Nobody sends mail to February. January gets the resolutions, December gets the cards, and February gets whatever’s left of your enthusiasm. That’s the problem, and it’s also the opportunity: the one week of the year when you’re least likely to expect good mail is the week a winter letter to your future self is going to land hardest.
I’m writing this in late October, with the first real cold snap of the year happening outside my window in St. Charles and two dogs who both want the one good spot on the couch. It’s the easy version of winter right now. Cozy, a little theatrical. February is the other version. This is a letter for that one.
Why a Winter Letter Matters
Here’s the trick with a tough season: the person living in it is terrible at remembering what the better seasons felt like. In the middle of a gray week, summer seems like something that happened to a different person. You can’t reason your way back to it, because the part of you that would do the reasoning is the part that’s tired.
So you do it ahead of time. You write to February from a day when you still have the perspective, and you hand yourself the thing you’ll need: a reminder of what you like, who you love, what you were looking forward to, and the fact that you knew this stretch was coming and decided to be kind about it.
There’s a long tradition of writing helping people sort through hard feelings. Pennebaker’s expressive-writing research is the best-known example, and I wrote about the honest version of it, caveats included, in the post on letters to your future self and mental health. This isn’t that, exactly. A winter letter isn’t about processing a crisis. It’s closer to leaving a sandwich in the fridge with your name on it.
When to Write It
- Now, while the leaves are still down. The best time to pack a winter survival kit is before you need one. Late October through early December is ideal, and it fits well with the other seasonal letters, like the one for the autumn hinge.
- On a slow Sunday between holidays. The week after Thanksgiving, when the leftovers are gone and the lights haven’t gone up yet, is surprisingly good. Everyone’s a little reflective and nobody has a plan.
- On the first truly gray day. Not the pretty first snow. The flat, colorless one. Write about it while it’s fresh and a little funny.
- Right after New Year’s, if you missed the earlier window. You can still schedule a February delivery in January, since the minimum is one month. Just don’t wait until the end of the month.
What to Put in It
Think of this as a care package in paragraph form. Aim for one page, and keep every item concrete:
- The date and the weather you’re writing in. So February you can compare. “It’s 41 and sunny and I walked the dogs without a hat” is a surprisingly powerful sentence in a cold month.
- Three small things you like about your life right now. Small, not profound. The coffee order, the song in the car, the text thread that makes you laugh.
- A list of things that reliably help. A walk, a phone call, a particular soup, the good blanket. February you doesn’t need to invent a plan. She needs a menu.
- Something to look forward to. A trip, a project, a dinner, the first day it’s warm enough to sit on the porch. Name a date if you have one.
- A little honesty about last winter. What was hard, what got you through, what you’d do differently. You’re the only one with this particular information.
- Permission. To be tired. To cancel plans. To do the minimum and call it fine. People are weirdly more willing to accept this from a letter than from themselves.
- One small task. “Open a window for five minutes.” “Text one friend you owe a text.” Something so small it’s almost rude to refuse.
Prompts to Get You Started
- What do you most reliably forget about yourself in the dark months?
- What does a good day look like for you in winter, down to the specifics?
- Which people make February easier, and have you told them lately?
- What’s one thing you do in the summer that you miss right now?
- What’s the most comforting meal you can make with what’s in the pantry?
- What would you tell a friend who was dreading the next three months?
- What are you hoping to have finished or started by the time the days get longer?
- What’s the most ridiculous thing you’ve done to stay warm?
- What’s a small thing you’re proud of from this year that you haven’t mentioned to anyone?
- What do you want to remember about this exact week?
Pick the three that make you wince a little and answer those. If you’re stuck on the mechanics, my guide to writing a letter to your future self covers the basics, and the New Year letter is a good companion if you also want to write something about January.
Tone: Kind, Not Cheerful
One note from experience as a person who has read plenty of well-meaning advice. Don’t write a pep talk. Nobody in a February slump wants to be told to “embrace the season.” Write like a friend who knows you well and isn’t going to pretend. “I know this is the worst part. Here’s the soup. Here’s the playlist. The light is already coming back, slowly, and you don’t have to be thrilled about it.”
The letters that hold up best are the ones that are a little dry and a lot specific. A joke about the dog shedding on the black sweater does more work than a quote about resilience.
How HoldMyLetter Makes This Easy
The part that makes a winter letter work is that it arrives when you’ve forgotten about it. A note in your phone doesn’t do that; you’ll find it in April while looking for something else.
The Digital Future Letter is $9. You type it at /write, choose a delivery date in the middle of February, and we print it on real paper, seal it, and mail it. If you want the full fountain-pen-and-quiet-evening experience, the Handwritten Future Letter is $19: you write it by hand and mail it in, and we store it and mail it back, sealed, on the date you pick. Delivery can be set anywhere from one month to two years out, and we ship to US addresses only. If you’re deciding on paper, my notes on pens and paper for writing letters are a decent place to start. A smooth pen helps when your hands are cold.
FAQ
When should I schedule a winter letter to arrive?
Pick the week you expect to feel it most. For a lot of people that's the middle of February, when the holidays are long over and spring still feels like a rumor. Hold My Letter delivers anywhere from one month to two years out, so a letter written this week and set for mid-February sits comfortably inside that window.
What if I'm not having a hard winter?
Then it's a different kind of letter, and arguably a better one. You're recording what a good stretch feels like so you can remind yourself of it later. Bad weeks are bad at remembering that good ones happened.
Is this a substitute for support if I'm really struggling?
No. A letter is a small, kind thing you do for yourself, not treatment. If the dark months hit you hard, a doctor or therapist is the right call, and you can still write the letter as well.
Should I write it by hand?
If you have the patience, yes. The Handwritten Future Letter is $19: you write it on paper and mail it in, and we store it and mail it back, sealed, on your chosen date. If you'd rather type it on the couch under a blanket, the Digital Future Letter is $9, and we print, seal, and mail it for you.
How long should a winter letter be?
One page is plenty. You're writing it for a tired person in February, not a scholar. Short and specific will be read twice.
Can I send it to someone else instead?
Yes. A letter timed for the gray part of winter is a lovely thing to send a friend or a sibling who lives somewhere with a worse February than yours. Hold My Letter ships to US addresses only.
Write the letter now, while you can still see the better days from here. February will be glad you did.