New Beginnings #1: Leaving work

This is part #1 of a 3-part of a series looking at how I used GTD and OmniFocus during my recent country move. This article looks at the challenges of leaving work and how to leverage OmniFocus and GTD to make the process easier.

I've recently moved out of Ireland, leaving my first job and an apartment. Even though the process wasn't as difficult as you might imagine, any big change comes with difficulties. The organizational tools and techniques at our disposal are meant to help us out during these big transitions. So how did GTD and OmniFocus fair in helping me get through the transition? I want to evaluate what worked and what didn't work, so that I can adapt for next time. Hopefully this will be useful for you too.

This will be a three part series covering the three stages of moving:

  1. Leaving my job
  2. Leaving the country
  3. Building a new routine and focusing on new goals

Let's go!

Leaving work

Thanks to GTD I was able to successfully progress 5 high-visibility long-term projects, including the development of apps to help the group manage their time, and larger research projects with external clients. The transition had to be as smooth as possible.

In practice, this meant finishing any critical pending work, producing detailed technical documentation, making any project-related materials available to others, and showing the people taking over where all the skeletons were hidden.

The natural planning model shines with these kinds of projects, where there are lots of interconnected parts and a clear path between right now and the goal. With that said here are a couple of things which helped bring my work to a close and even hit some of those Someday/Maybes.

Mind sweeps

I broke out the pen-and-paper and made several mind maps that detailed everything that needed to be done for each project I was handling. I don't tend to follow any particular structure or formal set of symbols, I got with whatever I feel like at the time. The goal here is to dump and jog the brain into coming up with things that need to be done you didn't know where there. If I can't come up with anything else I start to collate all the nodes into projects and tasks in OmniFocus.

Projects included documenting all the code, sending the latest changes to the central server, uploading documents to the group's intranet, and deleting all work-related files from the laptop. It might seem simple but keeping track of the how "closed" each project was could have been a nightmare.

Project Scoping

Documentation was a particularly difficult task to tackle across 5/6 different projects1. How much documentation is enough? I had a limited amount of time so the trick was to define lean goals.

Instead of goals like:

Have full documentation of application X,

I focused on making sure that the person taking over was as comfortable as possible and the project goal/name became:

Carl is comfortable with taking over project X.

This way I didn't spend time and effort documenting areas which were clear to Carl2, while being open to elaborate on aspects of the projects which I had dismissed as trivial.

Set boundaries and make sure everyone knows

I wanted to finish as much pending work in the time I had left. I had to pick exactly what to work on and set limits with my colleagues and superiors. The message was clear:

No new work unless it is critical

This is crucial. You want to finish as many projects as possible, not create a bunch of new ones. Aim to have everything done a few days before, that way when things turn up last minute you have a buffer.

And now for a little more

Thanks to keeping track of all the moving parts I finished everything a day or two before I was due to leave. This brings us to the fun part.

As I worked on the various projects I would naturally come up with new ideas or things that would be nice to have. Many great ideas ended up on the Someday/Maybe pile. Things like cleaning the code base, or improving the performance of the apps we were building.

In my 2 "free" days I got to finish 3 of these Someday items, which felt great. I exported the rest of the Someday/Maybes to a text file which I then gave to the person who took over. I understood the value of my Someday/Maybe lists for myself, but I never considered they could be useful for others.

Turn the lights off when you leave

As the last action on my last day, I marked any remaining work-projects as either dropped or completed; and marked the Work folder, Work Someday/Maybe list and the single-actions Work project as dropped. It's both satisfying and a little sad to see a large part of your life dropping away like that. Like storing a massive ancient tome in a great archive.

Areas to improve

The point of GTD is not to be productive but rather to be stress-free, so I use my anxiety level as a measure for how much planning/reviewing I need to do. During this time, I was a little anxious about making sure I've captured everything at work, so an extra midweek Weekly Review would have put my mind at ease.

During this time I also noted an increase in what I call BTW tasks. You're having a conversation with somebody and they come up with "By the way, can you...". Nothing fell through the cracks this time, but it simply highlights the need for an always-on capture device.

GTD and OmniFocus did well here, I closed down all the projects, finished some Someday/Maybes, and passed many next actions to those tasking over as a little goodbye present. It was a fun and relaxed experience, rather than stressful.

My work wasn't done though, I still had a week to clear the apartment, close utility accounts, and pack to leave. Next time I'll go over what worked and what didn't when leaving the apartment.

Have a great one. See you next time.

-- Jay Blanco


  1. One should always document as they go along, and there was a lot of documentation in place already but the nature of the work means that documentation is the last thing to get done.
  2. Carl is not a real person, I don't know anybody called Carl. Except for Carl Sagan, he's awesome.