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

by Margaret Shepherd, Sharon Hogan

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.

Genres: Nonfiction, Writing, Reference, Personal Development

218 pages, Hardcover

First published January 1, 2008

Reviews

[Jaima · Rating 3 out of 5]

I didn't want to read this book--and fully expected it would be one big guilt trip. I gave up writing letters long ago, and am immune to laments about the death of snail mail. In the end, I couldn't resist the pretty cover.
It's not surprising that Ms. Shepherd, a calligrapher and inveterate letter writer, has made her book so beautiful. She covers every letter-writing topic you can think of: pens, papers, typefaces, envelopes, and this attention to detail is reflected in the volume itself. It is a perfect size and a pleasure to hold, with the right paper weight. I believe Ms. Shepherd refers to it as the kind which kisses your fingers.
In pleasant, conversational prose, Ms. Shepherd delves into the nitty gritty of correspondence: emails, printed letters, the annual Christmas letter, how to write a love letter or a Dear John. She also includes real examples of each, which I must admit I rather enjoyed. I won't examine the reasons why I get such a kick from reading other people's mail.
I didn't feel guilty once, and I have written an astonishing six letters since I finished. Just because I wanted to. Two were email missives and four were handwritten with a fountain pen (my love for my Lamy predates this book). All came easily, thanks to Ms. Shepherd's expert advice.

[Amy · Rating 2 out of 5]

This was a fast read because a lot of it was skimmable. The first section is a very basic introduction for someone who has never considered writing a real letter before. Since I was hoping this book would help me improve upon my letter-writing which I've been doing for over twenty years, that part was far too basic for me. The most useful sections of the book, I think, are those which give advise about specific kinds of messages. The break-up letter, letters of condolence or sympathy, etc.

[Madie Anderson · Rating 4 out of 5]

This book is a reminder to reinvest in your relationships the old-fashioned way. It's a light read, and there's no need to sit down and read it all at once, but it is a good reference to turn to when drafting something tricky, like a letter of condolences.

[M. H. · Rating 4 out of 5]

This is a skim-as-needed book. Useful reference material, poor straight reading material.

[Caroline · Rating 4 out of 5]

Great ideas! :)
I'm inspired to write more letters for my love ones!

[Shorel · Rating 5 out of 5]

To cure the sick heart, I'm been diving deep into the word of God. To facilitate that goal, I've taken up calligraphy to practice writing out scripture...and improve penmanship. As long as I'm at it, I figure I can start writing letters. Yes, old-fashioned, folded into an envelope with a stamp on top...letters.

However, I don't know how to write letters. I learned the mechanics of letter format, but not how to craft the content.

This book went not only into the tips and tools of letter writing, but also the content of a number of different types of letters: Apology, congratulation, condolence, sympathy, advice, love, holiday, etc. Each type of letter gives an example of how it would be written. VERY helpful advice for the socially challenged like myself.

I particularly appreciate the author's consideration of modern communication media (email, social media) in light of relationships. How modern media may be more appropriate for time sensitive subjects. In other words, when someone might need an email now, versus a letter a week from now.

Armed with this knowledge, I look forward to regularly practicing my correspondence!

---
Quotes:
Take pains and pleasures in constantly copying the best things you can find done by the hand of great masters…. Then you will find, if nature has granted you any imagination at all, that you will eventually acquire a style individual to yourself, and it cannot help being good; because your hand and your mind, being always accustomed to gather flowers, will ill know how to pluck thorns. —Cennino d’Andrea Cennini (c. 1370–c. 1440)

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 560-564


Don’t let your own impossibly high expectations keep you from writing by hand. A study by the Pilot pen company a few years ago showed that most people judge their own handwriting much more harshly than they judge other people’s.

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 597-598


Confine yourself to one P.S. only! A second P.S. makes your thoughts seem fragmented, and a third means you should write a second letter after you have gathered your wits.

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 892-893


Somewhere between the great letters you should write and the daily messages you actually do write, you can spend a few minutes on the good letters you could write. A letter adds one more strand to whatever cord already connects you to others. It lets you develop a conversation that’s slow, deep, and strong. You’ll feel closer to people far away and stay up-to-date with those you see only now and then.

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 948-951


CHOOSING THE RIGHT WORDS • Paint a word picture with small specifics rather than vague generalities. “I thought of you when a little boy caught a pop fly at the game last night” brings the reader into your life more vividly than “We’ve sure had a lot of good times together.” In Writing Gooder, Rhys Alexander wrote, “Detail makes the difference between boring and terrific writing. It’s the difference between a pencil sketch and a lush oil painting. As a writer, words are your paint. Use all the colors.” • To get started, try one of these phrases: “I was just thinking…” “Something you said reminded me of…” “I’ve noticed something that might interest you.” “I forgot to tell you…” “It’s a beautiful day here. I thought you’d like to hear about what happened in our orchard last night.” • Instead of the trite “How are you? I am fine,” ask questions that show genuine interest, such as “Are you back on your feet?” or “I’m halfway through unpacking.” • Be direct. Say, for example, “I wanted to ask how Janet’s recovery is going” rather than just beat around the bush by asking, “How are things?” • You don’t really need the filler phrases “for your information,” “if you’ll excuse my mentioning it,” “no offense, but,” or “by the way.” They make you sound reluctant to write what’s on your mind. • I is good. You is better. We is best. Use all three. Consider the difference between “I want to be sure you were aware of all the compliments about Juanita’s party. We saw the Ryans yesterday and they were raving about it” and just “Great party!”

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 981-994


RULES OF THUMB FOR WRITING A LETTER HOME Begin your letter by greeting the reader with warmth, locate yourself in a specific place, and include the complete date. Next, mention news about places and people you have encountered, and send greetings to others as well as to the reader. Don’t complain, dwell on the transitory, raise problems without suggesting solutions, harp on things that can’t be fixed (like the realities of the separation itself), or even mention the kind of problems that are going to be solved before the letter arrives (such as lost sleep, minor aches, and moods). Likewise, don’t mope or drop verbal bombs. Frame any difficulties in possible solutions. There’s no need to repeat over and over how much you miss the people at home; this will undermine an adult’s morale, drag down a teenager’s normal steps toward independence, make a parent feel guilty, and upset a child. As Shakespeare wrote in Macbeth, “Things without all remedy should be without regard.” Give the reader specific details about your impressions of the places you’ve visited, the people you’ve met, and the ways in which these new experiences have transformed your way of thinking. Last, reaffirm how connected you feel with the reader.

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1016-1027


CHOOSING THE RIGHT WORDS • Make associations between your world and the world of your reader. For instance, “I took a picture for you of a pub called Kiernan’s Alehouse when I was in Ireland last week. The same spelling as your son’s name!” • Expand the connection by mentioning others: “Tell Mom that the scarf she sent has kept me warm all over Minnesota.” • Reflect on the effect that your journey has had on your worldview: “I never really appreciated how frustrating the language must have been for Yu Yan when she first moved to Texas until I visited that village outside of Qufu, where not a single soul spoke English.” • Underscore the strength of your relationship when you conclude your letter. As one nineteenth-century traveler wrote home, “If I were with you, I could talk enough to tire you.”

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1045-1052


To send a letter is a good way to go somewhere without moving anything but your heart. —Essayist and teacher Phyllis Theroux

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1058-1060


Good friends are hard to find, harder to leave, and impossible to forget. —Anonymous

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1123-1124


RULES OF THUMB FOR WRITING A “KEEP ME ON YOUR RADAR” LETTER At the beginning of your letter, reintroduce yourself and remind your reader about who you are, and were. Mention the nature of your old connection. Next, describe where you are now, both in your life’s journey and on the physical map. Also, inquire about the other person’s life at present. Express a wish for a continued or renewed connection. If you have an ulterior motive, it’s usually best to be frank right away. I learned over the years that one of my acquaintances only wrote me to “get back in touch” when she needed a convenient place to stay on business trips; my recollection of feeling used has kept me from making the same mistake with my own old acquaintances, whom I keep in contact with solely for friendship. Just as you would in an actual conversation, don’t spill too much information right off the bat. Don’t be too explicit. If you view this person as a confidante but she can barely recall who you are, your instant intimacy may put her off. In closing, convey good wishes, and provide clear contact information for a reply. If you’ve proposed reconnecting once and received a neutral or frankly negative response, admit to yourself that the other person may just not be interested in resuming your relationship. MAKE IT PERSONAL Handwriting on stationery paper is a good cure for neglect. If you’ve let time slip by, show that you are making up for it now by taking time to write by hand. If it’s been months or years, you don’t need to save another three days by firing off an instant e-mail, except to inquire about an up-to-date mailing address. What your reader sees and touches will remind her of you, so choose ink and paper that expresses who you are. Dress your words with the same care you’d use in selecting what to wear to meet someone after you’ve been apart. Without turning your letter into an art project or a formal document, show that you value the relationship and the other person’s time. CHOOSING THE RIGHT WORDS • Use sentences like “I would like to get back in touch,” “Let’s catch up,” or “It’s been a long time.” • Leave until later the statement “I miss you.” Instead, “I miss our friendship” or “I miss seeing you” may be more appropriate. The other person may have changed, or the situation may have changed. • Don’t leave the next steps vague with offers like “We must get together sometime.” Offer a specific proposal that is easy to say yes to, such as, “Are you free for a cup of coffee at the Student Union any Tuesday in March?” Then offer an escape hatch that permits a graceful no, such as, “If this is not convenient for you, let’s stay in touch and try again in May.” Don’t put the person on the spot with forced choices. • Never ask for an apology after a long silence. Be the first to offer one, if you think one is called for at all (it usually is not). If you think your apology would help thaw the ice, read chapter 22 on how to say “I’m sorry” in a personal letter.

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1131-1157


Adjectives such as fun, fabulous, exciting, prestigious, phenomenal, successful, and incredible don’t give the reader anything to take pleasure in beyond your pleasure. They can shut your reader out and even cause a twinge of envy. If you can describe what it was that gave you pleasure, you’ll share the benefits with the reader: the sounds and smells of the Marrakesh markets you visited, the smiling ten-year-olds at the Little League awards ceremony you attended, or the theatrical atmosphere at the dog show where Rufus won the prize for “Best Mutt.”

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1250-1253


The longer your letter, the fewer people you should send it to. Send a half page if you mail to more than one hundred people. Send a whole page if you mail to fewer than one hundred people. Send two pages only if you limit your list to the two dozen people who know you well.

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1274-1275


group. Prune your mailing list twice a year: first, right after the holidays, to check whose addresses to add, remove, or change, and then again in November, to add a few more corrections and estimate how many letters to mail. Reducing the number of people you mail to will free you up to personalize what you send to the people who really count.

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1278-1281


Flatter me, and I may not believe you. Criticize me, and I may not like you. Ignore me, and I may not forgive you. Encourage me, and I will not forget you. —Pastor, scholar, and author William Arthur Ward (1921–1994)

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1453-1455


RULES OF THUMB FOR WRITING A THANK-YOU LETTER Start off by mentioning the gift by name, and describe how you benefited. Give details about the gift he gave or the reward he helped you get.

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1920-1922


Acknowledge your indebtedness but don’t exaggerate. Be lavish but not melodramatic. Psychologists talk about the “tyranny of the gift,” when the recipient can’t ever be grateful enough; there’s also a similar “tyranny of the thank-you,” when the gratitude is inflated out of proportion to the giver’s intentions. The reader will be most interested in your gratitude, not your unworthiness or your lateness. Add details about your own life, plus news, plans, and opinions. Then allude to your ongoing connection with the reader, and close with warmth. MAKE IT PERSONAL If your gratitude is worth a letter, it’s worth a good-looking letter. Choose materials that are either fine and formal or warm and cozy, depending on the nature of your letter. Avoid arty and idiosyncratic paper or comic note cards. Use white or off-white unlined paper that is slightly smaller than standard business stationery. Don’t write a personal letter on your employer’s stationery or stamp it through the postage machine! Print it out in pleasantly readable black type, or handwrite it with black, blue, or blue-black ink. One roommate writes to another with the sort of appreciation that could have been expressed aloud but which packs an extra punch on paper. Your materials should be age-appropriate for both you and your reader. Well-chosen paper and ink can show respect to your elders, speak the language of your peers, or catch the fancy of the small fry. For a lasting monument to gratitude, use ink on good stationery. Even the best e-mail suggests you are cutting corners for your own convenience. E-mail is too offhand, and a printout letter is often too impersonal, for a task that demands evidence of sincerity and effort. Do, however, send a printout letter when you thank a friend who has gone to bat professionally by writing a letter of recommendation for you.

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1923-1939


Most personal letters rest on the assumption of an ongoing connection. If you are writing to thank a person (such as an interviewer) for simply doing his job, send a short business note, not a long personal letter about yourself and your dreams. CHOOSING THE RIGHT WORDS • Say thank you on paper with many of the same words you would use in person if you could have an hour over a cup of tea or coffee to talk and catch up. Use words like grateful, kind, glad, thanks, thank you, thankful, and appreciate. • Praise the reader’s kindness specifically. Write “You are so thoughtful!” or “You made me feel so welcome,” rather than “You are such a great person” or “That was a wonderful present.” • Share your delight and acknowledge the giver’s role in making something possible for you: “Thanks to you and your letter of recommendation, I got hired right away—only six days of nail biting and stewing. Then they needed me the next day. I am already finding that the skills I learned from watching you with a classroom full of four-year-olds are very useful when I deal with fourteen-year-olds.” • Write “I hope I can help someone else the way you have helped me” or “Thank you from the bottom of my heart,” rather than an obvious exaggeration such as “You’ve saved my life” or “I owe you my firstborn.”

Margaret Shepherd and Sharon Hogan, The Art of the Personal Letter: A Guide to Connecting Through the Written Word, loc. 1945-1956

[Jary Welker · Rating 5 out of 5]

I was gifted this book a number of years ago and loved it the first time that I read it. With the growing tsunami of ways to "communicate" in our social media age (much of it not very 'social') the time tested art of writing a letter may still be the very best way to stay in touch - really in touch - with those that are important to us. From helping us find just the right words, ink and even paper Margaret Shepherd helps us find the best way to put words on paper. Whether it is a note to an old friend, a letter of condolences, congratulations or even an apology, it is filled with examples and instructions on how to say the right thing in the right way. As was true in the 19th century of the spoken word is certainly more true in the 21st of social media, as the author cites Emerson in her case for writing more letters;

'The tongue is prone to lose the way,
Not so, for in a letter
We have not better things to say,
But surely say them better."
- Ralph Waldo Emerson

[Michael · Rating 4 out of 5]

Many people find writing letters cumbersome by having to find a piece of paper, address and stamp. Or intimidating because they don't know what to say....properly.

This book takes away the latter issue because the author gives some really useful 'templates' on how to write, say, a "Thank You" letter. Or what to write to someone whose loved one has passed away (a "Sympathy" letter.) Or even a letter on trying to hook up again with a long lost love "a "Can We Try Again?" letter).

As for those lazy people who don't mail personal letters because they don't have paper, they should definitely go out and buy some proper cards (which the author gives some great tips on) and have stamps on hand. Your personal relationships will definitely improve when selflessly sending out missives to those you like, love, or respect.

[Alexandra Beckett · Rating 3 out of 5]

3.5 stars. The book felt a little dated with some of its templates and ideas. However, I really enjoyed reading about the history of personal letters and how you can put your personality into a personal letter from choosing the paper (texture, weight, and even scent!), to the handwriting, the type of envelope you choose and the stamp. Because of this book, I have put a lot more thought into choosing beautiful stationary, stickers, and stamps and try to make it a point to write a personal letter when I can to say thank you, congratulations, or just a thinking of you letter.

[Annie · Rating 3 out of 5]

Her warmth for the old art of letter writing is sweet and her examples of different kinds of personal letters are mostly just adequate. For the example of a love letter, however, she includes one that Ronald Reagan wrote to Nancy on an anniversary that they spent apart. "It's time to move on to the next town now and every move is a step toward home and you. I love you so very much. I don't even mind that life made me wait so long to find you. The waiting only made the finding sweeter."

[AlohaKarina · Rating 5 out of 5]

If you grew up in a generation that didn’t write letters, and you don’t know how to write letters, this is an excellent primer on how to do it. I found myself in agreement with a lot of sentiments such as when you’re writing letters to somebody else, don’t tell them that you feel this or make it about you. It should be about them. That’s something I’ve learned over time. I can strongly recommend it. It was well-written!

[Bethany · Rating 2 out of 5]

Vaguely interesting but a bit dated (I couldn’t believe the idea of using a pdf for attaching to email was never mentioned, but maybe that is just newer). Maybe good to have as a reference for the wording to choose in different types of letters but it didn’t really add anything to my stores of ideas for pen pal style letters with friends.

[Leonard · Rating 5 out of 5]

Good solid advice on writing personal letters. I'll reconsulting this again in the future.

[Heather · Rating 3 out of 5]

While this book may not have been as useful for me, I know many readers will find it a useful resource.

[Linda · Rating 4 out of 5]

Full of useful suggestions and facts about the history and art of writing letters. Includes some sample letters. A bit repetitious at times, which lowered my rating.

[Kristy Buzbee · Rating 4 out of 5]

A sweet little book with some nice ideas. I'm trying to get better about writing my thoughts to others, and writing more than a sentence in cards.

[pea. · Rating 2 out of 5]

if you received a letter in pencil written on the back of a receipt would it mean less than one written on monogrammed stationery with a fountain pen?

think on it and send me a letter.

[Katherine · Rating 4 out of 5]

Great tips for a wide variety of situations where you'd need/want to write a letter. Good for a newbie or someone looking to double-check or refresh their etiquette.

[Angie · Rating 4 out of 5]

Synopsis: "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."

My Review: I read this book, as it has become my 2013 New Year's Resolution to write a letter to one of my friends and loved ones each month. I was expecting a dry, instructional read but was pleasantly surprised how interesting and fun Shepherd made the book. I have so many pages marked, selections highlighted and notes written in the margins. While this was more of a refresher for me, I did find a lot of useful information. I really loved the chapters towards the end about applying the personal letter to specific situations ranging from break ups, condolences and fundraising! There is so much helpful information packed into this book.

[Emily · Rating 3 out of 5]

For someone who has written a fair amount of letters this was rather a nice read. It goes over the basics of materials, combinations of colours, paper weights, types of paper to use, the best types of pens to use, and that is just the beginning. She then goes into how to write the actual letter itself, which may seem intuitive-and in some sense it is, to show how you plan to write it and the considerations you give to the reader. The most helpful sections were the individual chapters on how to write those tricky letters: condolences, sympathies, congratulations, advice, apologies, and so on. It is skewed towards handwritten letters over typed or emailed ones, given the author's background it makes sense. This is a book for someone who wants to learn more about letters, write letters, or who just has a fondness for paper and the art or writing.

[Duckpondwithoutducks · Rating 2 out of 5]

I love writing letters, so I thought that I would find this book very interesting. But, it is more for someone who has never written or read or received a letter before - somebody who needs the absolute basics on how to write a letter.

[Troy · Rating 2 out of 5]

THis was...meh. I did appreciate the different types of letters presented here. It's not a bad book; inexpensive and small and very supportive of you getting off your ass and writing a letter, but just okay.

[Leif · Rating 3 out of 5]

Basic advice, but detailed, thoughtful, and organized. A good primer for young adults perhaps, or those completely new to letter writing / people who need a brief refresher for a certain type of letter – Sheperd writes in detail about 19 different kinds of personal letter!

[Jan · Rating 4 out of 5]

Has some good ideas when I need a little inspiration for those "I need & even want to write a letter" but am having a hard time getting motivated to actually sit down and put pen to paper.

[Megan · Rating 4 out of 5]

Thorough, simple, and straightforward. And inspiring.

[Jennifer Medina · Rating 3 out of 5]

Good information for people who are new to writing letters, but unfortunately it includes nothing about getting started with a penpal.

[Krista Phipps · Rating 3 out of 5]

A very good reference when you're trying to make that correspondence extra special.

[Katie · Rating 2 out of 5]

dissapointing...really not all that interesting.