Discover the Inspiration Behind the Oprah-Approved Letters To My… Series

September 1 is Letter Writing Day, so in honor of this “holiday,” we are celebrating the beloved Letters To My… series.

The flyaway success of Lea Redmond’s Letters To My… series has a lot to do with the ingenious design of the fresh format. Each bound book in the series includes prompted letters to an important person in your life: your future self, your new baby, your grandchild, or your romantic partner. Each blank letter smartly folds out for ease of writing, seals up tightly, and then remains attached to the spine to be opened by the lucky recipient at some point in the future.

You might be surprised to learn that the creative path Lea followed to create the original prototype for Letters To My Future Self is steeped in both history and serendipity. We sat down with Lea and her brother (and business partner at Leafcutter Designs) Devin, who revealed how Lea combined a decades-old high school experience with some obscure knowledge about the history of air mail stationery.

The result? The creation of the bestselling Letters To My… series.

Letters to My... Series

Q: So Lea, the original prototype says “Aerograms” on the cover. Are aerograms the original inspiration for Letters To My Future Self?

A: Well, sort of. I’d always been aware of aerograms as a really creative way to save on weight and postage. Why put a letter inside an envelope when the letter itself can magically transform into its own envelope?! And of course, reducing the bulk allowed an airplane to carry twice as much mail. So cool!

My 90-year-old grandfather still tells stories about receiving aerograms, or  “V-Mail” on the front lines during WWII, and how much it meant for morale to hear from home regularly. Also, since aerograms and V-Mail became popular in the 1940s and 50s, they’re sprinkled with wonderful vintage postal graphics.

Vintage Airmail Stickers

I have a little stash of lick-n-stick airmail stickers I’ve collected over the years. They remind me that there was once a time when we couldn’t instantly get in touch with anyone we wanted, anytime, anywhere—and how waiting patiently for a letter (especially a love letter) made the letter itself incredibly significant once it finally arrived. I love that.

Q: Okay, so where did you get the idea to marry this aerogram idea with a letter to your future self?

A: Right. Well, like many other high school students, I had a teacher in 9th grade that asked us to each write and address a letter to ourselves. At the end of senior year, she returned our letters to us. I remember it being really cool to get a letter from my past self, but I’m sorry to say I seem to have lost the letter and now have absolutely no memory of what I wrote! Thankfully, the Letters To My… series of books helps keep memories like these safe and sound.

Anyway, this memory must have been floating around somewhere in the back of my mind while I was brainstorming ideas for new interactive journals a few years ago. At one point, I was playing with the idea of a journal full of empty underground time capsules, which people could then fill with drawings of whatever material things they thought future humans might want to know about. Then suddenly the idea of a time capsule of illustrated objects morphed into the idea of a time capsule of words in the sweet and personal format of a handwritten letter. I kept playing with this idea until it all came together in the tidy, aesthetically pleasing form of a keepsake book of aerograms.

Letters to My... Prototype

As a quick aside, that hand-drawn time capsule idea wasn’t enough for its own book, but it’s one of the seventy-eight fun activities in the newly released Tandem Activity Book.

Q: It strikes me how closely the final product from Chronicle Books resembles your second prototype. Was this a pleasant surprise?

A: Absolutely. Chronicle took my prototype to the factory floor and the production team got it right on the very first try! The blank letters fold down just like I imagined they would, and there’s a page of vintage-inspired stickers in the back to use to seal each letter. To my surprise and delight, they even ran with the string binding from the prototype! I had used string just because I always use a hand-sewn spine in my quick mockups. I think the string looks fantastic and makes the whole package extra special. I also love the fact that this beautiful detail might have been an accident of sorts!

Letters to My... Prototype and Final

Letters to My... Series Binding

Q: Have you always enjoyed writing letters?

A: Yes! I think letter writing is important for two major reasons: the careful reflection it takes to write a good letter and the strength of the connection it makes when your recipient eventually reads it. Taking the time to write with pen on paper instead of email puts us in a better frame of mind to be more reflective. We’ve become very accustomed to firing off lots of emails quickly. While I think it’s possible to compose a very thoughtful email, it just doesn’t happen very often. The process of setting aside the computer (and the phone) and then getting out a beautiful piece of stationery and your favorite pen prompts you to say something better and to more thoughtfully address the reader on the other end. This is exactly what our World’s Smallest Post Service does. It asks people to be their best selves. It’s special. And it’s a special format for saying something important and memorable.

In a way, writing—or receiving—a letter these days is as special as it was hundreds of years ago. If you really want to communicate something from the heart, a letter remains a great way to get someone’s attention and let him or her know that you mean what you say.


Q: What tips do you have for people trying to write their first real letter in quite a few years? Or perhaps their first handwritten letter ever?

A: Include specific details and talk about your emotions. Be sure to pack in the good stuff and make it feel rich. Include your feelings and thoughts about whatever topic you write about. Go deep and include the big “why questions,” as I like to call them. Why did you do a certain thing or make a particular decision? And what does that mean about who you are, or about life generally? Draw conclusions.

Letters to My... Series

If the blank page makes you nervous, make a quick outline before you start. Take five or ten minutes to write a short list about what you want to say. Roughly calculate how much space you have on the page so you can pace yourself along the way. Keep it shorter and tighter than you might—writing is not like talking. Every word counts when you’re writing. When I write a letter, I try to make every sentence feel like a little gem or treasure chest. Think of the words as pearls and then string them together…it doesn’t have to be perfect, just authentically you.

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Give the gift of writing! You can purchase the Letters To My… series here.

Alexandra Brown

Alexandra Brown

Alexandra was the Lifestyle Marketing & Publicity Manager at Chronicle Books. She collects original editions of Hemingway books, owns far too many fleece onesies and aspires to be an accomplished gluten-free baker. She spent a year traveling around the world and documented the experience on her blog:
Alexandra Brown


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