, or tucked into something on a shelf. People keep handwritten letters. They don't keep emails. There's something a letter carries that a screen just cannot touch. It costs you something to write one. Time. Attention. The willingness to sit still with someone else in your mind long enough to say what you actually mean. That cost is exactly what makes it matter.

So here's the other question: when was the last time you wrote one?

When the Only Option Was a Stamp

Ryan O'Donnell found himself sitting with that same question a few months ago, though his reason was specific. His friend EJ, someone he'd met playing World of Tanks online and talked with, laughed with, traded movie recommendations with for years, had enlisted in the US Army. Five months of training. No phones. No computers. Total lockdown.

Ryan was a little disappointed. They weren't just gaming partners. EJ was a real friend, the kind whose voice in your ear makes the hard stuff easier. And then EJ had an idea: give me your address, I'll send you a letter.

Ryan said he couldn't believe the thought hadn't even crossed his own mind. He went out and bought envelopes and stamps right away. He was genuinely enthusiastic. There was just one small problem: he hadn't sent a letter in nearly 18 years. The last time was summer camp, when his family sent him letters to keep him company and he'd written back. That was it. Nearly two decades of emails and DMs had replaced the whole thing so quietly he hadn't even noticed.

He wanted to do this right. So he found the Toronto Letter Writers Society, a group of people who gather regularly at a Toronto post office to write letters together and send them to people all over the world, and he sat down with co-founder Andrea Raymond Wong to figure out what "right" even looks like after two decades away from it.

What she told him was this: there isn't really a wrong way. You just think of it like any other conversation. Ask questions. Stay curious about what's happening in their life. Share what's happening in yours. Keep it going. Ryan laughed a little when that landed. He'd forgotten you don't just write about yourself.

Write to the Person, Not the Page

Here's what I would add to that.

Before I write anything, I sit with the person first. I think about who they are, what they mean to me, and then I ask myself what feeling they give me that I'm actually a little afraid to say. Not to make the letter heavy, but to make it specific. Starting there changes everything about what ends up on the page. If I was writing to someone whose consistency I've always relied on, I'd start with that. I'd make sure they knew I noticed, that it mattered. Because how often do we actually say that?

Let it be imperfect. If you make a mistake, scratch it out and keep going. Don't start over. That little mark on the page is part of it. It shows your thoughts happening in real time, and that presence comes through when someone holds the letter in their hands.

Timestamp it honestly, too. "It's late and I had you on my mind." Or: "I've been meaning to write this all week but life kept getting in the way, and I didn't want to let it get away from me." That kind of honesty puts you in the room with them. They're not just reading words. They're reading a moment. And here's how you know when you're done: if you know why you sat down to write, you'll know when the letter is finished. The ending finds you.

Cursive Is Coming Back, and So Is Something Else

Ryan had one more concern, and it was a fair one. His handwriting, by his own description, resembles a doctor writing a prescription while looking the other direction. Andrea's advice was to let that go. Imperfect handwriting is still handwriting, and the effort always comes through.

What's interesting is that Ontario brought cursive back into schools in 2023. The conversations happening on the Nightshift lately suggest people are genuinely rediscovering this, not just as nostalgia but as something that fills a real gap. The Toronto Letter Writers Society has people of all ages showing up now, and Ryan compared it to the vinyl revival: people pick it up as a novelty and then realize why it mattered in the first place. There is something about holding something in your hands that you chose to make.

Gen Z is already adding their own touch, by the way. They've largely stopped capitalizing their writing, not out of laziness but because lowercase feels more conversational, less authoritative and stern. You might get a letter from a twenty-two-year-old that reads like a very thoughtful, very unhurried text message. That's not a bad thing. That's a generation making the form their own.

Here's the part that hasn't left me. We spend a lot of energy worrying about kids who struggle to communicate face to face, to say what they want, to be present with another person. And the answer might have been sitting right in front of us all along: sit down, write it out, practice saying the true thing to a page before you say it to a person. The letter is the rehearsal for everything else.

It starts with us writing them first.

Ryan is waiting for EJ's first envelope to arrive so he knows where to send his reply back. He has the stamps. He has the envelopes. He's ready.

Someone in your life is probably worth one. Find out where to catch the full conversation on the Nightshift and then go write the letter you've been meaning to write.

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