One Hundred Posts in Retrospect

I recently wrote my one hundredth post here on Substack. This milestone crept up on me a little bit, but I suppose when you write one newsletter a week, math takes care of the rest.

That’s the beauty of maintaining a routine.

Time passes whether you’re paying attention to it or not.

Suddenly you look up and find you’ve got a decent amount of work under your belt.

Routine comes easy to me. Perhaps this is why the milestone doesn’t feel so momentous. I didn’t have to grind to get to one hundred newsletters. All I did was turn up and write, just like I do every morning.

Before I err too much into humble-brag territory here. I should point out how being wired this way isn’t always a blessing.

As I’ve mentioned before, the quote “never mistake motion for action” has been stamped on my laptop background for the last five years.

For a reason.

The pitfalls

It’s easy for anyone to fall into auto-pilot mode. But I think even more so for someone like me. I’m more susceptible to digging in and doing the thing without scrutinizing what element of the craft I’m trying to improve on that particular day.

The amount of joy I get from applying the skills I’ve already internalized, puts me at risk of going back to the well and revisiting the tried and true, simply for the kick I get out of it; neglecting the deliberate practice required to add new elements and fill out my skillset.

This is the quality that makes me obsessively pick up a guitar whenever I’m in a room with one, yet, keeps me from sitting down for thirty minutes and learning a new song.

It’s the quality that allows me to go into the gym and handily beat people with techniques that are downloaded to my muscle memory. Yet when quizzed on the intricacies of that very technique, I’ll barely be able to remember the position let alone name it for you.

There is something to be said for this playful approach, the flow state if you want to call it that, but it has a ceiling. It only works on people who aren’t as skilled as you. When you meet your match, you need structured technique and methodology to fall back on.

It’s harder to see that with subjective pursuits like writing, but the principle holds:

Unless you’re engaging in a creative pursuit solely for the sake of itself, you need to hit a baseline of mastery before you can rely on that flow-state to get you across the line at the upper levels.

The risk is finding yourself in a place where you’re repackaging and rolling out the same old tired work. Technically “new” to you, but of a recognizable kind. Or perhaps even stepping into new territory, but doing so without the awareness to realize you’ve done so, and therefore, robbing yourself of the ability to expand and build on that development this playful approach has delivered to you.

Sure you’re prolific in one way, but if you’re not doing it with a trajectory in mind, you may as well jump on a hamster wheel.

All of which begs the question: After writing an average of four newsletters a month since November 2022, have I improved in any noticeable way?

Letting go

One thing I’ve definitely improved on is being so guarded about my work. Recently at the office, it got unearthed that I’ve been writing for a while. After about nine seconds and two key strokes, my Substack page was on the screen.

My first instinct was mortification. They may as well have been cueing up naked photos there.

Then I saw the story there up on screen, it was my most recent short story “The Scorpion,” (which actually opens with one of the soppiest stretches of dialogue I’ve published to date). My face was bright red and I braced for a wave of shame. But when confronted by the brick and mortar of the words I’d written down. I found I was perfectly fine.

See it’s the idea of someone writing in their free time that contains all the bottled up cringeworthyness. It invokes some wet, overwritten, purple prose or preachy shit.

But I’m not typing up slam poetry here.

Sure I’m definitely guilty of overwriting more regularly than I’d like to admit. But there’s a point to everything I write. I stand behind every word I put on the page—even if that just means, I stand by it as a representation of my thoughts at a given point in time.

Learning my place

When I started The Sudden Walk, I committed to writing one newsletter per week. I began with a backlog of pre-written short stories to get my first three months or so covered, but it didn’t take me long to catch up.

My original plan was to post fiction only. There’s a Ray Bradbury (Fahrenheit 49) video floating around on youtube. Here. where he advises new authors to delay writing that big novel right out of the gate. Instead, begin with short stories. Aim for one story a week and by the end of that year, you’ll have finished fifty two stories containing a multitude of lessons it may take decades to learn if you’re tinkering away on a novel alone.

I half followed this advice—though I was also working on the novel at the same time—so in practice it was closer to a few days per week spent on each of these stories.

As one might predict, shortly after I began my attempts to write at this clip, I started to notice the quality dipping, repetition started to creep in and I published a few stories here that felt half baked.

It’s one thing writing the fifty-two stories that no one will ever see, but publishing them with your name attached is another.

At this point I wasn’t sure what I wanted the page to be, but I knew I didn’t want it to be another fast churn, low quality pulp posting page.

So here I introduced my first non-fiction post. Which was a bit of a leap, because there’s a jump in vulnerability going from writing characters to drawing parallels with real life—my life—and I suddenly had to navigate the question of how much personal stuff to layer in. How much do I want people to know/how much interest do people even have in knowing?

I settled on keeping the topic matter writing related for the most part, so at least there was a throughline across the different posts.

This was a half solution. It allowed me to keep the fiction to a fortnightly basis which was a better turnaround for me.

But then I started getting a bit of imposter syndrome as far as the writing posts were concerned. Was this a technique page? If that was the case, why would anyone come to me rather than one of the many established or famous author’s here on Substack?

Who am I after all?

When I genuinely considered this question it clicked.

I’m an aspiring writer, trying to get a foot in the door and have my work published.

That’s what I bring to the table.

That’s the thing the established authors can’t offer. Because they’ve already done it. There’s no journey left for them. Anything they come out with in that vein is in retrospect, nostalgia.

The Sudden Walk is an in-the-moment newsletter.

This was a solid revelation, because it took a lot of the pressure off the need to be an expert and allowed me to be a bit more honest about my approach. I’m just tackling this pursuit as best I can with the info I’ve been able to gather about how it all works. It’s not a “how to do,” it’s a “this is how I’m trying to do it.”

Take what you want from it. Capitalize on my mistakes as much as my advice.

That’s the angle.

Making friends with the reader

Early on I was caught up in the idea of giving my stories layers and depth.

I still aim to do that now.
But with less smoke smog.

My initial swings at infusing depth involved burying plot lines. I got into the habit of planting too subtle winks towards what a story was really about. Trying to outsmart the reader.

After one too many, “I don’t get it?” reactions, I came to terms with the fact that it’s much better to let the reader in on the punchline.

Make them feel smart, rather than the other way around.

After all, you write a story with the intent to make the reading experience a satisfying one. If your puzzle is so cryptic that it requires an explanation at the end. You’ve missed something.

I’m sure I’m yet to get the dials perfectly balanced on this front, but I’ve made conscious efforts to pull back the subtlety on my short stories lately and have received feedback that they read with more clarity now. So that’s an encouraging sign that I’m on the right track.

Lingering in the editing room

Though this doesn’t exactly harmonize with what I suggested in the last section, during my early stages as a writer, whenever I had a premise for a story, I would try to get it down on the page as quickly as possible—and from there I’d be excited to get feedback as soon as possible. As a result I’d send my new piece out to people prematurely.

Because it was fresh for me, I would always be too close to these new stories. I’d think they were better than they were. I’d think they were closer to the vision in my mind than the reality on the page.

With the help of feedback, good advice and plenty of reading, I made a habit of sitting on work for a while before putting it out there. Letting the initial enthusiasm die down, reading it for what it actually has to offer, and searching for new angles that might expand the themes that have percolated out of the first draft and leverage them for a deeper meaning.

As I write this, I’ve got at least five stories that are over twelve months old which I had considered at one point “finished,” but are now subject to the aforementioned scrutinization process to try to make them better.

Now I will add the caveat that there is a risk of over analyzing. Sometimes simple is better. So I’m conscious not to try this on every story. Only the ones which promise they could do more.

But again this is all subject to my developing eye for story. Something which I’m doing my best to dial in.

Maintaining a Standard

I’ll admit, there have been times since I started The Sudden Walk, where I was tempted to phone it in or worse, just renege on posting a newsletter for a few weeks in a row.

Equally, I’ll acknowledge that some of my articles are better than others. That’s impossible to avoid, but the effort to be original is always there. I’m not trawling for SEO visibility here, I put thought into every post that appears here.

Unlike the penchant for routine I referred to in the opening of this article, this part is not hardwired into me. I owe the pressure to keep up the good work to the people who read these things every week.

While I try not to look at the numbers too much. It is humbling to see people open these things and listen to me talk about esoteric shit that probably has no relevance to a lot of your lives.

There is a quality in this page that keeps me fueled.

They keep me honest.

And as far as my paid subscribers are concerned: It’s not lost on me that there’s a charity element to that. I know most of you. It’s coming from a place of “showing an interest” rather than an “organic interest” necessarily. But it’s all momentum and I’m grateful for that.

When I’m in a position to give back, I will.

But none of it’s taken for granted. I think a lot about how to make all of the time spent here worth it. To make it mean something. One day it will.

So there you have it

I’ve just written a post that is far too long a goes against a lot of the lessons I’ve outlined above.

But I think I’m getting somewhere with this thing all the same.