Non-Obvious Stuff I've Learned from Writing 71 Issues of My Newsletter

By Lyle McKeany

Here are eight things I learned from writing the first 71 issues of my newsletter.

1.

Self-imposed deadlines work better than I expected.

When I first started thinking about writing this newsletter, I knew I wanted to publish it weekly. I had published plenty of posts in the past, but they had all been sporadic. If I was going to call myself a writer, I knew I needed to show up consistently and do the work.

I not only committed to a specific publishing day, but I also picked an exact publishing time—8:08am PT. The time wasn’t well-thought-out or anything like that—when I was scheduling my first post, I saw I could select a time down to the minute and 8:08 immediately popped in my head. I like it because it’s a subtle nod to the iconic 808 kick drum sound found in countless songs.

The specific time has also had this unexpected side effect of making the publishing time more memorable for readers.

2.

Universality is in the specifics.

In writing communities I’ve joined, such as Foster, I quickly became known for the vulnerability in my writing. One counterintuitive thing I’ve noticed is the more specific I get with my stories, the more they move and resonate with readers.

I wrote about visiting the doctor who saved my daughter’s life and a writer friend told me months later that it’s her favorite piece of mine—and she doesn’t even have kids.

I wrote about my propensity to pass out easily and received multiple comments thanking me for writing about it.

I wrote about my struggle with self-harm and received numerous email replies from people who felt less alone after reading it.

It’s sometimes hard to write about—and essentially re-live—the more difficult moments of my life. But knowing that my words can have a profound impact on even just one reader makes it worthwhile.

3.

Writing isn’t a solitary endeavor.

When you picture a writer, you probably think of someone sitting at a desk, pen to paper, alone with their thoughts. In my case, it’s more like someone sitting on the couch, laptop resting atop a blanket on my actual lap, trying to type while avoiding the myriad distractions available at my fingertips.

But I don’t think of writing as something I only do when I’m alone. I write about real-life events, many of which involve my family. Thinking and writing about these events makes me feel closer to my family. I often read drafts of my pieces aloud to my wife Allison to get her feedback.

Beyond the writing itself, getting editing help and becoming friends with other writers and creative people has leveled up my writing and kept me motivated to keep producing my art.

Not to mention, all of you—my audience. When you click on the heart button on a post you like, leave a thoughtful comment, or reply via email, I feel your love.

4.

It’s too easy to fall into the comparison game trap.

No matter what level you’re at, there’s always another writer who’s further along or better than you. It can be demoralizing to read another writer’s incredible work or to see their audience growth outpacing yours, and then turn to an unfinished draft you’ve been stuck on.

I’ve had moments on Zoom calls when I realized I was that writer for someone else and it struck me that we’re all just people trying to express ourselves. It’s tragic that we play the comparison game so much. It holds too many people back from creating at all. Think of all the amazing art that’s stuck in people’s heads because they’re too afraid to put it out there.

5.

Writing publicly can open up opportunities beyond writing.

This is partially tied to finding community as I wrote in #3 above, but it’s slightly different. By showing up consistently and producing good writing, it leaves the impression that I’m someone who might be a thoughtful person who could quite possibly have my shit together. (that last point is debatable).

I met Nick deWilde about eight years ago as part of a program called Tradecraft where I was kickstarting my career move into tech. We then saw each other occasionally over the intervening years and followed each other on Twitter. Then back in February 2019, he launched his own newsletter, The Jungle Gym. I immediately subscribed and followed along as he steadily grew his audience.

In the summer of 2020, when I was considering writing this newsletter, he was among the first people I reached out to. He then became one of my first subscribers and has been an encouraging supporter ever since.

Fast forward to December 2021, he and some friends were launching a web3 project called Invisible College and he thought of me because I had been writing about my descent into the crypto rabbit hole. He had also observed me in writing communities and saw how active and engaged I was, so it was a natural fit for me to lead the community at Invisible College. It’s still early days, but the project has a ton of potential and I’m having a blast.

6.

Writing about something doesn’t mean I’ll stick with it forever.

I don’t do my mini-workouts before I write at night as often as I should. And I don’t write my 200 crappy words every single night either, even though I discovered that writing in lowercase can help unlock my writing.

Writing can help me process what I’ve done wrong in my relationship in the past, but I’m still bound to do it again in the future.

The good news is that these failings always create more writing material.

7.

I can’t really write with music on.

That is unless it has no lyrics or it’s something I already know fairly well. I guess hearing words while trying to write words doesn’t work for me.

As a result, I often listen to stuff like the Mr. Robot soundtracks, movie scores by Hans Zimmer, and artists like Woodkid, Sevdaliza, Radiohead, Burial, James Blake, Son Lux, Björk, LORN, TOOL, DJ Shadow, and a bunch of others I’m forgetting right now.

8.

Building an audience isn’t all that important to me anymore.

Don’t get me wrong, I’m incredibly thankful to all of you reading this piece right now.

When I first started, I had dreams of building a massive audience. I was going to write a bestselling memoir and enjoy all the adulation and accolades that come with it. The more I explored that path, the less excited I became by it. Yet I’m still drawn to the art of writing personal stories. I’m also having more fun making friends here and on Twitter without the stress of trying to grow my subscriber base and follower count.

Most writers who build large audiences quickly are writing for a particular niche. Like, I could’ve set out to write a newsletter about web3 and I can almost guarantee I’d have a way larger audience than I do now. Instead, I’d much rather have the freedom to write whatever the hell I want each week, like taking my readers on a journey from writing about my father’s passing one week, to writing about couches the next.


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