Three Steps to Writing Thoughtful Letters this Holiday Season

Before 2020, 40% of Americans reported feeling lonely, a condition that the surgeon general has warned is more deadly than cigarette smoking. That’s not me being an alarmist. Our bodies just crave—need—human connection for healthy living

Imagine that 40% of the population now, in 2020, working and living from home. Some might actually feel more connected with others. People have time to reconnect. But the reality is that part of that sense of isolation came from the very things—virtual connection—that we must rely on now even more than before. This means that the mounting sense of isolation is only getting worse. 

As we enter the season of writing letters and messages, of greetings and well-wishes, how do we craft a message that can possibly warm the hearts of those that receive it in all cases? How do we wish people happy holidays in a year where “happy” is a word that does not universally resonate? 

First, I want to acknowledge that your concern about what to write is completely valid. We’ve diminished the importance of what we say for a long time, starting with the old adage that it’s only the sticks and stones that we need to fear. In fact, researchers found that after reading a personal letter that included positive things written about them, humans experienced sensations of warmth that were neurologically the same as experiencing physical warmth.  The temperature achieved in the body from the letter likens the warmth the human body feels from an actual hug, meaning we feel the same type of connection from words as we do from the positive physical connection. 

This is powerful information: it means that our words are, in fact, as powerful as our bodies. Even from a distance, even in this COVID-limited world, we can use our words to create the sense of our presence in another person by how we write our words down. 

And I am going to show you the fail-proof way to do that. 

Step 1:
Start with Context


Usually, we begin our holiday greetings with standard summaries of all of our achievements. At times when we can plausibly assume that the world was many people’s oyster for the last 365 days, this can be appropriate. 

Not this year. Not a year when so much loss, fear, and loneliness has been felt. 

Instead, start with a visual representation of your context. Tell them about the realness of your place. This is NOT the same thing as listing your woes or worries. It’s giving people a way to walk into your world. 

Here’s what I mean. 

Your past holiday card might have begun with something like this: 2019 was such a busy year! Jane finished her senior year on the honor roll, and we all drive to Florida to celebrate her achievement. 

This year, you might begin with: I’m sitting here thinking about you this holiday season from my kitchen, where I’ve been working for the last seven months like so many of you. 

Why this? Your holiday card is going to be meeting three groups: 1) those who have experienced more hardship this year than you, 2) those who have experience equal hardship, or 3) those who have experienced less. Your entry point of context allows your readers to begin to process where you are without asking them to bear the load or feel defensive. You’ve started with story, and story is powerful. 

Step 2:
Tell a Story

Most holiday cards are a recounting of the year, but that probably will not feel right to you this year. It’s either loudly shouting you’re okay or putting a lot of worry on a community that’s already worried. 

This is the year not for holiday greetings and updates but letters. Real letters that tell stories. 

This year, instead of sharing about your year, tell between one and three great stories that focus on what you’ve missed, found to be most important, or how you’ve survived. 

Example: After a decade of hating the endless driving to sports games, I’ve missed it this year. The kids screaming in the background. The neighbor kids leaving their bags in the car every time. 

Example: This year, I was finally able to read a stack of books I bought the last time I was in a bookstore (when was that even?). Three have become absolute favorites, and I’m sharing here the best tidbits because they made me laugh and cry and feel okay for a bit. I thought they might help you all too. 

You might consider different copy for different groups, or even for specific families. This would allow you to articulate to them more specific things you’ve missed. 

Step 3:
Share Why This Story Was Important Or What You’ve Learned

By sharing a story of how the year has impacted you, you’ve provided a subtle update (we’re all largely okay) while also sharing from a place of empathy for those who have faced greater challenges. 

It is from this place that the close becomes extremely important. The last element of your letter is to share why your story is important to you. Have you found yourself more grateful for friends? Has it made you refocus on what’s important including the person receiving this letter? 

Speak from the heart with an authentic connection. 



Example: When it all ends, know that I’m going to hug you closer and laugh harder. Glad for the phone calls, but nothing beats seeing all of you in person. 

Any letter written in this way does some powerful things. It allows raw honesty without creating emotional burden. It is written in a way that allows for empathy while also remaining hopeful. And for those who might be struggling most, it presents a “hero’s ending,” which is to say that it is inspiring and aspirational. It comes with hope. Hope of connection and normality. Hope of an end to whatever struggle they are currently facing. 

And that hope is the greatest gift you can send this year. 

For the most important letters this year


If there’s a special letter on your list that you need to make a truly significant contribution to someone, send it using the language of flowers. By creating a visual representation of your words in flowers, you add to your letter all of the incredible benefits therein. Flowers are known to improve depression and make people more likely to reach out to others. 

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