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  The art of storytelling

My friend Pip once told me about the regular letters her grandmother used to write to her while Pip was living on the other side of the world, in London. They were little snippets of home, missives from Grandma's rose garden in Victoria. Those letters meant the world to Pip. They brought joy through loneliness, and helped to stave off homesickness.

Many years later, Pip and a group of other friends gathered at my dining table with food and wine and pretty stationery on hand, to write letters to our loved ones. Pip picked up a pen to write to her Grandma, then paused over the blank paper. As has happened to so many of us, and despite all that was going on in her life, the words wouldn't come. She didn't know what to write, or how to start.

Sometimes it’s hard to know how to start a letter. Small-talk feels awkward, not to mention redundant, on paper. "How are you?" and "What's new?" carry even less meaning when the time between question and answer can stretch for weeks, months or even years.

Often I find the best way to start my letters, whether I am writing to a complete stranger or a beloved grandmother, is simply to tell a story. Launch straight in! Tell them about something you saw on the walk to work or school, about a new hobby you’re learning, something funny that happened to you last week, a new TV show you’ve been watching. Describe a storm. Recall a special memory from your childhood, or recount one from just last week.

In my e-book "Making Mail," I used the example of a letter (or to be precise an email letter) that Meg Ryan's character Kathleen Kelly wrote to Tom Hanks' character Joe Fox, to illustrate how beautifully storytelling can work in a letter.

"Once I read a book about a butterfly on a subway and today, I saw one. It got on at 42nd, and got off at 59th, where I assumed it was going to Bloomingdales to buy a hat that will turn out to be a mistake as almost all hats are."

Really when I'm talking about telling stories here, I'm talking about anecdotes. Anecdotes are just simple, short stories. Or fragments of stories that are complete in their own right. No twists and turns, just the one plot. But it needs to be a plot that has special meaning to you.

Unless you're in the mood for it, you don't need to write a long, involved story in your letter. Sometimes, short really is sweet. Think about the butterfly-on-the-subway story above. Or this heartbreaking and entirely complete story (purportedly by Ernest Hemingway although that is not proven) written in just six words:

For sale: baby shoes, never worn.

And another thing: your anecdote does not need to be grand or clever, it only needs to be personal. Share emotions and experiences, not events. If you go to see a show, don't write a review of the show, write about your experience of it - of how you got there, of your seats, the company you were in, the food you ate afterwards. Of the show itself, write how it made you feel, thoughts it prompted, memories it triggered, conversations it inspired. You get the picture!

Here's an anecdote I once shared in a letter to Pip Lincolne (a different Pip to the one above), for her "52 Hellos" project:


In this lesson, I'm going to teach you the nuts and bolts of writing a great anecdote. It's like a recipe for writing a story, with all the ingredients listed and a method that tells you what to do with those ingredients, in what order. But if you feel that your words still aren't coming together the way you want them to, that your anecdotes are not as interesting or compelling or touching as you want them to be, I want to remind you of two things:

1. You are writing a letter, not a Booker Prize winning novel. There is a LOT of leeway you can take with a letter, because people are so forgiving of you. They are almost always so deeply touched and happy that you have taken the time to write to them and share your thoughts and experiences with them that they will forgive just about anything in your writing. Go ahead and give it a try, and you'll see what I mean.

2. Even with this forgiveness in the bag, you still want to write well. I get it! Plus, mastering 'the art of telling an anecdote' will certainly help you in all kinds of other situations, even in business (well-told anecdotes are great ways to introduce and illustrate reports and presentations).

If you use the guidelines in this section, and the writing tips that follow, your writing will definitely improve. It just takes practise, and letters are the perfect place to practise because of point 1 above (you're making someone's day anyway, and they will forgive just about anything).

Don't give up: take heart from the following words of encouragement by the master of storytelling, Ira Glass. Practise, practise, practise.


Setting the scene might be as simple and short as just one sentence, or even half a sentence. You just need to establish where in time and place the action is taking place.

  • "Yesterday at work..."
  • "When I was only five..."
  • "At the beach on holidays..."
  • "In my imagination..."

But your anecdote will be more compelling or emotive if you put yourself in the scene. What was this scene to you? Use sensory details in that scene. Things you saw, smelled, tasted, touched...


You're not writing a novel, so you don't need to spend pages and pages on the set-up. Once you've set the scene, get straight to the point: dive straight into the action.

This is not rocket science. Say what happened, in the order in which it happened. If you're struggling to keep things moving along in a lively or interesting fashion, use joining words to build excitement and help take your story to its conclusion. For example:

  • First of all
  • After that
  • Then
  • Can you imagine my surprise
  • Meanwhile
  • Later
  • By the time I realised it
  • To top things off
  • Anyway
  • Finally


As you share what happened, aim to answer all five W-questions, in any order you please. Even if you think some of these questions are not relevant to your story, answer them in your head. Sometimes, you'll realise that answering these questions in the telling of your story adds colour to your anecdote, or helps to move the action, interest or emotion forward. These are your W-questions:

  • WHAT happened?
  • WHO was involved?
  • WHERE did the action take place?
  • WHEN did it happen?
  • WHY did things unfold this way?


Don't forget that the emotional core of your anecdote is you. As I said earlier, don't describe an event, describe how the event made you feel. If you find you're getting lost in facts and events, just keep returning to your emotions. How did you feel? What were your motivations? How do you feel about it all now?


What I mean is, don't leave your reader hanging. If you have raised questions in your anecdote, try to answer them. Maybe there's a lesson learned, or a moral to the story. Or maybe not! If you don't have a neatly tied up answer, at least present them with a conclusion of some kind. "I never did learn what that meant, but it helped me see the world in a glass-half-full kind of way." You're making a final comment on the story, or, concluding by explaining how things are now that the action is over.

The butterfly on the subway and its imaginary trip to Bloomingdales was the action of that story. The likelihood that the butterfly's choice of hat was a mistake was the conclusion.

Use the worksheet below to practise the skills of writing an anecdote.



If you're wondering what to write about, or think you don't have a story to tell, I'm here to help! After all, a good anecdote is simply an everyday event or recollection, made into a "memorable moment" through the magic of your writing. And we all have events and memories.

The following printable list contains 101 writing prompts that you can turn into anecdotes for your letter. Most ideas on this list will adapt equally well whether you are writing to a close friend or relative, or to a new pen-pal for the very first time.

Beautiful Letter - 101 writing prompts (links).pdf