Writing is challenging. Being creative, more so. Add in the pressures of a weekly production schedule and you have a recipe for unexpected results. This is the challenge I took on.
Late in 2023, I stumbled across a Skool group about minimalist hustles. (Skool is a community-based education platform). I’ve always resonated with the minimalist concept even though I’ve never put it into practice (at least, that's what I've told myself!).
The owner of the Skool group has been producing a daily minimalist hustle newsletter for a long time. And advocating on the positive compounding effects that multiple minimalist hustles can provide. Many “small bets”, if you will.
For my writing, specifically non-fiction, I’ve tried to be simple and efficient. Say what I want to say with as little effort as required to do so. Why waste words? Multiply this across a few projects, and I thought I had my immediate writing future set out - I was going to start 2 newsletters. If I kept them somewhat minimalist, how difficult could this be?
The next challenge was selecting the topics to write on. The first one was easy. I am a generalist. I have many and varied experiences and knowledge on numerous topics. Could I teach a class on each? No. But I can talk on these topics and have conversations. I know enough through lived experiences and interests. That was my thought process for this newsletter - a group of like-minded people having conversations on various topics.
At around the same time, I discovered fountain pens. More precisely, I learnt that the days of messy inks and stained fingers need not be the norm when it comes to fountain pens. Fountain pen ink cartridges are a thing - just like ballpoint refills. And I was hooked! Googling on the subject brought up some beautiful pens. Works of art, some would say. With prices to match. There are pens priced at all levels and attainable. Others, completely out of reach for most. Most importantly, however, I had my topic for newsletter #2.
I elected to publish on Substack after briefly reviewing my options, and decided on both being weekly newsletters. One published on Wednesdays and the other on Saturdays. I started the Generally Speaking newsletter first, as I had content ready to go. I had immediate experiences that I wanted to relay, hoping that others would identify with it. Initial going was slow and subscribers were trickling in.
Some weeks later, after I had bought a couple of fountain pens and notebooks, The Fountain newsletter was born and my journey had begun in earnest. And I had yet to understand what I was in for.
If you’ve ever tried to write a newsletter with any sort of frequency, content planning is important. Critical. You need to have content for weeks or months into the future. Just having something for the next edition won’t cut it. What if you don’t like it or how it’s turned out? What if you can’t make it work? Not having a funnel of content to choose from means that you have to settle for what you do have. This doesn’t allow you to do your best work. And for the first few months of these newsletters, I was living paycheck to paycheck.
As my content funnel grew, it began to crystallise for me. My fountain pen newsletter was going to hit a wall. And soon. Fresh content was limited. There’s only so many areas you can talk about with fountain pens. I would need to be buying new pens regularly and writing about them. Doing pen and handwriting comparisons. This was the “low hanging fruit” for my topic. Am I destined to become a review newsletter? This wasn't what I'd signed up for. I wanted to relay experiences. I was supposed to document my journey into the fountain pen world and everything that came with it.
When this realisation hit me, my world changed. Upon starting the newsletters, I strongly believed that the fountain pen newsletter had longevity and would be the one still going in 12 months. After all, it was the one that had the greater readership and subscriber base, double of the generalist newsletter. But, numbers can be deceiving. I now knew that this wouldn’t be the case. With over 30 issues in the bag, I knew this with certainty.
The problem was, however, that by this time my generalist newsletter had stagnated and I hadn't produced a newsletter in some weeks. After 24 weekly issues there was nothing on the horizon. I wasn’t enjoying the ideas I had in the funnel, and took an informal break from the newsletter. It was at this point that I decided to change the format and pivot slightly to a newsletter focused more on thinking. Some of my generalist content was still applicable, but I wanted to document processes of thinking and the tools people used to help them.
My idea was that the revamped newsletter would primarily include a main article from myself and a few curated from others on the topic of thinking. I had already reached out to people I thought would fit the newsletter and had their agreement to repurpose some of their content. Additionally, I felt that a weekly cadence was not sustainable for this type of content and I would move it to monthly.
So, I had one newsletter on hiatus, looking to change direction, and the other quickly hitting a wall on content. Managing 2 newsletters didn’t seem like such a great idea now.
Fast forward 3 months, and the status quo remains. People are still discovering both newsletters and subscribing, which is encouraging. But only one has a chance to make it back with any sort of regularity.
I still don’t know how I’m going to move forward with either newsletter as I write this. When I started, I was cognisant that the pressure to produce was something I didn’t want. I didn't want it to feel like work. If it ever got to that stage, I’d shelve it, I told myself.
This is where I find myself today. The fountain pen newsletter, with any regular cadence, is done. I’ll produce some adhoc editions in the future, but these will be for me as I see fit. The revamped generalist/thinking newsletter is yet to take shape. But I'm still hopeful.
Writing is challenging, especially when you need to create content to serve an audience.
Take small bites.
