Leader, Lead Thyself

On loving the Substack algorithm. (Narrator: He doesn't.)

Okay, is this one of those middle-school essays about how hard it is to write an essay? No.

I mean…not really.¹

This isn’t writing about writing. Or writing about writer's block. Or writing about procrastinating to write. I like writing! I do it regularly. I feel like I’m slowly getting better at it (getting better at the practice of writing, that is — output quality is up for debate); I intend to keep doing it.

No, instead this is about all the other work around the writing that a project like Ars Pandemonium demands. And much more importantly, my stubborn resistance to doing it.

I once had a coworker who was reluctantly coerced into a temporary management role. This person was specifically disinterested in management, but stepped up when the team needed them. I said, “well, at least you got to learn a bunch of new stuff.” To which they replied, “yeah, I now know a bunch of things I had no interest in knowing, and would rather forget. Lucky me.”

It wasn’t quite as petulant as that makes it sound — and anyway, I understood the sentiment.

On the one hand, I’d love to believe that all learning is good, that the opportunity to grow in knowledge, skill, or expertise is always valuable.

I don’t believe that we have some finite capacity for knowing things, that bringing in something new pushes out something else (well, maybe the capacity is finite, but it’s very large, and I doubt any of us is really close to the limit there). Nor that new learning somehow dilutes existing knowledge. I’d love to think it’s all additive.

On the other hand, I know that isn’t really true. And that’s because the opportunity cost of learning something new can be very high. The time, energy, and intellectual resources spent on the new learning are, by definition, not spent on something else. Our capacity for knowledge may not be finite, but our time and energy sure as hell are.

As a team leader, I have always tried to be mindful of this. To the extent possible, I’ve tried not to force team members into learning things they didn’t want to, or growing in directions they found irrelevant or distasteful. Of course, not everybody can always get everything they want, and sometimes I have had to ask someone to do exactly that.

In those cases, I’ve tried to help contextualize the value for them and the team, make sure to recognize the effort and sacrifice involved, and reciprocate with resources to put them on a track they wanted to be on.

In general, I think I learned to do this pretty well! Far from perfectly, of course, but I think I was at least a little more successful than not. Therefore, I guess I assumed all of this would just flow forward into whatever solo projects I chose to pursue.

Not so much.

So, back to the issue that spurred this introspection in the first place: the maintenance and growth of the Ars Pandemonium Substack.

Improving the ratio of “adding-meaning-and-value-to-the-world” versus “shouting-into-the-void” requires doing more than just leaving a stack of pamphlets on the giveaway table at the record shop, it turns out.

Expanding readership is hard — or in any event, it’s full of things I don’t want/don’t know how to do. As a leader I know what they are. As a contributor, I don’t want to learn them. Since this is truly a one-man-show, that leaves me in an odd state.

It’s not a question of motivation, as such — I love doing this! It’s challenging in an interesting way, and whether it has value for anyone else or not, the very act of doing it is valuable to me. Anything else is gravy.

So why do I care about expanding it? Well, in fact, it isn’t all that important to me, not really…though more gravy is always good.

What’s much more important is this realization that I’ve had: that I know steps to take, and I know how to lead the team (me) to take the steps, but I seem to be terribly ineffective at leading myself.²

Let me be clear: I don’t have specific goals for subscribers or readership. Maybe I should? I’ve been reluctant to set them for any number of reasons. One, obviously, is that this is essentially a vanity project and I don’t particularly feel like risking failure in my own vanity project!

But it’s also that, while writing “professionally” is new to me and something I’m putting a lot of work into, it’s also something that I enjoy and want to do. The learning is worth it. By itself, though, it’s not really going to move the needle if I want to reach more people.³

It seems widely understood that growing a Substack like this involves, in addition to consistent writing, some combination of video content, podcast-style audio content, deep cross-pollination with social media, and active participation with chat, notes, recommendations, re-stacks, shares, and comments.

And, assuming I want to stay on Substack, I might need to add a paid subscription: because Substack only makes money by taking a piece of subscription dues, a channel like mine is hardly worth promoting from their standpoint.

So. Nothing on that list is particularly appealing to me if I think of myself as a contributor. I don’t know how to do any of those things, and am wary of the opportunity cost of trying to learn.

If I think of myself as a leader, all of my approaches of contextualizing and rewarding are…proving ineffective to convince myself the contributor to do them anyway.⁴

I managed to get over the hump of actually publishing stuff, but it took me a while. I created the Ars Pandemonium Substack in November 2022…and it was March 2024 before my first post went up. I’m sure I will get over this hump too. I’m not too worried.

But it does add a truly introspective dimension to my thinking about leadership.

And maybe that’s the takeaway: maybe the first step of this project is not to go learn all those new things. Maybe the first step is to understand better how self-leadership even works.

Some initial research suggests that at least I’m not alone. This article, called “Leading Yourself First,” has a great quote:

“In his book True North, Bill George tells us ‘the hardest person you will ever have to lead is yourself.’”

Well, ain’t that the truth.

In any event, all of this Substack stuff is very specific to my situation right now, but I suspect the underlying dynamics generalize pretty widely. Have you faced this kind of situation? What did you do?

1. I know whereof I speak. I once wrote what was supposed to be an essay about Wordsworth’s “Lines Composed a Few Miles above Tintern Abbey.” But instead I wrote a piece that exactly aped the structure and form of that poem, but was called something like “Lines Composed a Few Inches above a Computer Screen” or whatever, about the brave student who had procrastinated on his assignment and now faced an unforgiving blinking cursor. I thought it was very clever. The teacher, predictably, disagreed.

2. Or maybe I’m ineffective at following myself…look, this can all get really meta if we let it; hopefully the point is taken.

3. Well, maybe it would be enough if the writing and/or subject matter was more compelling. I know this stuff will never be more than niche — and my ability to write is what it is — but I think there’s more reach to be had. I’m not unhappy with where things are, though! If you’re reading, thank you!

4. By the way, welcome to my brain. It’s an exhausting place to be.