I always loved writing. The hardest part is to just pick up my pen, or launch my text editor. After passing that point of inertia and committing to it for more than 5 minutes, I get into the zone and feel the benefits almost instantly. The process is similar to that of physical exercise, where the toughest moment is to get up and put my running shoes on, or get to the gym.

With regards to the medium, I’ve used a number of ways to document my thoughts throughout the years:

  • Plain old txt files
  • Word documents
  • Emails to myself
  • WordPress, as a service
  • WordPress, self hosted
  • Wikis
  • Ghost engine, self hosted

I’ve wasted more time that I want to admit in picking the “right” platform. I decided that I will commit to one solution for the next few years, as long as it meets the following requirements:

  • It will allow me to focus on writing and need low to no effort to maintain.
  • I want to own the content and prevent platform lock-ins
  • I want a platform/process that has been around for a while, with the hope that it will exist 5-10 years from now (see Lindy effect)

Based on the above, the setup I’ll commit to is a static website, based on Jekyll that will be hosted on AWS using S3, Route53, CloudFront. The solution is not perfect and I already started exploring the possibility of moving to WordPress.com, Squarespace or the Tel-Aviv based wix.com, but each of these platforms has its own pitfalls.

The benefits of the Jekyll / AWS-hosted approach are:

  • Focus on writing: This is a big one. All I need to do is launch any editor and write without needing a browser. I can (as I am, right now) do it offline, see my changes locally and publish at a later point.
  • Low maintenance: While not zero maintenance, it doesn’t require much. The publishing process is as simple as running a script that syncs the Jekyll-generated site to an S3 bucket. That’s it. Maintaining the AWS services involved is also simple, even though having to think about the infrastructure is a big drawback.
  • Owning the content and preventing lock-ins: Jekyll produces minimal HTML webpages that I can easily import elsewhere. Also, contrary to platforms like Medium, I’ll be the sole owner of my content.
  • Will it work in 5 years? From what I understand, Jekyll is mostly in maintenance mode but my bet is that it will still be around for the next few years at least.

What if Jekyll gets abandoned, starts breaking or you’ve simply had enough managing AWS infrastructure?

In that case, and my plan B in general, is to switch to WordPress. Wordpress is here for a while and it is here to stay - currently 40% of all websites are powered by it, which is nothing short of impressive.

The obvious question here is, why not move to WordPress and just get over with it? The platform has been around for many years (almost 20) and is supported by an organization that has spent countless man-hours in perfecting all aspects of the online writing experience.

To answer this, I’ll take a step back and ask myself - what do I want to get out of the writing process? The answer is that I want to form two habits.

The first habit is to use an online, personal notebook where I can upload my thoughts and notes. It has to be online, because:

  • I want to practice posting even if noone will ever read the blog.
  • I want my notes to be accessible from everywhere.

There’s something in the act of putting your words ‘out there’ that can’t be replicated by simply writing in an offline, either physical or digital, notebook.

The second habit is to engage in online communities that I’m interested in and make my writing process interactive by accepting and giving feedback. For this, and that’s the key take-away here, I will most likely use some of the available platforms and ride on their network effects.

In closing, there’s no dichotomy; I can have both a self-managed space and a presence in some more popular platform.