What I've learned from writing this thing for exactly 3 years

Sep 16, 2023

As of today, I’ve been publishing on Substack for exactly three years now. In that time, I’ve learned some valuable lessons about how to publish consistently and (sometimes) write my best work.

Let’s get right into them:

1.

You’d think with three years of posts under my belt I’d be able to get into the writing flow more quickly by now.

Nope.

It’s often a struggle not only to do the writing itself but to get myself to actually sit down, open my laptop, and start writing.

As I’m writing these words, it’s Wednesday afternoon and I’m sitting here on Zoom quietly writing. I host what we at Foster call Authoring Circles twice per week. In the sessions, I start them off by grounding everyone into the space and helping them set whatever other priorities or stresses aside so they can creatively explore their writing for roughly an hour. It’s a foundational practice in the Foster collective and one that I’ve found to be invaluable.

The problem is, I’ve been in a creative slump lately.

I hosted a session on Monday and mostly stared at a draft I’ve been wrestling with for weeks. After about 15 minutes of starting and stopping and hemming and hawing, I ended up getting some work done instead, which is decidedly antithetical to the whole premise of Authoring Circles.

In the past, I’ve written about how important it is to write daily. I do write something every day—emails, Slack messages, journal entries, text messages. It’s just that most of that writing doesn’t end up getting published here.

Yet I’ve been doing this long enough and consistently enough that I have faith that I’ll come up with some sort of topic to tackle or story to tell eventually. My mind is attuned to scanning my surroundings, psyche, and emotions for writing fodder way more than it was prior to starting this newsletter. Or, as I wrote about in an advice column previously, I’m trained to observe always and write often.

2.

Since I publish something original nearly every week, you’d think that my well of writing ideas would be overflowing.

But ideas are fleeting. Unless you capture them somewhere, they tend to leave almost as quickly as they come. This is why I always say that the best notetaking device you can use is whatever’s closest to you when inspiration strikes. For me, it’s usually the Apple Notes app where I have a gigantic bullet-point list of random thoughts, half-formed concepts for essays, title ideas, etcetera.

Here are a few examples I plucked from my list to illustrate the range of stuff I toss in there:

Isn’t failure just a part of life? Why do we hang onto these things so much when we know they’re going to happen anyway?
Tell a story that occurs while getting my teeth cleaned. So it’s punctuated by parts where I need to spit or whatever
“You forget what you want to remember and you remember what you want to forget.” – The Road, Cormac McCarthy
How Sara said a show wasn’t super violent but then said someone gets murdered in it
Am I weird enough?
Title idea: You’re more resilient than you realize

It doesn’t matter what you use to capture these potential future gems, just snag them before they dissipate into the ether.

But there’s another problem with ideas: they become stale. And to complicate matters, it’s as if they have those “best if used by” dates stamped on them in invisible ink. You never know exactly when they’ll go from feeling like crispy tortilla chips straight out of a freshly opened bag to feeling like tough triangles that taste like cardboard.

Here’s a case in point. The draft that I mentioned above. The one I’ve been struggling with. It came from the title idea “You’re more resilient than you realize.”

At first, I was excited about it and I jotted down a couple of sub-bullet-points:

How we can all adjust to our circumstances and how eventually they become sort of boring and rote, yet when you zoom out for a sec you think how crazy it is that they’re normal now
Obviously, talk about our life with Em, but also talk about the pandemic and even our crazy day-to-day lately where we’re driving all over the place every day

Okay, cool, I thought, there are some stories I can tell in there.

And so I started riffing on them. But they all kinda led me to nowhere all that interesting. I tried following my curiosity more and free-writing on the topic for a bit. Still, I was feeling stuck.

Then I remembered reading a quirky memoir/advice book by Augusten Burroughs earlier this year. It’s called This is How and has this absolutely chaotic subtitle: Proven Aid in Overcoming Shyness, Molestation, Fatness, Spinsterhood, Grief, Disease, Lushery, Decrepitude & More. For Young and Old Alike. I recalled reading a chapter that was somehow related to resiliency. I did a little digging and found this banger of a quote, which I’m just going to share now, but I reserve the right to share it again later because I really like it, okay?

“Even when we lose an arm or a leg, there's not less of us but more. Human experience weighs more than human tissue.”

I love that quote. It speaks to my experience as a writer. And so I started thinking of ideas and related stories from my life around that idea. But that’s when I quickly realized that the quote is not so much about our ability to be resilient in the face of adversity, it’s more about how human experience shapes who we are.

At that point, it was clear that I was forcing the issue and trying to massage and twist the material to work with the title idea I liked. But the idea had gone stale. It started to feel more like a chore to—attempt to—write about it. And so I let it go for the time being. Maybe it was meant for some other writer to grapple with in their own unique way instead. Ideas have a way of doing that.

As Rick Rubin wrote in his book (which I highly recommend for anyone doing creative work) The Creative Act:

“If you have an idea you’re excited about and you don’t bring it to life, it’s not uncommon for the idea to find its voice through another maker. This isn’t because the other artist stole your idea, but because the idea’s time has come.”

3.

You’d think that readers would get annoyed if you republish a piece.

But nobody cares.

I’ve never had a single reader complain when I’ve done it. Actually, I’ve experienced quite the opposite.

When I republished my fictional short story You’re gonna wanna see this earlier this month, I even received a few comments from subscribers who loved rereading it a second time.

Assuming your audience is growing steadily, when a fair amount of time has passed from the day you originally published a piece, you’ll have a whole new swath of subscribers who’ve never read it before anyway.

Sure, maybe some readers unsubscribe. But as my friend

Alex Dobrenko`

succinctly wrote about publishing re-runs (as he calls them), “Any of your readers that matter won't care and anyone that cares doesn't matter.” Unsubscribes are part of putting your work out there for public consumption. Get used to it.

Bonus tip: If you write on Substack or a similar type of platform, turn off notification emails for when people unsubscribe. Seeing them just makes you feel like crap, especially if the unsubscriber is someone you know personally. It’s just not worth it—or all that useful—to see them in real-time. Do yourself a favor and nix them ASAP.

4.

Exactly three years after I published my first post here, which was literally titled I’m a Writer, I still struggle to say I’m a writer.

I’ll meet someone for the first time and when they inevitably ask me what I do for work, I sort of mumble that I write some stuff on the internet and I edit things too and do some creative coaching on the side, but also mostly work for Foster these days. Ugh, awkward. I feel like after three years of doing this thing and writing who knows how many thousands of words at this point, I should be able to own that I’m a writer. I should be proud of it. And I should definitively say it, just like I wrote it in that inaugural post three years ago.

Perhaps the problem is that I don’t make my primary living as a writer. I do have some paid subscribers (thank you!), but at this point, they basically help support my golf habit more than anything else. Which, ironically enough, is where I tend to meet new people and routinely fumble my way through describing my vocation.

Part of the hang-up, for me at least, is that I can’t point people to a book I’ve written. Y’know, something the average person could physically hold in their hands and easily understand as writing. And something that seems more serious and worthy of the capital W, Writer, designation than a newsletter or blog or whatever you want to call this endeavor. It’s funny how writing on the internet has been a thing for a long time now, but so few of us actually do it that it still feels novel and weird to most people.

5.

Okay, last one. For me, right now as I’m typing this piece, this is the most important lesson on the list.

To keep a newsletter going week in and week out, every once in a while you just need to write a milestone post like this one.

And that’s okay.

By the way, at Foster, we just announced Season 4, our next month-long, uhhh, thing which we describe as “somewhere between a course, bootcamp, summer camp, accelerator, and hogwarts, and yet, not quite any of these things.”

If you’re a writer who wants to dig deeper into your lived experience and write stuff that’s more true and alive, Season 4 is right up your alley.

Just Enough to Get Me in Trouble

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