A small, plain envelope showed up in the mail for me yesterday. I didn’t recognize the handwriting, and there was no return name, just a return address in Portland, OR.

My first thought, of course, was “is this some ex? Who have I dated in Portland…”

It was not my love life’s confusing past rearing its head. It was a letter from the Letter Monster.

A while back I was in a characteristic internet rabbit hole. So surprising…

I’m reading articles, chasing stories, and somehow I stumbled upon a project where you submit your name & address, answer 3 questions about what’s on your mind and this person would send you a letter.

I signed up.

Now, I wish I could share the link with you because this is the cool shit on the internet I live for. In true through the looking glass fashion…. I can’t find the website anymore. Anywhere. I’ve googled every keyword combo I can think of and the Letter Monster remains elusive. So if you really want to try it yourself, sorry. LMK, I’ll write you one instead.

Now, this brilliant Letter Monster had some great advice for me. One of the questions they asked in the submission form was about something that’s tough. Naturally, like most days, I had imposter syndrome on the brain and asked about ways to push past that and write daily.

Guess I got in the Letter Monsters head. Because like most writers I’ve met, pretty much ever, they shared that they too find writing marvelous and terrifying and intimidating. Period.

The Letter Monster has been writing letters to strangers for 2 months now, and it doesn’t really get any easier. What does change is how you write. You get better.

Plus, in a way, it does get easier. You learn to put the resistance in the backseat. It’s inevitable that they’re along for the ride, but that doesn’t mean they get to ride shotgun, pick the radio stations, or get into your snacks. They can come along, but the resistance doesn’t get to call the shots.

BTW, the resistance as a personified asshole that makes writing and creative endeavors harder is from Steven Pressfield’s “War of Art”. If you don’t know it, read it, it’s life-changing

The biggest suggestion? Make writing a practice, or a habit…and because the Letter Monster said they “thrash against” this idea of building a practice too I know they’re my people. It’s hard to get momentum and hold it.

Once it’s normal, this practice of yours, you’ll spend less time worrying about getting to the page, and more time filling it.

These are the lessons I’ve learned from my heroes. The Godins, Pressfields, and Solnits of the world. They set quite an example for showing up every day and dancing with the resistance.

So I leave you with some final Letter Monster wisdom:

“It’s intimidating to have talented heroes sometimes, to admit to your ambition to be like them, to find the confidence and belief in your own ability. I heard a metaphor about your goals being a lighthouse once. The ocean is big, and where you end up may be wildly different than what you imagined five or ten or fifty years ago. But having a lighthouse, off in the distance, to aim for at least makes sure all of the work you put in is going in the same direction. You’ll get somewhere.”

Letter Monster, April 2020

It’s interactions like these that make me love the connections that are possible online. Getting letters from strangers that you can tell are your people. And maybe that’s the trick of it. The most meaningful interactions from the internet are the ones that trickle out of the screens and into the tangible world, on paper or in person.

Let us never forget that a tool for connection is just that, a tool, and not our entire reality.


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