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I finally created a system for regular mailings with a plugin for Obsidian that automates tracking my posts and preparing newsletter content, even though I'm still refining the process.
improve newsletter content automation 
#japandev
Made new newsletter 
#goodmonday
Collected content for newsletter #goodmonday
improved newsletter template 
#ekh
Updated 
#thebrainpsych after a long time. First, improved "initiatives" section with card design. Second, fetching blog data from my newsletter instead.
update about content for newsletter 
#fajarsiddiq
send newsletter with updates
repurpose newsletter into article 
#freelance
Finally shipped updated newsletter template and frequency 
#rubyonremote
Pick content for next newsletter #goodmonday
tweaked newsletter production process
started writing newsletter #ekh
/done weekly newsletter content 
#stackbrief
Scheduling first newsletter with recent upgrades on 
#quickactions
Prepare new newsletter stuff 
#perspectiva
start drafting content for upcoming newsletter 
#sunday
Send latest article to newsletters 
#ss
working on newsletter
Edit newsletter updates 
#jovial 
#stateofdevs