The Art of the Personal Letter: A Guide to Connecting Through the Written Word

The Art of the Personal Letter: A Guide to Connecting Through the Written Word

by Margaret Shepherd, Sharon Hogan


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When was the last time you wrote a letter? Or received one in the mail?

These days, it’s so easy to dash off a quick e-mail or text message or make a cell- phone call while you’re on the run that you may rarely make time for letter writing. But letters are a time-honored form of connection that simply cannot be equaled or replaced by faster methods of communication.

The Art of the Personal Letter
reclaims this lost art, giving you the gift of leisurely expression and allowing you to write beautiful, enduring letters to the people you care about—be it by hand or on a computer. For any occasion—whether you’re reaching out to connect with a long-lost friend or you want to express condolences with grace—author Margaret Shepherd gives you both the inspiration and the tools to write a memorable and meaningful letter that will be cherished by its recipient for years.

Filled with marvelous examples of common types of letters, The Art of the Personal Letter provides helpful guidelines to enhance your unique voice and inspire you to start that holiday letter or difficult letter of apology. From choosing just the right words, the right stationery, and even the right pen or font, you’ll learn everything you need to know about the timeless art of the personal letter.

Product Details

ISBN-13: 9780767928274
Publisher: Crown Publishing Group
Publication date: 09/16/2008
Pages: 240
Sales rank: 616,091
Product dimensions: 5.26(w) x 7.41(h) x 0.99(d)

About the Author

Margaret Shepherd is a noted calligrapher and author whose clients include numerous headliners. The author of thousands of personal letters and fourteen hand-lettered instructional books on calligraphy, including the bestselling Learning Calligraphy, she has exhibited her work in many museums and galleries. She lives in Boston.

Sharon Cloud Hogan has written and edited several books for general readers . She leads workshops on nonfiction writing for physicians, and she is a manuscript editor at The New England Journal of Medicine.  She lives near Boston.

Read an Excerpt


The Art of Connecting

What a lot we lost when we stopped writing letters!

You can't reread a phone call.

—Liz Carpenter
You're so connected. You check your messages from a gizmo in your pocket, a laptop on your kitchen table, and a desktop in your office. You read e-mail from work while you are at home and personal e-mail on the job. You send out jokes, photos, breaking news, invitations, and announcements. You phone people between classes, on the train, and before a concert. (When you phone from the bus, you always seem to sit next to me!) You leave lots of messages, often timing your calls to avoid actually talking to anybody in person. You buzz your friends' cell phones with telegraphic short text messages, converse in real-time cyberspace with instant messages, and add a sticky note to any piece of paper you send around.

Although you've traded quality for quantity, you've still got all your connections covered. You don't even buy a quart of milk without a quick text message home to see who wants fat-free and who wants 1 percent. Your family and friends know that you're thinking of them, even when those thoughts only come out as "How r u?" on their cell-phone screens. You may not feel sure that you've used exactly the right format for every message, but overall, you're so connected, you couldn't be missing anything. Or could you?

In spite of all of your efforts, you may still be missing the most satisfying, expansive, resilient, creative way to keep in touch--the personal letter.


A personal letter takes longer to write than the few abrupt sentences you bang out without proofreading before you click on "send"; it takes longer to read than the blink-and-delete blitz that helps you purge your in-box; and it digs deeper than the brief handwritten note that you drop in the mail. A letter deals with issues that deserve more than a minute of attention. It aims to strengthen a relationship, not just react to a situation. A letter isn't limited to a specific message like "Can you come over?" or "Thank you for the birthday check." Rather, it can take both the writer and reader on an excursion that sets off from a home base of mutual trust: "I know you'll be interested in what I think" or "I'd like to hear your ideas on this." Whether it comes into your life onscreen or through the mail slot, the well-thought-out personal letter is irresistible to read aloud, mull over, respond to, read again, and save.

Good letter writing feels much like good conversation, and it has the same power to nourish a relationship. It even includes the same critical ingredient of taking turns, since the best way to start writing a letter is to begin where the two of you left off, by picturing your last -get--together or by rereading whatever the person sent to you. Letters allow your conversation--and your thoughts about each other--to amble along at a leisurely pace, even while other parts of your lives are galloping by.

The next time you need to connect with someone who matters, on a subject that requires more than a snap reply, stop and ask yourself, Is there a better way to do this? Is your connection as warm and strong as it could be? Think about what it feels like to settle into a personal letter that's been written just for you. Remember how connected it makes you feel, how valued and cared for. Couldn't you use more of that in your life? Whether it arrives in an envelope or on a computer screen, the personal letter is a small masterpiece in the art of staying connected.

Personal letters carry thoughts and feelings that don't come through as clearly any other way. They tap into a rich stream of history, send your reader unmistakable proof that you care, and offer an outlet for your creativity.

Even though you appreciate this lost art, you may still doubt your ability to be this kind of artist. Let's try to pinpoint what is holding you back. Is it the time involved? Are you at a loss for what to say or how to say it? Do you worry about the rules of letter writing? Although you will find in this book a wealth of guidance and ideas to get you started, remember that the aim of letter writing, like any art, is better expression and connection. The point is not to create perfect letters, but to reach out to the people you care about in a more engaging way.

The first part of this book covers the basic tools and formats, as well as fresh ideas to help you feel confident about what and how you write. The second part includes tips for writing common kinds of letters, with sample letters to inspire you to write (or type) on your own. All you need to do is focus on how satisfying letter writing can be. Like walking to the store instead of driving, you can build your letter-writing muscle by finding ways to integrate letters into your routine. Just because you can send short messages the moment they enter your head doesn't mean you have to. Start now; each letter you write will make it easier to write the next one. If you're skeptical about how to fit letters into your crowded schedule, relax. You don't have to unplug your computer and go back to hand-cut quill pens on monogrammed paper. Instead, you can learn to take the best that the traditional letter has to offer and use it to add sparkle and civility to everything you write, type, print, attach, or e-mail. This book will show you how.

Your message, of course, forms the core of your letter, but before you choose your words, you'll need to decide on the best way to present them. Does the occasion call for ink on paper, or would a nicely worded e-mail be the best vehicle to convey your thoughts? Should you print out a typed letter and mail it in an envelope, or attach it to an e-mail? There is no one right choice. Most personal letters can take different forms to fit different situations and relationships. Before you begin, ask yourself how the format you choose will affect the way your message will be interpreted. Doing this will help you to make better choices, and to appreciate and interpret other people's choices when you read their letters.

Because people can't help noticing, on some level, how you choose to present your ideas, your choice of format becomes an integral part of the message. In addition to the literal meaning of your words, the visual qualities of your format provide clues to your reader about how to interpret your letter. Your timing and your choice of materials also convey messages about your relationship with your reader. Pencil on notebook paper says "I didn't forget your birthday" to your mother, but it says "I'm really clueless" to your boss's wife. A letter written by hand on Cartier stationery suggests a stronger effort to apologize to an offended hostess than a hasty e-mail message, even when it contains exactly the same words. On the other hand, a long, reassuring e-mail letter of support that comes half an hour after your best friend has called in a crisis will do much more good than the same words that arrive four days later on paper. A senator's office staff may, as a matter of policy, give more weight to a well-worded defense of your position, typed neatly on personal letterhead and signed, than they give to a checked-off, standardized postcard--in fact, they may even show your letter to the senator. And a letter to a long-lost high-school friend will call up a clearer mental picture of you if it arrives in your handwriting on good stationery than if it pops up in her e-mail in-box.

Today there are three major ways to send a personal letter; each of them has strengths and weaknesses:
        *       You can handwrite a letter and send it by mail.

        *       You can send a letter by e-mail.

        *       You can type a letter as a computer text document. Then, you can either print it out and mail it in an envelope or attach it to an e-mail.
There's no uniform rule for how to send which words, when, and to whom. As in all art, the ideal makes compromises with the real. You might prefer to write a long letter of advice to your daughter at college to accompany the check she suddenly needs you to send, but reality may dictate that you transfer the money to her account from your desktop computer and type your advice into an e-mail attachment that she'll open right away. In contrast, your occasional letter to your grandfather may give him much more pleasure if it arrives on paper with a family photograph or a news clipping enclosed for him to share with his friends than it would if it appeared in an e-mail in-box that he seldom opens.

Learn to trust your own instincts when you choose a format for your letter. Listen to the little voice that murmurs either "Maybe this one deserves more effort" or "Don't worry so much this time; just get it there somehow." There are many ways to improve your letter, no matter how you send it. Although one format may be more communicative than another, any letter is better than no letter at all. Don't let your aspiration to come up with the perfect missive get in the way of your effort to create one that is good enough.

When you feel comfortable with the format you choose, your authentic writing voice will stay in tune and resonate more clearly. You may give voice to a different part of yourself in what you scrawl on plain paper than in what you write in your careful calligraphy on -keepsake--quality paper stock, but you're still expressing you. Just as the same two people will have a different conversation in a pizza parlor, a French restaurant, or at a church coffee hour, each form of a personal letter can bring out a different side of your relationship.

To make your letters most personal, you'll need to strike a balance between what comes easily for you and the extra effort that you can expend to make them the best they can be. Keeping this balance in mind, let's look at each format's strengths and weaknesses.
Handwritten Letters

Writing by hand sets the gold standard for making yourself truly present to your reader. Traditional pen-and-paper letters offer many unique advantages. Handwritten letters feel intensely personal, weaving together your ideas with the visual art of words, color, and texture. They offer unimpeachable evidence that you believe the reader, the message, and the relationship are worth your time and your undivided attention. Letters that you handwrite on paper not only look good; they smell good and feel good, too.

Writing by hand requires only a few widely available low-tech, low-cost materials and tools that you can use anywhere, without needing a computer, Internet access, special know-how, or a place to plug in. Physically durable, letters can be archived by the recipient and reread by anyone decades--even centuries--later without special technology. A stamp that costs a couple of quarters sends them anywhere in the country, and a dollar or two sends them around the world. People welcome a handwritten letter as an ambassador from a more civilized age, and they are ready to extend that extra courtesy to the words they read and the person who wrote them. And nowadays, sheer novelty means that the person who receives a handwritten letter in the mail will sit up and take special notice of it, and of you.

Handwritten letters do have their disadvantages, though. Their delivery can be maddeningly slow and unpredictable, ranging from overnight to a full week, with no mail deliveries or pickups on Sunday and holidays. If the address or postage is wrong, the envelope may not be returned to the sender for weeks. The reader who is accustomed to hitting the reply button may take longer--or forever--to make the effort to write back by hand. Also, handwritten text can be hard to revise and correct, writing by hand can be slower than typing, and handwritten letters may be hard to write or difficult to read. The act of handwriting itself, less a matter of routine today, makes some writers overly prim and self-conscious when they pick up a pen.

If you decide to handwrite a letter, don't let concerns about these potential pitfalls hold you back. You don't have to reach impossible standards of eloquence and beauty. If your intention is to connect with your reader in the most personal way possible, just the extra effort you put into ink on paper will be greeted with appreciation and delight.
Letters That Are Printed Out or Attached to E-mail

You can send the next best thing to a handwritten personal letter by typing your words into a document and printing them out to mail in an envelope. You can also send a typed letter immediately by attaching it to an e-mail. With some planning and good judgment, this format can offer the best of both worlds--the time and attention that go into a well-crafted letter, plus control over the timing of its delivery.

Printout letters are easy to draft, revise, save, and go back to later, and they benefit from the computer's spell-check system and grammar suggestions. If you print these letters and mail them, you can make them more personal by adding a few sentences in your own handwriting, or by making a creative statement through your choice of paper, font, point size, type color, spacing, and margins. A recipient with poor eyesight can download the document you have attached to an e-mail and enlarge the font size or zoom in closer for easy reading. In addition, you can keep a permanent copy of what you wrote on disc or in your "sent" file.

Like e-mail, however, printout letters require electricity, a computer, and a printer, and if they are sent through the post office, they will spend a few days in transit. Printout letters can turn a normally fluent writer into a nitpicking, typography-crazed perfectionist (like me!), more obsessed with margins, fonts, and dingbats than with actual thoughts and feelings. Or it can reduce the most fluent calligrapher to a two-fingered hunt-and-pecker. And despite all the care that the writer puts into typing, printing, and mailing, some readers may feel that printout letters are just too impersonal, almost commercial, as compared with handwritten ones.

Sometimes this hybrid medium feels just right, though, for both the writer and reader. Requiring only a little more time than you would spend on an e-mail message, a letter that comes from your keyboard can feel almost as personal as a letter that flows from your pen.


Excerpted from "The Art of the Personal Letter"
by .
Copyright © 2008 Margaret Shepherd.
Excerpted by permission of Crown/Archetype.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

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