Single-session Publishing
In my first 100 days post-WOP, I wrote every day and basically published nothing.
What helped me snap out of that rut was to take on a mindset of "single session publishing." This means I sit down for a writing session and don't stop until it goes on my site (sessions were 2-4 hours). They were effectively first drafts, and sometimes I'd come back to revise them. I didn't "blast" them to my email list, but DM'd them to specific people to start a conversation. There was something about having a body of work on my website that took the pressure off (eventually) sending essays to my larger list.
I'm 100% a perfectionist, and think it's worth having a rigorous, increasing quality standard, but it's important to also have places with much lower standards to serve as your release valve.
Also, publishing under my legal/professional identity came with all sorts of psychological blocks that were completely invisible to me until I started publishing under a pseudonym. Every situation is different, but I wonder if shifting to semi-pseudonymous Substack would help take the pressure off everyeone.
I’m sort of inspired now to create a section on my own Substack called “Drafts.” You can customize that so new subscribers by default aren’t on that list. I currently have an “Experiments” section on my site, but “Drafts” feels a lot more self-explanatory. (Some of these drafts will eventually reach “peak” form and get reposted in the Essay section, but that won’t happen with most of them).