Overcoming Blogging Friction

March 1, 2015

I’d like to post more, but I’m afraid that my current web host gets in the way of that.

This site is hosted on Square Space, and has been since I moved my web presence from Rose-Hulman in a hasty transfer back in 2011. I’ve been pleased to have Square Space manage all the details of keeping the site up, staying on top of security updates, and generally handling all the sys admin work for me.

The trouble is friction. The amount of ceremony to post an article or share a file is just too high.

I write in markdown using BBEdit on my Mac. To post an article to Square Space, I have to upload any images through a point-and-click file upload interface. Then I get the links for the images through some more clicking and copying. I update the post on my Mac with the image links. Then I click some more on the web site to create a new article. Finally, I copy the markdown source of the article into a text form on Square Space. Any updates to the article require a similar series of hoop jumping.

So, inspired by my colleague’s posts last fall, I’m starting to re-think my approach to this site. Unlike Brent, I need everything from hosting on up.


Whatever system I choose, it needs to meet a few requirements:


There are a few other features that I think would be cool:

Roll My Own?

I’m not averse to rolling my own system, though I’m more comfortable writing code than configuring servers. Still, something like Marco Arment’s Second Crack or Brent’s system appeal to my engineering sensibilities—clean, simple, and to the point.

Does wordpress.com meet my requirements? I’ve poked around their site, but they sure don’t want to tell me what’s possible. They just want to shout about how easy their system is to use. I’m afraid their “easy” is the kind of friction I’m trying to escape.

So, what’s the answer? Who should I be considering for hosting? What tools should I use for publishing? Suggestions? Let me know!