That a common nightmare for many of us who are more in love with the setting-things-up part of every endeavor!

It's not as bad when you keep it as simple as possible. The first version of the 'generator' for my blog (shameless plug: rubenvannieuwpoort.nl) was written in one or two days. It's just a couple of bash scripts (and one Python script), really (see https://github.com/rubenvannieuwpoort/static-site-generator). Now I haven't wrote a lot since, but that has to do more with perfectionism and being busy).

It's ok, "Writing essays doesn't have to mean publishing them."

http://paulgraham.com/useful.html

However, publishing is not free, you pay in money, your ownership of the content or your viewer's privacy.

That's if the publisher is actually decent and their mechanisms work.

I was addressing the perfectionism - which paul graham's article talks about in a counter intuitive way (sort of "we will not serve a wine before it's time")

As to "paying" I was trying to think of venues where you can publish without compromising.

I think the answer might be something like a $5/mo droplet or something on a cloud service.

There are nice venues to publish free, like here on hn, but you lose control of your work - for example, it could be taken down, it could be heckled, etc...

This is oft-quoted but it's what always happens when I sit down to write something - https://imgur.com/gallery/rQIb4Vw

Wait, something's slightly off with kramdown - this isn't right - 12 hours later you're recompiling to update dependencies, and your version of ruby is out of date.

This is Jekyll specific, so YMMV - but if you're like me, probably not by much.