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Writing is Creating
This newsletter started on the premise that writing is thinking. After putting pen to paper daily for the last 3 months (and actually publishing ~ 2 times per week), I’ve realized that bootstrapping it was akin to launching a new product. And after hitting my initial sign-up target, I found that sustaining it required a run the business mindset.
What I’d like to share today is the structured approach I’ve been using build a readership; if you’ve ever attempted to produce something of value, with quality, at scale, for an audience, this will resonate.
creation and distribution are distinct activities
collaboration is the only way to scale up and out
you have to experiment with different channels
user engagement prevents monotony setting in
an acquisition funnel requires time and/or money
quality takes investment and forces trade-offs
real value compounds and amplifies over time
Let’s walk through each of these dimensions in detail:
 Creation vs Distribution
I chose Substack as the platform for hosting this newsletter because it’s designed as a product for writers, and it let’s you evolve your audience as you see fit (free sign-ups, paid subscriptions). Having previously tried Quora for blogging and LinkedIn for publishing, I realized the former is interested in being a knowledge repository and the latter a professional network - both of those missions only tangentially intersect with an individual trying to produce content for a target audience, so my needs as a writer felt un-met.
While I’ve been very happy with Substack as my home base for the distribution of my posts, I’ve felt the need for a more purpose-built tool for ideating and iterating on ideas. I have > 100 draft articles on Substack, and while the web editor is full-featured and the mobile view is not lacking, I find myself wanting to sketch out ideas a bit before sitting down to finalize and publish. For now, I just use a notebook given my Luddite tendencies, but I’m strongly leaning towards Notion as my app of choice to formulate future posts and create a more coherent story arc. I’ve also heard good things about Coda and Roam, but have yet to try them myself.
 Scale Through Collaboration
At some point you’ll realize that you alone can’t produce enough content to sustain an audience. If you’re writing just for yourself as a way to clarify your thinking (this is how I started), then you’re fine; however, if folks find value in what you’re publishing and want more, you’ll struggle to meet that need without a significant time commitment. If writing is a side project for you, there is a risk it’ll fizzle out - you won’t create enough to get a feedback loop going, and that lack of positive reinforcement causes you to lose energy.
One way out of this conundrum is to stop trying to do it alone. If you work with others who are on a similar mission, there’s a support system in place. Some of the things I’ve started to leverage are writing groups to share best practices, polling readers to brainstorm topics, and chatting on Twitter with writers who do it full-time. My next experiment is to co-author articles with very engaged readers, and eventually think about a newsletter bundle (one curated mega subscription vs ad-hoc individual streams).
 Channel Experimentation
One thing I believe in is products are built to fit channels. I’ve gotten almost no traction with threads on Substack, but that format works nicely on Twitter. I’ve published the same post on LinkedIn and Medium with a 10x difference in clickthrough - leveraging an existing audience is way easier than building a new one. Every channel has its idiosyncrasies, but how can you possibly produce content that’s optimized for each distribution method? I focus on the thoughtful Substack posts, and then slice and dice for other platforms: threads on Twitter, aphorisms on LinkedIn, etc. You also can stretch one article out several days given the pace of content cycling - it’s likely folks didn’t catch it in their feeds when you first posted, so you have to bump up multiple times and use other influencers to amplify (don’t hesitate to engage with subject matter experts in a dialogue around your idea).
The other thing I’ve realized is that certain formats work better across publications. My creative essays do well on Substack, but certain dense topics are a bit much for an email newsletter. Eventually, audio and video have to come into play, in both snippets and long-form. On that front, I’ve started to dabble in podcasts (coming soon!) and hope to get over my camera shyness before the end of the year. Lastly, there are simple teasers (like a Tweet) for your essays, and then there are indirect lead-ins like a Quora answer - I find the former is great for short-term traffic generation, while the latter helps with the long-tail.
 User Engagement
The most rewarding / most difficult aspect of writing is getting readers to engage. LinkedIn has been the best platform by far on this front, and that’s because the reach goes well beyond my 1st-degree network - posting something topical and trendy can get attention for several days in a row. Substack hasn’t been too strong a source of comments / favorites, and my current theory is that people read the email newsletter on their mobile devices, and clicking through to the website to respond is too much friction. I’ve actually had people respond to the email, and it’s a strange sensation to have a thoughtful back and forth over email (vs in an app like Twitter).
Subscribing to other newsletters is actually a great way to observe how others are tackling this problem. One common technique, once you’ve got enough of a content archive, is to send readers a “best of compilation” (usually at initial sign-up). Pictures are also great visual cues, which is why I’ve actually kept up the “childish drawing / interpretation” routine to end my posts; multiple readers have told it’s a memorable gimmick, and if you’re cross-posting on other platforms like LinkedIn / Twitter, images will boost click through rates significantly.
 Acquisition Strategy
The highest ROI strategy I’ve utilized to get sign-ups has been direct outreach to prospective readers, usually via LinkedIn, but also email / Twitter. What I basically do here is identify ~ 5 people per week who I think would actually enjoy my writing and then reach out to them with a hand-crafted note. My criteria for reaching out to folks is either (a) they tend to be industry experts on the topic I’ve written about or (b) I’ve worked with them before in that sphere. The response rate is a heartwarmingly high 80%, and a meaningful 20% will go above and beyond with very constructive feedback.
The internal debate I’m still having on this front is nailing down my niche. Since I started writing for myself, the topics and style tend to meander, and the consistent feedback I’ve received from professional writers and editors is to have an actual target reader persona in mind. My most popular most by far is a collection of tips on public speaking, and the broad appeal likely correlates to how well the article performed, but it’s hard to generate such mass market content on a regular basis - individual experiences just can’t be up-leveled and genericized to that degree. My next step here is to step a little outside my groove (product builders in tech) to see what adjacent reader bases there might be, and that might require actual acquisition spend (e.g. marketing campaigns) beyond elbow grease.
 Crafting Quality
By far the biggest mental hurdle to publishing (not writing, publishing) has been the voice in my head saying “this isn’t your best work…what would Mrs. D’Souza from 7th grade Language Arts say?”. To get over my initial hang-up and actually launch this newsletter, I ignored Mrs. D’Souza. But quality matters. I can’t quantify it, but my ability to broadcast and amplify any article is a function of how crisp my writing (and thinking) on the topic was - when you know you’ve got a great post, the distribution comes easy. The other thing I’ve come to appreciate is that regular, interesting content beats all the other “growth hacks”.
My approach so far has been to write regularly (literally every day start a new post or tweak a draft article) and publish when I run out of edits. My editing right now includes a lot of re-reading while writing and actually putting drafts aside for a day or so and coming back with fresh eyes. Ultimately, there is no substitute for an actual editor - I’ve had folks message me pointing out simple typos and grammatical goofs - you just miss things when you’ve been starting at it forever. Editing is its own craft, so a structured guide / automated tooling is actually a good investment on this front.
 Compounding Value
The last insight I’ll offer is the compounding value of not only a good article, but also a growing collection of quality writing. An evergreen post you can leverage multiple times vs just at the initial publication. When the topic comes up organically, you can refer folks back to your write-up. I’ve actually gone back and added new sections and additional references to existing articles when readers help me rethink things week / months down the line.
Additionally, once you hit a critical mass, a flywheel effect kicks in. For my first 2 months, I was doing direct outreach AND publishing 3-4 times a week to show a certain pace of content creation for new readers. But the last 1 month I’ve only been posting 1-2 times a week AND barely been doing outreach, yet the pace of new sign-ups has actually accelerated. Since Substack lets me see what posts lead to new subscriptions, I’ve noticed a pattern around older content actually generating leads. The idea of today’s output leading to tomorrow’s outcome is a pet principle of mine. Finally, once you have a compilation, you can open up other doors like traditional books, speaking engagements, and coaching opportunities.
Hopefully this playbook inspires others to switch from a consumer mindset to a producer ethos - I firmly believe after doing this for 90 days that writing is creating.
I’d love to hear from readers who are starting or accelerating or resurrecting their writing journeys - please chime in via comments👇. And if you enjoyed this post, please consider subscribing.
further reading / references
David Perell on Twitter has been a great motivator to write persistently
the Blogging Guide newsletter is full of tips and tricks when you get stuck
Substack regularly offers webinars by / for writers via Crowdcast
curation is a form of creation, if you apply the business model of good taste
Ben Thompson’s Stratechery blog makes excellent use of visual aids
one tool I’m looking at for quick / professional graphics is Canva
the business lifecycle explains why engagement drops as audience expands
another writer’s deconstructed process, including the thinking/writing loop
First Round offers a founder’s perspective on why effective writing matters
interesting advice for newsletter-ers: divide into seasons, ala TV shows
I use these 13 tips for making the switch from consumer to creator all the time
childish drawing / interpretation