The Secret Powers of Your Mailbox

A 21-Day Challenge to Improve Your Life and Leadership While Social Distancing

My fingers are stained with ink from my fountain pen today. But I’m not complaining. It’s a small price to pay to connect with people I’ve not seen in-person for a while.

In these days of cell phones, email, and text messages, writing is a lost art. But it’s worth bringing back. Because writing offers an experience technology can’t touch. Facebook and Twitter are terrific ways to tell others what you just ate. And email works for a quick exchange of ideas. But for sharing matters of the heart, nothing compares to handwritten words.

Because sending a letter is the next best thing to showing up at someone’s door.

Words crafted with your own hand hold significance. They display a deep connection to the reader. The thoughts you pen come from a place of intimacy that subtly communicate, “You matter.” There’s value to words etched into the fibers of fine velum.

In this time of social distancing when life-on-life is limited, handwritten communication is the best alternative to being in-person. With a push of a key or the swipe of your finger, digital communication is instantly deleted. But handwritten letters have the ability to last a lifetime.

There’s a folder in my desk of correspondence I’ve received over the last 30 years I hold dear. Most of these letters and notes were sent as words of encouragement. As I rifle through this file, I’m reminded of the impact of these thoughtfully written words. And I’m certain that when I’m gone my sons will read them and realize why I held on to these timeless treasures.

As I get older, I’m giving more consideration to my legacy. And I’m wondering, “Does anyone have my handwritten letters in their drawer?” Maybe a few people. But certainly not enough.

Words matter. My wife uses that phrase constantly. Cindy is always writing to people. She never misses an opportunity to put her thoughts on paper. Because she never wants anyone to ever wonder how much they meant to her. So today, I’m taking a lesson from her playbook.

This morning I took out a stack of personalized notecards and envelopes from my desk, filled my pen with fresh ink, and made a list of people I care about deeply. Then I lit my favorite pipe and started to write making sure to share my heart with sincere and honest words.

My desire to help people live and lead with authenticity in an artificial world requires that I continue to create healthy habits in my own life. But I want to encourage you to join me. So I’m offering a challenge to help you improve your own legacy as well.

Write at least one handwritten note or letter to someone for the next 21 days.

I still open the mailbox every day in hope of finding more than bills and credit card applications only to be disappointed with what I find. But then I remember my mom’s words when I was a kid, “If you want to get mail, you need to send mail.” That is still true today.

But perhaps we haven’t written a letter in so long we have forgotten the format. No, really? This used to be taught in school—I don’t know if it is anymore. So just in case you need a refreshed since snail mail is no longer favored, I’m going to offer some instruction below.

My hope is that you will give serious consideration to my thoughts and take me up on this simple challenge. I am confident that it will enhance your own life and leadership while it creates lasting memories and impressions on the lives of those to whom your write. If you’re up to the challenge, please click the button below and tell me!

I'm taking the challenge, Tim!

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Tools and Techniques


As I mentioned earlier, writing is a lost art. And art requires tools and techniques. A couple of years ago, I designed my own notecards and envelopes (see pic at top). I chose notecards over stationary simply because it requires fewer words. This isn’t easier or a shortcut. Saying something meaningful is harder when you have less space.

If you’re interested in creating you own notecards, you can download the free design files here. I’ve included multiple formats to make it easier. If you go this route, I suggest you use I’ve never found better printing for a better price.


Again, I mentioned that my preferred utensil for writing letters and cards is a fountain pen which requires practice. There’s something unique and sophisticated about using this tool for writing. But you should use the pen that’s most comfortable in your hand.


Since I send notecards, I don’t always follow conventional rules for writing letters. But I thought I’d refresh your memory on the standard five parts of any letter:

  1. Date
    I like to add the date to my correspondence regardless of format. People may search their folders of warm fuzzies someday and wonder exactly when you sent that gem.

  2. Greeting
    I’m sure this seems like common sense, right? But in our informal society, it think it bears mentioning that it’s best to use a person’s name instead of saying, “Hey, Dude!”

  3. Body
    I don’t write lengthy messages. I’m more concerned with quality than quantity. In order to utilize the space best and keep from making mistakes, I practice on scratch paper.

  4. Closing
    I believe this element of the letter shouldn’t be taken lightly. Over the years, I have used different closings. Today, I sign 99% of every correspondence with “You’re Not Alone!

  5. Signature
    I think a person’s signature is sacred. When I receive a signed letter, it holds weight. If I get unsigned correspondence, I typically throw it in the trash. Always sign your letters.

Square Peg Round Hole™ with Timothy Eldred is created to help you live and lead with authenticity in an artificial world. Subscribe now for free for this blog and podcast below. To learn more about the mission of Square Peg Round Hole™, please go here.