Why I write a newsletter (and you should, too)

Photo by Solen Feyissa on Unsplash

I started publishing my newsletter The Dann Chronicles in October of 2020. For those on the receiving end, that first newsletter may have seemed out-of-the-blue. But for me, it was a long time coming.

By then, I already had a fairly sizable email list (~500 people) from my days running my old blog Novice No Longer. I added emails of friends that I had collected over the years, and I certainly had a healthy start.

But honestly, the size of my list is meaningless to me. If you’ve read my newsletter, you know I’m not trying to sell anything. There are no sponsorships or even ways to tip me or otherwise give me money (aside from my shop, which exists largely as a joke).

If I’m not driven by money, nor am I focused on growing the size of my list, then what keeps me creating?

There are many reasons I sent that first email, and even more that drive me to craft a new newsletter each month. It’s been almost two years of monthly output now, so I wanted to take this occasion to reveal some of my motivations. Maybe it’ll encourage you to launch your own newsletter (or something similar).

It’s a great way to stay in touch with people

Most of my life, I’ve been notoriously bad at remaining connected with people. Worse than most, I’d argue. I’m only really in touch with one single person from my high school (not even my year), and not a single soul from college, despite being fairly social throughout both. Likewise, nearly a decade went by after graduation where I had a good amount of friends, nearly all of whom I’m not in contact with anymore.

The lesson I’ve learned, now that I’m in my thirties, is that holding onto friendships takes dedicated work. That is probably super obvious to most people, but for some reason it never even crossed my mind.

I enjoy socializing, but after a big party or group event I need some time to myself to recharge. That’s why I consider myself an introvert — not because I avoid social activities but because they take energy to enjoy, rather than giving me energy. Quiet nights at home leave me feeling refreshed, not isolated.

Being an introvert, I enjoy being invited to events, but it never really crossed my mind to host an event. The energetic arithmetic just didn’t make sense. But that also meant, sadly, that I was at the mercy of others 1) organizing plans and 2) inviting me. And if that’s one-sided for long enough, like it was for oblivious me, it eventually stops. And thus, no deep lasting friendships.

I’ve found, however, that a monthly newsletter is a great way to stay in touch with people. It puts you directly in the inbox of people you like, serving as the potential spark of a new conversation.

I love connecting with friends that read my newsletter and hearing which topics stuck out in their minds. Our conversations often have a deeper sense of intimacy that wouldn’t exist if there had been zero contact in-between our last meetings.

A newsletter definitely should not completely replace the effort you put into maintaining friendships, but it’s a fantastic compliment to the phone calls, text messages, and activities required to stay in touch.

It’s a way to process your thoughts

Writing helps pinpoint the exact weaknesses in your understanding of a concept. Start writing and you’ll quickly discover which parts of a topic you don’t know as well as you thought you did.

My newsletter is more than just a collection of links. There’s always a reason why I choose to share something, and I work to communicate that in the newsletter.

But that why is not always obvious to me, if you can believe that. It seems counterintuitive — you’d think that if I want to share something then I must know why — but that’s not always the case.

There’s a skill required to explore and process one’s own thoughts. Writing a newsletter is almost meditative, in that sense. I’ll have the urge to share something, and then have to do the work required to figure out why I have that urge.

With time, this gets easier. A monthly newsletter forces you to flex that muscle regularly, resulting in a better ability to think deeply in all aspects of life.

They’re love letters to your future self

As I mentioned previously, the newsletter is a fantastic way to stay connected with people. But my not-so-secret secret about my newsletter (and all my social media posting) is that it’s not about you, it’s about me.

As I’ve written before, nearly all my publicly posted content is for my own consumption later. I use the app TimeHop every morning to browse every picture I’ve taken and tweet I’ve made on that date each year in the past. I regularly re-read my annual Year in Review posts to try and ascertain how past thoughts and achievements can help me be better today.

My newsletters are a personal time capsule that I’m sending to myself each month. My subscribers will likely just read it once before moving on with their lives, but I keep them all in a safe place for future consumption.

If I’m feeling particularly nostalgic, I have a treasure trove of content to pour through. I can read my very first newsletter and my mind will instantly transport back to peak pandemic, along with all the thoughts, worries, and hopes I was mulling over at the time.

For me, the idea that content created today will become a gift for my future self is a big motivator. So much of our lives and day-to-day thoughts are ephemeral. It’s reassuring to know that I can preserve thoughts that will bring joy to my future self.

It helps people see new elements of your personality

We collect friends, acquaintances, and colleagues from different parts of our lives. We choose which aspects of our personality to reveal to each person, depending on the context of that relationship. Your work friends will see a different version of you than your brunch friends, just as old childhood friends know a different you than friends made in adulthood.

A newsletter is a way to share a larger portion of yourself with a wider audience. Colleagues have described my newsletter as an “ah-ha” moment for them, realizing we had more in common than what was revealed in a business setting. Acquaintances have reached out after realizing that we had shared passions that have never come up in conversation. Even close friends have told me about learning something new.

Even if people don’t read the newsletter regularly, for me the mere fact that it exists is an indicator of a rich inner life. It allows both strangers and non-strangers alike to think of you as a multidimensional person, rather than just a name scrolling by on social media.

Helps balance out your input/output ratio

I think a lot about my own personal input/output ratio. I don’t want to be just a mindless consumer: watching TV/movies, reading articles/books, playing video games, etc, without giving back to the world in the form of some type of output.

I don’t consider myself a typical creative type. I wouldn’t describe writing as an essential part of my being, nor am I drawn to it in the way many authors describe. Instead, it’s all about maximizing enjoyment — I find myself enjoying consumption more when I’m also regularly creating.

Perhaps you’ve never thought about your personal input/output ratio before. And maybe you’ll never think about it again after you finish this article. But it’s also possible that once this concept is in your head, it’ll never leave. Every time you flip on the TV or navigate to YouTube you’ll feel that ratio getting worse, and then you’ll have no choice but to start a newsletter of your very own.