Reflections on my First Month of Content Calendaring

“Thanks, I hate it!”

Published on February 7, 2024

Table of Contents

Content calendaring: the good, the bad, and the practical

As you might/might not know, one of my New Year’s resolutions is to keep a content calendar for every month of 2024, and do my best to stick to it so I can finally have some content on this blog.

A spreadsheet with dates and corresponding tasks, labeled things like “Boba
Socials - Content boost” or “Personal Socials - Project update”. Tasks are
things like “Announce new streaming schedule” and “Part 2: Legal Structures”.

A screenshot from my content calendar, featuring my content creation schedule for January 2024.

While I had tried and very much failed to keep such calendar before, this year I managed (at least as of January) to push through my past hangups and deliver some Juicy Content™. Without sugarcoating it, this was an emotionally charged journey. There is a lot I don’t yet love about creating content, but I’m happy I took the plunge and somewhat landed on two feet.

With this first month behind me, it’s time to look back at this trial and share a few thoughts on what was good about it, what was less good, and some hard numbers on what the result of it was.

Bonus thoughts: Why I succeeded this year
  1. I got practice: promoting the FujoGuide Kickstarter was an incredible amount of work, the most grueling part of which was maintaining a calendar and writing content every day for a month straight. As usual, at least for me, “swim or sink” is a very efficient, (mostly, with hindsight) “enjoyably stressful” way to learn.
  2. I got schooled: in December, I did a small content trial, and I tried streaming twice a week for a month straight. Unfortunately, I’m sad to report that “you need to publish on a consistent schedule to grow a public” is not a Big Content™ ploy to personally vex me.
  3. I got motivated: tl;dr, I gave myself until August to prove to myself that my ambitious plan can work. Unfortunately, as I realized, people cannot support what they don’t know about–even if telling them about it takes time and energy away from working on the thing itself.

The good

I learned to care about the who and why

As “the poster child for ADHD”, I unwittingly perceive my time (and energy reserves) as vague, nebulous entities with little bearing on reality. While this can be an advantage at times1, this perception of boundless resources can easily keep your wheels spinning in place. It’s known that adding constraints makes broad problems easier to tackle. In the same way, filling limited calendar slots with scheduled articles forced my brain to see to see that there’s a limit to the amount of content I can produce in a month2.

In this case, the limited space on the calendar forced me to ask the question: what does truly matter to people out there? What can I write in these limited slots that will make each of them count? What will resonate with those whose support I seek, and what do the people I work with need to know that only I can tell them? Once you recognize the boundaries of your time, it becomes easier to make choices about how to use it. And while I can’t say I’m good at answering these questions, I’m glad I’m learning to ask them.

This experience also gave me a new appreciation for the practical skills required to create content for a living. People often wear the badge of “bad at socials” with pride, as if it were an immutable characteristic of their being. However, once you see creating content as choosing what’s worth your time and energy, it becomes a trainable skill rooted in empathy. Deliberate, thoughtful content production can pave the way to genuine connection and dialogue. Every article is an excuse to start a conversation with a broader community, and to engage with them through new knowledge or perspectives on topics they care about. Becoming a “content creator” is moving from making content at people to making content for them.

I wrote some useful things and got some good software done

At this stage, my job is to make content. Whether I like it or not, writing useful software or plotting brilliant organization-building plans is secondary to gaining enough support for that useful software and those brilliant organization-building plans to effectively matter. “Build it and they will come” is wishful thinking. Unfortunately, “tell them about it often enough, and they might show up, maybe, one day” just doesn’t have the same ring to it.

Among the things that kept me from making content a priority is that I am (by all reasonable metrics) just too busy for it. However, once I accepted this is my life right now, I was able to, as they3 say, “bait two seme with one uke”. By positioning my content at the intersection of “what’s useful to our goals” and “what supporters outside might care about”, I was able to work on things I felt truly mattered, like putting an ambitious plan into linear words 4, showing beginners they can aspire to more than simple websites 5, or educating people on topics they’re unlikely to seek out on their own.

Similarly, maintaining a streaming schedule allowed me to make progress on the software I need to build while teaching people to build theirs at the same time. Nothing says “what you’re doing makes a difference” like seeing a used-to-be-beginner put together concepts they learned through “listening osmosis”, and realizing they now understand web development at a deeper lever than they ever thought possible. While my challenges in empathizing with beginners as someone who’s been writing software for twenty+ years are a rightfully-recurring joke, building software in public had (and will continue to have) an impact that goes beyond the code itself. 6.

I survived! (somehow)

Aside from the crushing abyss of a blank page to fill (which strict deadlines help me get over), my least favorite part of creating content is the perceived sense of rejection from putting it out there and getting little practical interaction back. This is a struggle for everyone (especially with social media as it exists now), and I hesitate to say I have it worse than others here. It does, however, impacts me more than I wished it did.

What’s helping me get over it, aside from inoculation through repeated practice, is understanding that content production behaves like compound interest7, and “money”–or, in my case, “Patreon support”–is a lagging indicator8 of doing a good job at it.

The monkey in my brain reminding me that the best way to get over the emotional turmoil of producing content is to keep producing more of it.

While some days of publishing still feel better than others (and likely always will), I believe this will improve with time. After all, I can point to many aspects of building communities and leading projects that I can easily juggle now, but that used to be a great source of stress just a few years ago 9.

Regardless of how my feelings about content will evolve, however, what matters is “I survived January 2024”.

One month down, eleven more to go.

The bad

Social media is broken

Proclaiming that “social media is broken” has always been a surefire way to gather accolades for stating the obvious. However, the experience of producing real content made me appreciate it to a whole new level. Years ago, I used to be able to “casually shitpost” my way to engagement; these days, the landscape feels so bleak that my desire to shitpost is nowhere to be found, and getting engagement on more serious content has become an Herculean task.

In part, this is due to the history of the specific community that I’m trying to reach (that is, “transformative fandom”). First, Tumblr’s demise 10 scattered us to more nipple-y social pastures; then, Twitter’s current whatever-that-is delivered the final blow. How can I reach people where they’re at, if “where they’re at” is everywhere and at the same time nowhere? “Casual shitposting” just doesn’t feel as casual when you have to do it across four different socials.

Don’t get me wrong: I’m the first one to say that less people on more platforms is great. However, it’s clear that technology has yet to catch up with the current situation, and it’s harder and harder for people to find community within this scattered and often hostile landscape. When you don’t have a community, it’s harder to feel your interactions with others matter, and the resulting isolation acts as a downward pull that makes further interaction even less likely. Many of us did not replace the social networks we lost with new social networks. Instead, we replaced them with Discord servers (where communities can still be built) and, when we go back to these platforms, with a quick, often-mindless catch up that leaves little space for meaningful interaction.

With the complaining out of the way, however, I’m sure that the lack of engagement is partly my own “skill issue”. Trying to understand how creators engage others on these platforms also made the “necessary grifting (affectionate)”11 stand out more, and, as it often happens, gave me a new appreciation for the nuances of content promotion.

I know this is not the exact semantic of the meme, but it does convey the mindset shift I’m having to do about “professional content creation”.

There is an art to growing a public in the current online world that I’m still trying to square with my own personality and priorities. While I believe it is possible to do this in a way that’s aligned to my own ethics, part of discovering it is unlearning a cultural mistrust of “those who want to build a public and their dirty tricks”.

One must imagine Sisyphus happy

The long story short is that I got sick for a couple of days a week ago, and my precious content schedule has been in disarray ever since. This post is late, the one scheduled for last week has been completely abandoned, and despite all this I still feel like I’m playing catch up. Pushing a boulder up a hill just to see it slide back down when you think the end is in sight is an apt metaphor for content creation, and this has become my standard response when I’m asked about my feelings on it all12.

In the past, when I worked closely with people who worked closely with “influencers”, I often heard stories of burnout laying just below the surface. Too many platforms to manage, the inability to stop under threat of newfound irrelevance, and the risk of parasocial relationships always looming made me wonder why would anyone even want to do this. If I hadn’t been forced into this position by my desire to change the trajectory of the web, I wouldn’t be here. At the same time, “just don’t do it then” would also be a loss: if important ideas are had in a forest and there’s no one there to hear them, do they make an impact?

With time, I hope my schedule will become more sustainable. After all, one of my main focuses this year is removing myself as the unfortunate (but still necessary) bottleneck of the projects I lead. Hopefully, I will soon be able to share the load of communicating the value of what we’re building, so I can kick back and return to shitposting about my blorbos. That is, after all, what the internet is truly all about.

“How do you do, fellow people?”

I’ve mentioned ADHD a couple of times already, and with good reason: nothing makes me feel the weight of neurodivergence as much as trying to empathize with what “regular people” care about does. Indeed, while “masking” and “hyperfixations” are most often discussed in regards to autism, ADHD people also often share these traits and the associated difficulties. And so, while I’ve made progress on aligning what I write with what I believe people want to hear–and I’m glad I did!–I still struggle with feeling like I even know what that is.

Like they do for many other neurodivergent kids, the internet and fandom gave me a space where my boundless (and often overwhelming) enthusiasm for whatever piece of media I was fixated on was not seen as “weird, if not a nuisance”. While I could (attempt to) seem like a professional software engineer in my everyday life, “online fandom” was the place where I could just be the way I am. After all, my ability to infodump about my latest hyperfixation at 100mph never meant most people wanted to hear me infodump at 100mph.13 That is, unless that infodump included very–let’s call them “colorful”–things happening to fictional characters.

Using my professional “regular person” skills to work on the spaces traditionally occupied by my neurodivergent self means I must learn how to translate between two dimensions that I feel were never meant to touch. When my current hyperfixation is reading 500 page business management books, it’s hard to engage the fandom world with that. But when I try to talk with “business people” about my work without fully reverting to a professional persona, I can feel them smelling the fandom gremlin on me. In the end, wherever I go, I feel like I’m straddling two worlds without fully being in either.

I don’t have a solution to this (yet). While I believe one exists, the beaten path often involves being so good at what you do that people are able to look past–and in a way forgive–your weirdness. While I don’t know whether I can indeed get there, I hope the content I’m writing will help me get these identities I’ve always separated just a little bit closer. If that ever materializes, I’m sure it will feel good.

The practical

With all those words out of the way, it’s time for some stats! With such small numbers it’s impossible to know whether anything has any significance, but who doesn’t love seeing some hard numbers anyway?

$upporters by platform

Here’s the $upporters stats for January:

I’m surprised at how much more popular Patreon is compared to my self-hosted option. I assume you really can’t beat convenience. The alternative is I wrote buggy code. Might be both!

Additional stats

Content reception

Most of the new $upporters came from the “enter the fujoverse” article, which makes sense because it debuted what me and collaborators have been working towards in a package finally understandable enough to support. Another small bump also came after the “LLCs vs nonprofits” article, which received little overall engagement but a lot of positive feedback by those who did read it (tl;dr: “I learned things I didn’t know I wanted to learn”).

A good percentage of $upporters came from people personally reccommending my work to others. If you ever wonder whether your word of mouth matters, the answer seems to be that it does. A lot.

My most popular post was “I made some pages in HTML and CSS, now what?”. I believe the eye-catching title has a lot to do with it. However, compared to the other two, this article resulted in no new $upporters (at least not directly).

My most successful stream was definitely “playing around with the Mastodon API”. I guess decentralization topics are very relevant to the current zeitgeist of people who care about the same things I do. We’ll see if this remains true with this month’s edition of “decentralization corner”, especially since we’re cheating on ActivityPub and learning @proto instead.

Final Words

Whether it eventually turns my projects into a viable monetary path or not, I’m glad I took the plunge and started this experiment in content publishing. This has been a learning experience, and hopefully will continue being such in the eleven additional months I’ll be doing this for. I hope by the time the year is over producing content will have become second nature, so I can continue reaping its clear benefits without feeling as much pain.

Until that happens, thank you for being on this journey with me. Onwards to February!


  1. “We didn’t do this because it was achievable with the little time we had, we did this because we don’t have a sense of what’s normally achievable in that little time (and then managed to pull it off anyway).”

  2. By ”they” I mean ”me”. I say this, and I’m not going to stop until others do too. If you don’t know what seme and uke are, just don’t worry about it.

  3. The reason my content is often delivered through flavor-text-heavy slideshows is that my thought patterns are very non-linear, which makes unraveling them for written long-form a struggle. “Aren’t you using these popup notes in a similar way though?” Indeed I am, glad you’re catching on. #ADHD

  4. I’ve been trying to die on this hill for a very long time: while there’s a lot of people reminding beginners that they don’t need complex set ups to start building with code, we don’t have enough people telling them that they–yes, they–can tame those more complex set ups and build things they can’t even dream of yet.

  5. This will be even more true once I manage to wrangle the hours of recorded content I have, and cut out the parts where I’m explaining useful concepts so they can be listened to in isolation. If this is something you’d be interested in helping with, please get in touch.

  6. The more content you accumulate, the more results you see from your overall content production. In an environment that’s less ephemeral than modern socials (like this blog), the content of yesterday continues producing value tomorrow, and the results from each piece of content build up on the ones created in the past.

  7. A lagging indicator happens when the results of the work you do today will only be visible sometime in the future. The hope is that good content now will eventually materialize in a sustainable public, even if some days this feels like a pipedream.

  8. These range from very simple things like “I can now maintain a calendar” to “I’m the queen of cold emails, just watch me cold email the Pope if necessary”. Incidentally, the second one was way easier to get used to than the first.

  9. (Tumblr voice)

  10. Eventually, having to understand how to navigate the “attention economy” is unfortunate but necessary. If you have content you want seen, you have to work to present it in a way that makes people want to engage with it more than other content out there. “Hate the game, not the player” and so on.

  11. The “happy” part of it is important. If I gotta push this boulder up this hill for a long time, you better believe I’ll figure out how to be happy doing so. I’m still pushing up a boulder though.

  12. If nothing else, having to produce content on a strict schedule has forced me to cut back on the length of my blog posts, which is helpful to both me and readers. No, seriously, I’m sorry my blog posts used to be that long (for both me and readers).