The Lost Art of Letter Writing & the Role of Guilt in Resuscitating Snail Mail

Letter Writing: Who’s Got the Time?

Whether you’re old or young, centennial or millennial, a discussion of the art of letter writing requires facing some hard truths and lost skills. Among them:

  • Writing: Whether you’ve been swiping and typing since pre-school, or arthritis has put pen-gripping in the rear view mirror, writing legibly in cursive (or print, for that matter) is a challenge for many. (Side note: National Handwriting Day is January 23rd—a good time to brush up?)
  • Spelling: Who among us (English teachers and standardized test takers aside) can say they’re comfortable forming a sentence without auto-suggest?
  • Mailing: How does one get hold of a stamp? Where’s the closest mailbox—those are the blue ones, right?

Add to this list a host of further plot complications, including cards, envelopes, and what the heck to WRITE, and you see why the art of letter writing is referred to as lost. But wait. Not. So. Fast.

Like refurbishing a piece of old furniture or starting a home vegetable garden, there’s a time and place for “slow living” and snail mail may well be the poster child for this lifestyle trend.

Advantages and Disadvantages of Writing Letters

Letter writing is about slowing down and taking deliberate, thoughtful action. But deliberate work is tough and not without its drawbacks. Let’s explore the pro’s and con’s of letter writing in a realistic manner, leaving aside any waxing poetic references to the letters of Louisa May Alcott, those from Christopher Columbus to his patrons King Ferdinand and Queen Isabella , or those between Emily Dickinson and Thomas Higginson. Letter writing is for everyone!


  • Let’s Not Belabor the Point: Dashing off a “thank you” can often be done most effectively via text, email, or phone. Text a quick, emoji-filled THANK YOU to your friend for driving you home after a big night out and knock that action item right off your list so you can get back to napping!
  • It’s Happening Now, Folks: If you’re hosting a last-minute potluck at your place, there’s no time to involve the government in guest communications and RSVPs.
  • Evidence? No Thank You: When it comes to gossip, a paper trail is undesirable. If you can’t talk in person, Snapchat or similar is your next best bet. Letter writing is out. Way out.


  • Unsend! Unsend! Because “backspace” and “delete” aren’t options in letter writing, you’re more likely to think through a thought before writing it down. This alone is soothing to the modern mind, zipping as it is up and down the rabbit holes of email, text messages, and all things web-enabled.
  • Sign Here, Please. A letter in your own hand carries with it an air of sincerity, a kind of personal endorsement that Helvetica, Times New Roman, or Arial Sans Serif just can’t impart.
  • No Action Required. At least not immediately. Unlike text or email, the timeline for response to a letter is weeks, months, a year—or sometimes never. Phew!
  • You Like Me! You Really Like Me! A handwritten letter makes your recipient feel special. This is the most important aspect of letter writing—whether it’s to your gramma, your colleague, or your potential prom date.

Letter Writing: Use Sparingly!

Letter writing has some strong pro’s, but no need to overdo it. Don’t let your handwritten letter be as formulaic as grocery store circulars and refinance offers. Yes, put pen to paper for that first client—the one who took the risk, believed in you, and signed on the dotted line when you were just starting out. But no need to send a thank you note every time your customer drops off their dry cleaning. A good rule of thumb: if you’re rushing through your thank you note, don’t write it.

Reviving the Dying Art of Letter Writing: The Magical Power of Guilt

Wondering if you owe your great aunt a thank you card for the homemade pralines she sent you for Christmas? Wondering if your godchild will need therapy because you’ve never written him a birthday card? Wondering if the client who shared a personal loss with you during your last meeting could use a sympathy card? The answer to these and similar questions is YES.

Make some tea, coffee, or a stiff drink. Light a candle, light a fire, or turn on a bright fluorescent light—whatever makes it less painful to sit down, write down some thoughts and ideas, and share them with someone who might benefit. Could be your Mom, your neighbor, your longest-term client or your newest customer.

As a reluctant letter writer myself (I logged two in the past year), I can attest to the fact that the byproducts of the act include assuaged guilt, accidental calm (yoga next!), and an unwarranted feeling of self-righteousness that can’t be beat. And on the recipient’s end, there’s relationship enrichment and customer retention.

Bottom Line: Let guilt be your guide. If in doubt, send it out!

A Few Suggestions from a Promotional Pen Company

Whether your foray into letter writing stops at the posting of a single letter, or the acquisition of an 18th century secretary desk and fountain pen, you’ll need a few things to get started:

  • Pens:
  • Cards: Grab a few blank ones at the grocery store or bookstore to have on hand. Also, keep a box of customized greeting cards at the ready so you can easily post a card to a customer, colleague or friend.
  • Stamps: We don’t sell stamps but the USPS does. And they’ll deliver to your door, along with other basics like envelopes and blank cards.
  • Low Expectations: Despite the nostalgia attached to the pastime, letter writing doesn’t have to be intimidating. The charm is in the chicken scratch, fits and starts, disorderly paragraphs and run-on sentences. The appeal of letter writing is that it offers an unedited look into the sender. A few misspellings and dangling participles only serve to connect you further to your reader!

We hope you feel the art of letter writing is ever so slightly more accessible, an easy way to tamp down guilt, and a good way to slow down. Perhaps you’ll dip a toe into the letter writing waters on National Letter Writing Day (December 7). Enjoy the pace!


P.S. For a deep-dive into handwriting, check out our What Does Your Handwriting Say About You blog?

Karleen Wise Andersen

From marketing tips to product recommendations, I’m here to help small businesses be their best.

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