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Three Questions and A Suggestion: Letter Writing 101

My love of letter-writing was an inheritance, passed down from my Grandmother Neenie.

When I was a kid, she would send a letter to me and my sister every week. She taught me something special—to make letters about the receiver. Even though my sister and I lived in the same house, my grandmother still took the time to send us separate cards. This showed we each had a distinct relationship with her—we were each unique to her. She always made her cards about the person she was sending it to, and didn’t take shortcuts. She could have put the two cards in one envelope—but she didn’t even do that. She took the care to put them in separate envelopes.

When you sit down to write a letter, a hundred questions might flood through your mind. “What should I say? Is my handwriting ok? Am I doing this right?” But these aren’t quite the right questions to be asking. Instead of focusing on yourself, to write truly meaningful letters, think about the other person.


When you write a letter, you want to think about the person you’re writing to. I know this sounds obvious, but it can be easy to end up just sharing whatever is going on in your life. It is important to share your own experience, but you want to do it in a way that will impact your reader.


Letter writing doesn’t have to be complicated. Here’s three questions to help you write a personalized letter, and a suggestion on how to make your letters special and interesting.


Three Questions to Ask When Writing a Letter

1: How Is Your Reader Feeling?

One of the most important questions to consider when you sit down to right is how they might already be feeling. How are they doing in general? Of course, you won’t know exactly how they’ll be feeling on the day they receive the letter, but you can know the general theme of their life lately. Right now, we’re in the midst of the COVID-19 pandemic, so everyone is going through the challenges of being apart from friends and family, which affects the way you write a letter right now. Our current situation shapes how your letter-receiver is feeling.

But there’s other, more ordinary things, that can influence how they feel. Have they recently had a baby? Their life is likely full of a lot of excitement, and little sleep, and your letter should speak to that. Has there been a loss in their family? Your letter then will be completely different. How is their job going? How is their health? How is their life in general? You want to consider the state they are already in.


2: How Do I Want to Make Them Feel?

Next, you want to consider how you want the person to feel through this letter. How do you want them to feel when they receive it in the mail? How do you want them to feel when they open the letter? How do you want them to feel reading the letter? Is it meant to be enjoyable? Is it humorous? Hopefully your letter is enjoyable, but there’s likely different kinds of emotions you want the reader to experience.


One way to help your reader feel special is by paying attention to what you include with your letter. Make it something the person is going to delight in receiving.

My Neeni always included a dollar bill and a piece of bubble gum in every card she sent me. For a very young kid, that was a special thing to receive in the mail. I didn’t have any money of my own, and my mom didn’t buy us bubble gum. It wasn’t hard for my grandmother to include that—but it made the letter very special to me.


So when you’re writing your letter, think of ways to make it special for them. This can affect the design choices you make, the type of paper, ink, wax seals, or stamps—but it can also include extra things you add to make the letter fun.


My friends Mia and Faith are wonderful at doing this with their letters. Mia is an amazing calligrapher, and fills the margins of her letters with tiny watercolor painting and inspiring quotes. Her letters feel so precious, and often I don’t want to recycle even the envelope, because my name and address are so beautifully written. Faith uses special elements to make her letters unique. From using vellum to wrap the letter, or putting on a beautiful washi tape that she had mentioned to me before, every detail is thought out. Her letters are gorgeous—and every detail is specific to me. Both of my friends think about how they want me to feel when I receive the letter, and take the time to make the letter extra special.

Little actions like this may be very simple (such as the bubble gum), but they show special care. These details say, “I remember and I see you and I care.” So before the reader even gets to the words of the letter, those little details speak to them.


3: How Do I Want Them to Feel When They Finish?

Finally, think about how you want them to feel at the end of the letter. What type of feeling do I want to leave them with?


Do you want them to feel excited about an upcoming visit? Do you want them to have that happy contentedness that comes after a long chat over coffee with a friend? Do you want them to see the gravity of a situation? Do you want to make them laugh? As you ask this question, it will be easier to think of what to say, for you know the goal that you are pointing toward.


If you ask these questions before you write, you’ll avoid 95% of the things people say in letters that just shouldn’t be said, because you’re tuning into how the reader might be doing, and writing your correspondence based on that. Later, we’ll look at specific types of correspondence: thank you notes, condolence notes, love notes, and the different nuances in each—but if you start with “how are they feeling?” and “How do I want to make them feel?” and make the letter about them, it’s going to be much more effective.


How to Make Your Letters Special

As I grew, I continued to write Nini and other family members, but when I went away to school, my letter-writing took a different turn.


When I was away at school, I wrote letters to friends who were back home. And when I was back home over the summer or winter holiday, I wrote friends from boarding school who were back in their respective home towns. In those letters, I learned more about letter writing, and how to make it interesting, particularly for the age we live in, when a lot of our updates are already online. Granted, we weren’t using social media when I was in boarding school, but we did have email, so if something was urgent, it was very easy to get that update to a friend regardless of where they were located in the world.


I learned that in modern letter writing, you want to keep it interesting, and tell people something they don’t know. These can be very everyday things: interesting things you’ve been during the day, or interesting conversations you’ve had. Did you get a new book from the library you’re excited to start? Share about it. Are you in the middle of a big project at work? Tell them about the breakthrough you just made. Did you finally get the first snow of the season? Describe to them how it covered the shrubs, and blanketed the hard edges of that old wall.


You can also share something more profound. Maybe you’ve been thinking about philosophy, or pondering on something in your life. Those are both interesting things, but things we don’t often share about on social media. That makes them the perfect thing to share about in letters—and helps your reader to feel like you’re sharing something intimate and personal with them.


Even if you went on a trip, instead of telling them all about the things they saw pictures of, you might tell them something unique on the trip that made you think of them. Tell them about that spicy dish, and how it made you think of how they loved to eat those spicy peppers. Again, you’re sharing something interesting from your own life, but still bringing it back to them.


You can also include some of those special elements we talked about to make your letters more interesting. Obviously, I love wax seals, as they’re an integral part of what I do with Kathryn Hastings and Co. I love to talk about the symbolism of each seal, how you’re sealing an intention on each letter. For me, it often feels incomplete if I haven’t set an intention on the outside of a letter through the symbolism of a seal. But you don’t need to purchase a seal to do that. If there’s something that you want to add that is a special detail, you could draw it, or get a sticker, or include some washi tape. Anything that you feel would be special for them, would be something you would want to consider to make that letter unique.


Letters are a beautiful way to communicate. It’s a way to physically reach out through time and space, and say, “I care.” You don’t need to overthink your letter-writing—just remember those three questions, make the letter about your reader, and find little ways to make it interesting. Above all, just start writing! Letter writing is an art—and any art take practice. As you write, you’ll become better and better—and build better relationships as you do!

I hope these tips have been helpful. If you have other questions or ideas that you want me to cover, please comment them below!


Your most humble and faithful servant,

Kay Collier





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