Personal Retreat Technology

A few days ago, I published a video about my personal retreat experience. Since then, I’ve had many people ask me to explain further what technology I used. I’m about to explain what I did, but before I do so, there is a good argument that you shouldn’t take any technology on a personal retreat. It’s so easy to let the tech take over.

However, in my case I wanted to do a lot of typing and dictating, and tuning out infinity bucket apps has never been a problem for me so I brought along some Apple gear. If you want to bring technology and are worried you’ll be wasting time in social media instead of doing the hard work of a personal retreat, turn off your WiFi and cellular radios. I didn’t need to get that drastic, but if I’d caught myself lurking on Twitter, I absolutely would have done so. (I also did bring along pen and paper, just in case.)

If you are going to use technology, there are three phases to my version of a personal retreat:

  1. Identifying and writing out your roles.

  2. Asking tough questions about each role.

  3. Planning for action in relation to each role.

For steps one and two, you could do this with any tool for managing words. A text editor would be fine. Apple Notes or even TextEdit could get the job done. The next level would be an app that supports headings and organization, like Drafts, Ulysses, or even BBEdit. As I explained in the video, the process is very non-linear. You’ll find yourself bouncing around among roles and questions a lot. For that reason, another excellent tool for this process would be an outliner or mind mapping app with both the ability to add plenty of text and folding branches. My two favorite apps for this process would be OmniOutliner or MindNode.

For this past retreat, I spent the first two days using Roam Research. I’ve been experimentally using Roam for a few months. It’s a powerful tool that combines the ability to turn anything into an outline with the ability to link any outline block in your Roam document (“graph” in Roam parlance) to any other outline block in your Roam graph with no friction. Roam is an excellent tool for this process … except for its immaturity. While Roam is a bit of a mind-bender and makes connecting thoughts very easy, it is still very new, and there are a bunch of parts to Roam that are not ready for prime time. My biggest concern is the lack of security. As I started to pour my heart into the retreat document, I became concerned about lack fo security in Roam, a web app, and ended up towards the end blocking and copying into OmniOutliner, which lacks Roam’s cool backlinks but has better security. (We’re going to be digging in on these research tools on an upcoming episode of Mac Power Users, and I’ve got a lot more on my mind when it comes to Roam and its competitors.)

For part three, turning my retreat ideas into action, I relied heavily on OmniFocus and Drafts. A lot of the process toward the end was writing plans out for myself and my collaborators. All of those started as blank text files in Drafts and grew into much more as I worked through the process.

I also set up a series of new repeating tasks and projects in OmniFocus to help keep myself accountable for some of my planned changes. Using a set of custom perspectives and review frequencies, OmniFocus can help keep me honest.

Looking back, my personal retreat technology wasn’t particularly novel or demanding. You need a place to write words down. You need a place to turn words into future actions. To go much beyond would probably just be a distraction on a retreat.