This essay originally appeared in CT No.65: The obstacle course of a website redesign along with a review of proximity chat app tool Gather.

Let’s start with the ingredients. This build started with:

  • An existing Ghost website with approximately half of my content already loaded in
  • A Substack site with a mailing list and all my content all mushed together
  • An audience with expectations that I publish a certain type of content on a semiregular basis, some of whom want to dive deeper than others
  • Loosely established content pillars, metadata and content types (i.e., essays and reviews)
  • An indeterminate non billable period before client projects would pick back up from the fall slump (I thought it would be 8 weeks but it turned out to be 3)
  • A rough deadline of “for this to be feasible it needs to be turned around before the end of the year and we are already 3 weeks into Q4” (how tech industry of me)

I expected strategic planning to take a bit, but I know some things, so it was probably the easiest part of the whole thing. The Membership Guide was invaluable in helping me research the components I needed to think through on adding a new community aspect to my business. I also deeply understand B2B media and the whole creator/newsletter economy, and I literally wrote my master’s thesis on blogging startups, so, yeah, I just made extremely informed guesses for the following questions:

  1. How much content should be behind the paywall? I went with around 30% of the essay content (or every third essay), with all reviews always free. Guides are behind the free membership paywall. “That’s not much content!” you say, but I’m a new brand, and I have a reader acquisition strategy based largely on organic search.
  2. What should I charge? The ancestral newsletterers have set the going rate between $5 and $10 for a monthly membership. I went with $7/month or $75/year, keeping my free founding 1k members policy, of course.
  3. What’s my navigation and content surfacing strategy? Some people dream about building baseball fields and billion-dollar businesses; I dream about redesigning my website’s information architecture. Pretty much the second I launch a website I immediately envision a new IA. After dissecting analytics for how visitors were (not) using my previous nav, I settled quickly on topic-based nav items with one added point of hand-curated related content beneath each post. Audiences search and think through topic-based nav more quickly than thematic- or content type-based navigation.

Once those questions were settled, I began actually building the thing, which presented its own set of obstacles.

1. Adding structure to unstructured content

Unstructured content is a pile of words and images that are interconnected, but relatively indiscernible when read by computers. PDFs are considered unstructured content: a pile of words and images on a page that can’t be separated from each other. You can add metadata to a PDF, but you can’t break it down into its component parts.

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