100 Newsletters: Slow and Beautiful Growth 🌱

A history of writing online, lessons learned, and a look at the numbers

Greetings from Éire, the island of saints of scholars. This week’s landmark 100th edition comes to you from the sunny nook of my third floor bedroom, and I hope you will enjoy reading it every bit as much as I enjoyed writing it ❤️

Today, I will share my reflections on reaching a century of newsletters, an achievement which didn’t always seem like a sure thing. The process of growing my newsletter, just like growing these little tomato seedlings, has been slow, uncertain and messy, but also beautiful in the most organic way possible.

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Gentle Reader,

Issue #100 is upon us, and I was genuinely never sure I would make it this far. Along the way I faced several headwinds, but with some nods of encouragement here and there, I managed to keep on trucking.

The idea to write 100 newsletters started out with an idea from the famous Visa, on the website formerly known as…you know the one. His concept was simple: to become good at something, do it a lot.

I guess the number 100 was somewhat arbitrarily or instinctively chosen by Visa, as a good round number and a natural milestone in our base-ten numeral system. 50, for example, doesn’t feel like quite enough, and 200 feels like overkill, if the goal is to get a good foothold.

It’s also self-selecting. If you look at podcasts, 90% of people never make it past episode 3, and 99% never make it past episode 20. If you manage to get to 100 of anything, it probably proves that you are independently interested in the topic, and doing it for the right reasons. It’s hard to do 100 of anything without enjoying the process.

If you write once a week, this ends up being a commitment of almost 2 years, to reach 100 issues. In my case, it took me longer than 2 years, because I didn’t always turn up, especially in the early days. It’s better to establish a rhythm and regular cadence – a small bit of discipline, even for a labour of love, goes a long way.

A look at the numbers: subscriber count

Since I love reading about other writers’ journeys, I have taken the liberty of including a little section on the numbers behind the newsletter, in the hope that some might find it helpful or interesting.

In terms of subscriber count, the level of growth has been very modest, and I think if I was writing for growth alone, I would have given up long ago. I’m writing for pleasure, but also connection, so I do love it when I get new subscribers, but the growth of my newsletter should not be the primary focus or, stated more accurately, growth should not come at the expense of my enjoyment of the work.

As of today, I have 111 subscribers, having started with…4. These 4 steadfast followers were imported from my previous blog on the internet, of the same name, long since mothballed. I’m not sure how many articles I wrote over there, perhaps 30 or 40.

Observe the first half of the chart: you will note that I wrote to basically nobody for years. A sign of madness perhaps? The first little bump in readers came when my friend

Paul Millerd

shared my Oxen of the Sun article about modern work, in an issue of his newsletter entitled Ten Things Worth Reading. This doubled my (very small) readership.

Later, you can see some very slow growth followed by a dip in the chart, from when I removed inactive subscribers, whose unwillingness to open my emails supposedly increased the risk of my newsletter being marked as spam. Possibly this advice was misguided, or cunning sabotage delivered as fake news, and I will probably never remove a beloved subscriber again.

As slow as the growth has been, much like my little tomato plants above, I’m happy with where I’m at. The eagle-eyed amongst you may notice I don’t have a single paid subscriber yet, and so there is glory to be had for somebody very clever who sees the opportunity to become my first ever paid subscriber. When i become rich and famous, this person will be able to claim to have fostered my talent at an early stage.

Now that you have seen how the sausage gets made, let’s take a look at some of my writing history, and the lessons I have learned.

My personal writing history

Notionally, my history of writing began in the online space a few years ago, with my previous blog. In reality, my love of the written word, and my desire to squiggle things on pages, long since predated my first article or newsletter. In school, I was always the one who loved writing, who knew the meaning of strange words, and who experienced a sudden frisson after witnessing a well-placed semi-colon.

In the early days of the internet, I used to love reading and writing on discussion forums. My mind was blown by the ability to log into a website and ask a question, and get an answer, from anywhere in the world. Nonetheless, it never occurred to me to start a blog. That was something other people did, whose powers and capacities were somehow different, or who had something very concrete to offer, like financial blogs such as Mr Money Moustache.

An unfortunate truth about the human brain is that we often miss things which are hidden in plain sight. Sometimes, some gentle encouragement, prodding and redirection is necessary, which is why I’m a fan of online groups and communities.

Now that I write online, what changed? I now appreciate that if you have a point of view, you have a ‘point’ and you can share it. As somebody who used to always base my decisions on data, I have come to love perspectives even more. Reading somebody’s take on something, moulded by their life experience, is a lot more interesting to me now than an expert preaching from the pulpit on their niche topic.

Real human voices are what I value, and Substack seems to be doing a good job of giving them ventilation.

What I have learned

A good piece of advice is to not act on advice from anybody, but to receive it all, mull it over, and see what works for you. Having said that, here are some nuggets I can offer up, based on my own experiences with writing online.

Ask yourself: what is missing?

I am guilty of diving into a topic without providing the necessary context or back-story. The human mind seems to be hard-wired to do this – once knowledge is attained, it is immediately taken for granted, and also assumed to be available to everybody. This is not the case and, even for those well-versed in the topic, a gentle introductory paragraph serves as a limbering-up exercise and a reminder of what will be covered.

It’s important to prep the reader

Following on from this, I also like to include a very short overview, even if only a sentence, about what I will actually write about in the particular issue. In the beginning, I was so vain that I didn’t do this, assuming that everybody would want to read it, regardless of what the topic was about, because my writing was just so good (see below). This turned out to be a bad idea.

I’m not as good as i thought

This one is a bit of a kick in the guts to admit. If you look at my subscriber count, you can see how slow it has been. Possibly, my writing style didn’t suit the platform, or I didn’t market myself, or a hundred other reasons. But the real reason, which is hard to hide from, is I’m just not as good a writer as I thought I was. When I read back on older posts in this newsletter, I cringe a little bit. This is normal and healthy, and at least I’m getting better. I started off too complacently, assuming that people would just read my writing, even if I didn’t make a concerted effort to tidy it up, to fix the headlines, to make it platform appropriate, and to provide some kind of specific value for the reader.

Have good titles

It also hurts a little to acknowledge this, but the titles I personally very much enjoy are not good titles for Substack articles. They need to be catchy, a little bit clickbaity but not too much, and they need to suggest or describe what the article is about. I had a tendency to use titles which gratified my own aesthetic sensibilities, which were terrible. Looking back at previous choices, some of my articles were called ‘Gentilezza’, ‘Bonjour’, ‘Computer Daze’ and ‘Enttäuschungsprophylaxe.’ What the hell are those articles about?

Find a way to promote yourself

Obvious advice: even though I haven’t taken this advice myself, it’s true that if you don’t promote your writing somehow, people will not find it and read it. This leads to shouting into voids, a favourite hobby of mine.

What is the best way to promote? It seems that the best way is to already have a big following elsewhere, such as on social media, which you can redirect to your writing. How do you develop a big following elsewhere? I have no idea, but I know that ‘build it and they will come’ is not true.

Feedback is fast

The great and terrible thing about writing online is that feedback arrives immediately. If you drop a banger, you see those likes and views coming in very quickly. Unfortunately, if you drop a stinker, you will know very quickly that the algorithm has realised the puniness of your effort, and the tumbleweed will roll in accordingly. This can be very useful and also very dangerous. Personally, I find it exciting, but it also seems to interfere with any attempt to write offline, as I don’t get the benefit of the feedback loop, and I run the risk of producing indulgent and meandering content. In this respect, I seem to benefit from the kick up the arse offered to me by the online space, which helps me to remain pragmatic in my writing.

Don’t worry about repetition

I used to be afraid of covering the same topic twice. Then, I realised that everything I read online is basically the same 2-3 topics again and again, in different guises. Readers actually like repetition, to a certain degree, because, as mentioned before, it is the perspective that is interesting to them.

It’s also correct to assume that every reader has not read everything you have written. Now that I have backlog of 100 posts, it’s safe to say that many of them will rarely be read, or reread, and so new readers will likely not notice or care about something that could be received as repetitive.

Looking at some of my articles where the themes are very similar, I can nonetheless see an evolution in my thought process, and this shows that repetition is a key part of iteration, which helps us to grow, in writing and other skills.

Find a way to enjoy it

I mentioned above that I have not earned a single euro from my writing. I am here on this sunny Saturday morning, tapping on these keys, reader, because I enjoy it.

I genuinely love writing this newsletter and sometimes I have to hold myself back from trying to write it midweek. It was not always like this. Growing as a writer, getting a few more voices and subscribers into the mix, and becoming more confident in what I put out there has helped me to love the journey.

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THANK YOU!

Gentle reader, regardless of whether you are a subscriber or not, and regardless of your class, creed, conviction, whether you are tall or small, shy or brash, regardless of how you like your eggs in the morning and regardless of how you think they put the fig in the fig roll, I want to say: thank you! For reading this or any other article I have written, for being with me on this journey and for giving me the strength and spirit to keep this practice going. ❤️

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My 5 most popular posts

5 little treats for you:

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Thanks again, and I hope to see you next week, same bat time, same bat place, for Part II of my financial journey.

Affiliates: I recommend the Supernote e-ink device, which I use for reading, writing, and annotating documents. This affiliate link is only valid for EU customers. I am also affiliated with the Pathless Path Community, which is a beautiful online space where we focus on working meaningfully, sharing creative projects and growing together.