The Anatomy of Failure [Trenchant Edges]
Hello again!
This is the Trenchant Edges, a newsletter about whatever I can get myself to write.
This is going to be one of those inward facing self reflection posts so if you’re not up for that skip it.
Leave a like on substack if you’re especially kind!
Basically, the thing that doesn’t work here is also the thing that does. And they’re both uhh who I am as a person.
My original plan for TE was to have something pretty narrowly focused and clearly defined and while that’s been laughable for literally the entire time I’m tired of having so many open loops and constantly opening more loops.
Which, uh, doesn’t seem likely to change.
This post is me trying to do two things:
Getting enough clarity about how this process works that I can do something different.
Publishing to clear out my anxiety/guilt about not having finished something.
Naval Gazing into the Abyss
This newsletter was started on June 20th 2020. As I write this it’s March 16th 2026.
That’s 295 weeks of “doing” Trenchant Edges.
I’ve half abandoned it a pile of times since then. We’ve had about 220 posts since then, which is quite a lot. Even if I’d originally planned doing something a bit more regular, smaller, and weekly.
I’ve tried a pile of different structures here and none of them have improved things.
Now that’s tricky to assess because I spent the first 5 years of this newsletter dealing with crippling back pain and most of the last year recovering from it.
Can’t be mad at myself for that.
What I can be a little mad about is how often I’ve skimped on editing because I felt too much pressure to be done and just said fuck it. I know I’m capable of doing excellent writing with the right amount of polish.
Now, this pressure doesn’t really come from anyone else. My sense is that the people I’m writing for don’t give a shit as long as it’s good.
The pressure comes from a mix of my creative ambitions and the needs of this thing as a business.
Oh and a pile of mental illness.
Shocker, I know.
So I’m a Little Insane
About 20 years ago I was suicidal and a senior in high school. As a self-motivated, traumatized child with both ADHD and Autism, US public schools were a profoundly hostile place for me.
Because of the profound ignorance of neurodivergence at the time, my conditions masked each-other. Too ADHD to be autistic, too autistic to have ADHD. Mostly I seemed like a bright but hot tempted child who didn’t respect any authority.
Which to be fair was entirely correct.
But nobody understood why, myself least of all.
Even then my emotions tended to be a bit extreme: Elation and despair. Rage and peace. Love and hate.
I feel without shock absorption.
As an adult I kind of prefer it this way. I’m rarely bored and it’s not that much effort to manage most of the time.
Practicing meditation in my 20s helped me actually get good at this for the first time. But mechanically, it’s still an effort of will to control which really started to get janky once my physical energy was spent enduring pain.
So, to that mess which includes Rejection Sensitive Dysphoria and Pathological Demand Avoidance, got a bonus difficulty of managing my herniated disc.
I realize that’s all a bit melodramatic but it doesn’t really feel that way. This is just who I am and who I’ve been.
The difficulty has been figuring out how to live with all this.
See, I have this reoccurring fantasy built /on the shocking success I had recovering from trauma in my 20s that one day I’ll be fundamentally different. I do not believe this is the case.
My challenges today, mediated by how much I recover from the back injury, will probably be my challenges 50 years from now. You know, plus whatever new bullshit I get from aging and all the history that keeps happening.
And the slow improvement I’ve seen in that over the years has me pretty comfortable with that fate.
So let’s get into the other side of this.
The Anatomy of my Failures
Here’s the thing: I like being good a stuff. Skills are a pleasure to have and use.
I like writing and LOVE realizing I’ve written something really good.
It’s hard work. But I enjoy it. Until I don’t, lol.
The hardest thing for me to do in any context is start something. Once I’m moving I’m usually fine. But getting going is… tricky.
There’s a bunch of ADHD crap about dopamine and focus here but we’re mostly going to ignore that. Point is, at any point there’s a bunch of stuff I know I need to do and I need something to hook into the task to get me going.
It’s a lot easier if I’m working for someone else.
Which is crazymaking. Like, I’m a pretty good manager but my nervous system will argue with me if I want to manage myself? What bullshit is that?
This makes long term research projects like the ones I want to do here really hard because those require me to skillfully get myself to do the right shit and not be distracted over weeks or months.
This is… difficult.
And the output of this newsletter is exactly what you might expect: I come up with new ideas to chase but never really get as deep into them as I want to.
Occasionally I’ll get a couple good weeks in.
But overall it doesn’t really work even when I’m working.
Which leads me to chasing my own tail
So, let’s walk through this and ignore my awful penmanship.
Idea to Research Something
The Dunning-Kruger Slide: Oh fuck there’s so much more I need to know to even be able to tell if my argument means anything.
Try to Catch up
Panic on realizing it’s almost been a month since I last published.
Fuck, I need an idea I can do without researching anything.
Repeat to #1
That’s how you get this newsletter.
And while it hasn’t created what I want, it has created a lot of good stuff. There are some real bangers here.
But that runs into another issue.
The Business
This newsletter has been in a weird place for a long time. I have enough people paying that I don’t want to give it up but not so much that I can actually afford to do this for even a major part of my income.
I live real cheap so I can get away with this. But that’s now out of the question because I own a car and those bills are going to add up quick.
And there’s just a flurry of shit that goes with this. Doing stuff to make money takes time and energy I can’t spend on research. And most of the things I do for money are too expensive in time and energy to have much left over.
So the next round of trying things is doing some gig-tier medical courier shit and hoping that’s cheap enough I can work effectively here while trying to figure out how to sustainably expand traffic.
Fuck if I know if any of that will work out.
What Now?
That’s the long and short of it. I could get into a ton more detail but I don’t think that’s useful.
I haven’t been idle in the last month, but we’ll see how long it takes to turn the crap I’ve written into something good actually. The point of this post is to break the feeling bad about myself part of the cycle so I can get back to the work.
Anyway, I’m tired from this and going to go take a walk.
See y’all soon.
-S
Would appreciate any of the thoughtful comments y’all usually have.