How to Master the Skill of Letter Writing

You don’t have to be a writer to appreciate a thoughtful, handcrafted letter from someone who cares about you. I might be old-fashioned, but I genuinely enjoy taking the time to write letters. From picking out stationery to the excitement of getting something in the mail (besides bills!), letter writing is a forgotten craft that I wish would make a comeback.

How to Master the Skill of Letter Writing.

When you write a letter to a loved one, you are giving them a physical token of your affection that they can keep for years to come.

Here are some tips on how you can become a prolific letter writer and capture your message in a meaningful way.

Choose Your Stationary

One of the reasons I love letter writing so much is because I have a serious passion for stationery. Whenever I buy new paper or notecards they sit on my desk begging to be used.

How to Master the Skill of Letter Writing.
photo credit: Jenny Smith

I like to keep a collection of writing paper, blank note cards, postcards, and parchment paper on hand – but that certainly doesn’t stop me from buying stuff on a whim if the mood strikes.

Some of my favorite places to shop for stationery are Rifle Paper Co, Barnes and Noble, and Etsy.

Having stationery that inspires you will motivate you to write more, in addition to delighting your recipient.

Practice Your Penmanship

Not everyone has naturally good handwriting. The good news is, you don’t need perfect handwriting to compose letters that will be appreciated. But it’s a good idea to at least make sure your writing is legible.

Cursive or Print?

It took me a long time to become confident enough in my cursive to use it in letter writing. And if you don’t feel comfortable writing in cursive yourself, sticking to your natural print handwriting is perfectly fine!

I would suggest scribbling out what you want to say on some scratch paper or a notepad before your draft the letter you’re going to send. Then once you know what you want to write, get out the fancy stationery and use your best penmanship.

As you become more experienced in handwriting letters, try experimenting with some new mediums like calligraphy or typography. There are tons of tutorials online to get you started.

Choose Your Recipient

Whenever I think of sending letters, the first people that pop into my mind are usually elderly relatives. Getting and sending letters was an ideal form of communication for their generation after all. In my grandparent’s basement are boxes and boxes of letters they wrote to each other when they were newly married and living across the country from each other.

While your older relatives will certainly appreciate hearing from you through the mail, don’t limit you letter writing to just your grandparents. For younger generations, getting something in the mail can be a fun, unexpected surprise.

Consider writing letters to:

  • Friends who you don’t live near anymore
  • Nieces or nephews
  • A former teacher or educator you admire
  • Your parents
  • Your kids
  • Someone who was an influence or mentor to you throughout your life
  • Aunts or uncles
  • An employee or subordinate
  • Your local or state legislators
  • Your newspaper editor or another publication you read

Choose a Subject or Theme

I remember as a kid the painful moments my mom would sit us down and make us write letters to our great aunts or other elderly relatives we barely knew. Coming up with what to write was always something I dreaded. Beyond school and what we did on summer vacation, I never knew how to fill the page (writing as big as possible usually).

How to Master the Skill of Letter Writing.
photo credit: Brigitte Tohm

So when you’re drafting a letter to someone, it helps to get a little creative and think about things you can write about besides what’s going on (or not going on) in your life.

Subjects and themes you can write about:

  • An amusing or sentimental memory that you share with that person
  • A story about you they’ve never heard before
  • Recipes you’ve created or your adventures in trying new cuisines
  • Your thoughts or opinions on a current world event
  • A comedic anecdote about something that happened to you recently
  • A review of a concert, movie, or show that you attended
  • A goal you’re working towards and how you attend to achieve it
  • Recommendations for something you think they’d enjoy: books, beers, music, etc.
  • A dream you had that you want advice on interpreting
  • Ask for advice on a current life situation you’re facing
  • Encouragement for a current life situation your recipient is dealing with
  • Create your own listicle on a topic they’ll find enjoyable
  • Describe what your current home, garden, or town looks like using vivid detail for someone who’s never been to your location
  • Fill them in on an interesting topic you recently learned about for the first time

Write for a Special Occasion

To get your creative juices flowing, it can help if you pick a special event or upcoming celebration as a perfect excuse to write a letter. The following are some examples of letters I’ve written and received for special occasions.

Read when letter. For Christmas last year, my spouse and I put together read-when letter kits for our parents. We wrote letters on parchment paper

How to Master the Skill of Letter Writing.
Read when letters.

pertaining to certain days or situations, rolled them up, attached a “read when” tag to each one, then presented them in a glass apothecary jar on Christmas morning. Some of the letters we included:

  • Read when you’re feeling stressed out
  • Read when you can’t sleep
  • Read when you’re sick
  • Read when you need something to make you laugh
  • Read when you’re missing me


In lieu of greeting cards. Instead of shelling out $5 or more for a generic birthday card, consider writing a heartfelt letter instead. This isn’t just for birthdays either. Write letters instead of sending wedding cards (with advice for a happy marriage for the new couple), graduations cards, or anniversary cards.

Holiday letters. Ditch buying seasonal greeting cards in bulk and instead type up a letter of what your household has been up to throughout the year. Add some photos, print off, and send out to all your friends and family.

Annual letters to a close family member.  Every year since I was three years old, my mom has written a yearly letter to me recognizing my growth and accomplishments throughout the year along with her personal thoughts and sentiments. I have almost 30 of these letters now and have saved and cherished them as precious keepsakes of my mother’s love.

Write as a Surprise

Writing a letter to someone doesn’t necessarily require a special occasion. Nothing brightens someone’s day like receiving an unexpected letter from a loved one.

Some good reasons for surprising someone with an unexpected letter:

To offer sympathy. If you know someone that lost a loved one, try to keep them in your thoughts beyond the immediate period of condolences. Often times after things have gotten back to a normal routine, after services are held and end-of-life arrangements have been made, things can start to feel lonely. Make sure these people don’t feel forgotten about by remembering to send them letters of support in the months or even years after they’ve lost their loved one.

To offer encouragement. Maybe you know someone that’s going through a challenging situation, is dealing with a long-term illness, or is simply handling some unexpected life changes. Words of encouragement coming from someone they love, especially when it’s unanticipated, can end up meaning the world to someone.

To offer professional support. Did you hear that a colleague or friend is in the midst of a new job search? Perhaps your nephew who used to do yard work for you is looking for his first after school job. Surprise them with a professional letter of recommendation they can present to prospective employers. Attach a personal note letting them know to feel free to use them as a reference.

Add a Personalized Touch

So you’ve picked out a recipient, written your letter, and are ready to send it off – but you feel like it’s missing something. 

make money as a creative professional.
photo credit: Giulia Bertelli

There’s nothing wrong with sending just a letter and nothing else – it will still be appreciated all on its own. However, if you feel like going above and beyond to impress the person you’re sending it to, consider adding a personalized touch that will take your letter to the next level:

  • Illustrations – if you’re artistically inclined, draw pictures or doodles in the margins of your letters. Or get more elaborate and draw an entire illustration on the back of the page.
  • Clippings – include clippings from magazines or newspapers, like comic strips, recipes, or anything else your recipient would enjoy.
  • Photos – just like handwritten letters, the days of physical photographs are fading into obscurity. Upload your phone’s camera roll to websites like Snapfish to order prints that you can send to family and friends when you write to them.

Choose a Delivery Method

Besides sending off your letter through the postal service, there are other

How to Master the Skill of Letter Writing.
photo credit: Gemma Evans

delivery methods to consider. Most of these will depend on the recipient or the occasion but when it comes to choosing a delivery method make sure it suits the situation accordingly.

  • If you’re writing a letter to a politician or another public figure you could publish it online as an open letter and allow a wider audience to read what you have to say about a particular topic.
  • For recipients that you see on a regular basis and want to be present for when they read your letter, consider hand-delivering the letter to them at an appropriate moment.
  • You can also hide the letter somewhere as a surprise for someone to find later. Hide a letter to your spouse in their briefcase or purse or tuck a letter to a family member in a desk drawer or other hidden location – just make sure not to hide it too well. You’ll want to put it somewhere they’ll actually come across sometime in the near future.
  • As a romantic gesture, or as a pleasant surprise for a friend or family member, send your letter with flowers. Find a local florist that delivers and give them the letter to include with a nice arrangement or bouquet.

When was the last time you wrote a letter and what was the occasion? What’s your favorite letter you’ve ever written or received from someone? Tell me about your feelings on letter writing in the comments section below.

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