Solving the Cave Riddle

Follow-up to I am Currently Failing - Part II

So, there I was in an office parking lot holding the golden leaf: the answer to The Cave Riddle and my own real-life problem.

To explain the golden leaf, I have to take you back a little ways first.

In my last post, I mentioned that I haven’t worked in an office in 15 years. At the last company I worked at, my peers were mostly former management consultants. They thought in very structured ways and were methodical and linear. They loved boxes and rectangles. Flowcharts. Project plans. Spreadsheets. If it had objects with four sides, they loved it.

I… on the other hand… I am not that way.

If they and I were each objects you might find on a desk, while they’d be calculators, I’d be a Magic 8 Ball.

And if we each saw a Magic 8 Ball on a desk, they’d point out that there is a flat 5% chance of any specific answer appearing; and I’d be like “SO, YOU JUST NEVER KNOW. THAT’S THE FUN, RIGHT!”

Management consultants are good at solving problems where they can impose structure and process which governs how things are done and will work.

I, on the other hand, am good at solving problems where that kind of structure and order isn’t the answer… and that insight is what plucked the golden leaf from the God-tree of Writing and sent it dancing on the wind.

When it landed in my hands, it bestowed a glorious clarity: the thing that made starting this Substack so joyful – so truly, truly joyful and fulfilling and happy – was that it was the first time in my life – truly ever in my life – when what I did for a living fit with who I am and how I am and how I work.

I have ADHD. I have talked about that often. One thing people with ADHD – or people with any difference which puts them outside the mainstream, really – get very used to is the fact that the world is not designed for us. It isn’t even really designed to accommodate us.

Instead, it is designed to best serve a population we don’t fit into. At best, it can be made to flex a little bit so as to not entirely exclude us; but it is not designed for us… and it can’t really even be made to fit us.

That reality is just so entirely central to the entirety of our lived experiences, I suspect most people with differences couldn’t even tell you what a world designed for them would like without having to think about it… because it isn’t something they have ever entertained as something that could exist.

By flinging myself off a cliff into being a writer, without knowing it or realizing it, I created an opportunity. An empty lot awaiting an edifice. What would be built upon it was the puzzle to solve; and with the freedom of an empty lot with its absence of structure and constraint, that puzzle was an unstructured problem… and, shit, those are my goddamned forte. Those are the kind I used to run rings around the ex-McKinsey guys on.

And, yet, I neither saw it that way nor capitalized on it.

Instead, I subconsciously defaulted to seeing it like most everything in the world – as inherently structured. In the back of my mind, I filed away what I saw from looking at other people’s Substacks. The structural norms. The layouts and adherence to a narrow set of topics and publishing schedules and methodical regularity. Structure. I just filed away in my mind that there was a structure to how to do this thing and a lot of people were already following it.

Initially, that had no impact because at the outset, I gave myself permission to just write without any restriction of any kind. Not subject or length or frequency. No parameters. Just write, bro.

I did that because this whole crazy leap into writing was basically like abruptly announcing “I AM A RESTAURATEUR NOW AND MY RESTAURANT IS OPEN.” despite having never worked in one and not knowing how to cook. I needed to learn how to both cook and run a restaurant. That latitude to just write was permission to go focus on the cooking first: Whip up dishes; make a mess of the kitchen; and learn from it.

My loose plan was to let myself just cook for the first six months and then pivot to running the restaurant; and I thought the experience would better prepare me to do that.

The thing I never thought about was what kind of restaurant I wanted to run - or if I even wanted to run a restaurant like everyone else per se.

Then, as I started to come under pressure these past couple months, without realizing it, I processed my flattening trajectory the way I have been conditioned to process literally anything at all where there is a perceived grade and mine has slipped:

I wasn’t applying myself. I wasn’t working hard enough. I wasn’t living up to my potential. I wasn’t succeeding in the system all of my peers and I work in. Basically, I was a kid with a goofy haircut and a middle part getting a C in AP European History again while other kids who weren’t smarter than me were getting A’s.

With that subconscious default to ‘structured thinking’ and ‘struggling with structure,’ I never even stopped to think about whether that structure existed or needed to or could be changed.

And the answer is: no, it doesn’t actually exist or need to and I am not beholden to it.

The irony here - and this is truly an irony, which, if you had worked closely with me when I was a strategist, you would fully appreciate – is that MY ACTUAL CHALLENGE HERE is the kind I am really good at solving.

The challenge here isn’t just about me. There’s a ‘me’, a ‘you’, and a ‘we’.

To solve it, I need a solution which serves all three.

It has to make me happy and be within my capabilities; it has to result in a Substack feed you enjoy and feel is good value; and it has to enable me to expand our little circle from us to a bigger we.

First, the ‘me’ part: what makes me happy and works for me…

My brain is essentially a 3-year old golden retriever.

Not a puppy. Not an older golden which has kind of mellowed out after those, oof, high-energy first few years. A 3-year old golden. My brain needs exercise. It needs to be allowed to run off the leash. It needs to be taken for walks. It’s okay with some structure and confinement but not rigid cloistering. Give it enough exercise and stimulation, it does fine with some time in the house. Never let it out though, it’s going to tear the absolute shit out of the sofa.

That is my brain. That is how my brain works. It has always worked that way. It will never not work that way.

And, at this point in my life, I don’t want it to…

There are some pretty amazing things about having a ‘golden brain’… which, granted, is short for ‘golden retriever brain’ but, ya have to admit, ‘golden brain’ has some pretty sexy brand panache. Still, if heard out of context, it would sound super obnoxious, so hereafter, I am going to refer to it as just ‘GRB’ – golden retriever brain.

To serve me, a solution has to serve my GRB. Not engineer around it. Not accommodate its limitations. Serve it well and actually lean in on what it’s good at where it thrives.

Now, to serve ‘you’ as readers, I need to remedy things that haven’t served you well; and I need to go beyond that and take this feed higher to serve you even better.

Serving the ‘you’ part requires some structure. The art is in building it in so it works for both of us.

In my little Sunday parking lot walk, I came up with a framework that I think does that.

It blends some flexibility for me with some structure for you; and it affords me some latitude to still let my GBR off the leash sometimes - but not all the time and not for miles and miles like I have.

The changes I have in mind to take this from Hoarse Whisperings 1.0 to 2.0.

Hoarse Whisperings 1.0

-         Whatever Mike wanted to write about published whenever he published it

Improvements in Hoarse Whisperings 2.0

• Content length:

  • A better mix of lengths skewed toward shorter reads.

    • Targeting a mix which breaks down to 3-2-1 or 4-2-1: Three or four short pieces and two medium-length pieces for every long one.

• Publishing schedule:

  • Akin to The NYT Crossword Puzzle model: (Easiest on Monday; progressively harder over the week; Sundays are a whole ‘nother Magilla.)

  • Now, apply that idea to the 3-2-1 or 4-2-1 content mix above

    • Shorter pieces heavied up early in the week. Medium ones generally later in the week. Longer ones held for weekends.

• Content organization:

  • Introduction of some new offerings:

    • Organized around their content

      • Ongoing series

      • Recurrent topics and themes

    • Organized around their style length and style

      • Specifically, pieces meant to be snacks or lighter meals spanning an array of topics

The above is “flexibly structured”. It gives me room for the things I need, am capable of, and want… and I think it fits with what y’all have asked for and suggested… and I think it paves the way toward a newsletter which is a good read, a good value, and a good experience.

While reining things in somewhat, it doesn’t hem me into having to publish X pieces a week or post specifically on this day or that; but it creates some order around this thing

I think it works for the two R’s… The Reader and The Retriever. You and my GRB.

Tomorrow, I’ll tell you more about the new offerings I have in mind (under the “Content organization” bullet above). I like them. I’m excited about them; and I think they’ll be enjoyable, hopefully, for both of us.

Last thing for you before closing… About that Cave Riddle…

In my dream, ironically, I never actually tried to squeeze through the opening. I just accepted that it was too small… That’s the thing about constraints. Sometimes, we too easily accept that they exist and that we can only work within them. I invented the cave. I can simply decide the rock was sandstone and then shape it into whatever I want. So, I’m turn it into a writing cave. I might add some big carriage doors… add a space heater and a dorm fridge… throw in an old sofa and some old rugs. A writing cave that is an actual cave. I mean… that would be cool. Unless there were bats.

Anyway, y’all are invited over.