How to Write the Letter You Always Meant to Send

By Frish Brandt, letter midwife

January 18, 2024

Person writing a letter

Image by Unseen Studio

Imagine you are on a plane with severe turbulence. There’s a sudden rattling throughout the plane, beverages start to slide from tray tables, several overhead doors pop open, and small bags tumble into the aisle. The flight attendants are tight jawed and white knuckled as they take their jump seats. The announcement is quick and jarring. Everyone in their seats . . . now!

And you think: Why didn’t I say I’m sorry? Why didn’t I tell him I love him? I should have forgiven her.

Who came to mind when you pictured yourself on the plane? Who came to heart?   

Everyone has a letter in them, a letter they’ve been meaning to write, a letter they would feel lighter having written — to their child, their partner, their long-deceased mother, their younger self, their estranged friend, perhaps even their pet.  

This is an invitation to write that letter. It will only take a few minutes, a few minutes in which you will discover, or uncover, something you might not have known was there.

1. Begin 

Reach for a piece of paper and a pen, or your computer. 

2. Decide who you are writing to 

Child, partner, mother/father, lover/ex-lover, best friend, barista, your future self . . .  

3. List adjectives for this person

Kind, witty, thoughtful, generous, insightful, articulate, guiding, creative, silly, talented, magical . . . These may guide you as you begin your letter.

4. Start writing

Dear . . . 

5. Without second-guessing yourself, continue 

Choose from these prompts or let them inspire your own: Thank you, I’m sorry, I love you, I miss you, I learned from you, When I’m with you, I remember . . . 

Letter writing is not a linear process. You may be surprised where this goes — how you might take a left turn, a right turn, travel a winding road as you find your way to your letter.

In Lee Mingwei’s The Letter Writing Project (1998–present), he invites visitors to sit and write a letter they have always meant to send but never did. Image: Lee Mingwei, The Letter Writing Project, 1998–present. Mixed media interactive installation with three wooden booths, writing paper, and envelopes. Each booth: 114 1/8 × 66 7/8 × 91 in. (290 × 170 × 231 cm). Courtesy of Davis Museum Wellesley College. Photograph by Anita Kan

6. Expand your message

I love the way, I love how you, I love when, What I cherish, I’m grateful for, Without you I never would have . . . 

7. Go deeper still

I wish, It hurt me when, I’m concerned that, I want to understand, The thing that surprised me, What I meant to say was, I wish I had, I wish we hadn’t, If I had it to do over . . . 

8. We’re in the homestretch now

I want you to know, Please remember, I will always treasure, I’m going to miss, Please forgive me, I forgive you, If I could tell you one thing in the years to come . . . 

9. In closing

End however you like: Love, Best, By your side, Ever, With thanks, Humbled . . . Again, trust your intuition. It got you this far.

10. Now what?

Mail it. 

There is something about paper. Something about having a letter in hand to refer to at random times. Your letter is a time capsule of sorts. You change, the recipient changes, but the letter stays the same. It will always have the stamp of the moment you wrote it. 

The magic of this process is that while you might think the letter is for the recipient, you just demonstrated that the letter is first for the writer. 

The proper definition of a man is an animal that writes letters.

― Lewis Carroll

Frish Brandt is a letter midwife, assisting people writing their essential letters. Her practice began serving people in palliative care and hospice, and soon evolved to serve anyone who is mortal. More can be found at

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