Getting Things Done on the road, part one

Before we started this blog, Coleman spent five years traveling every week for work and I had never traveled for work, but knew quite a lot about health and productivity thanks to my personal optimization and past life as CEO of a (now-mostly-defunct) coaching company. That lead to a pretty clear division of labor: I wrote about general health and productivity topics, and Coleman wrote about travel-specific topics and the application of general health and productivity to the travel lifestyle.

That division of labor is about to get blurrier —in a couple weeks, I’ll be starting a gig that will have me on the road roughly 45 weeks per year. I’m excited about the job, and even more excited about the opportunity it’s going to create for the work we do here.

For a long time, I refrained from giving advice about travel-specific topics for ethical reasons¹With the notable exception of this article about lifting weights on the road, which a) I got a lot of feedback from Coleman on and b) I judged as probably fine because it does little in the way of making recommendations; it mostly just lays out the options and provides some criteria for deciding between them. — but once I’m also traveling for work, all of those qualms about giving advice I can’t follow disappear and you’ll have two certified fitness professionals²I hold an ACSM-CPT; Coleman holds a CSCS. Both of us are obsessive hobbyist reader/researchers and self-experimenters

digging into the big picture strategy and tactical minutia of traveling for work.

As I prepared for this lifestyle shift, I realized my biggest question had very little to do with the ‘health’ side of business travel and much more to do with the ‘productivity’ side.

In various on-and-off ways for a number of years, I’ve used David Allen’s Getting Things Done as a model for organizing my tasks and my life. Unfortunately, the book lays a deeply paper-based system (that I’ve personally taken to), and provides few clues for implementing GTD when on the road.³Which I actually find rather surprising, given how often David Allen used to travel for seminars. To be clear, when I say few, I mean few: as far as I can tell, this the full extent of his advice for business travelers:

“If you move around much, as a business traveler or just as a person with a mobile life-style [sic], you’ll also want to set up an efficiently organized micro-office-in-transit. More than likely this will consist of a briefcase, pack, or satchel with appropriate folders and portable workstation supplies.”

Thanks, David.⁴I am reminded of this cartoon.

Placeless productivity

Thankfully, I’ve been been working from some form of GTD and thinking about the nature of knowledge work and attention for long enough that I can already see how my current productivity system will break down while traveling:

1. I rely heavily on having a dedicated desk where I sit and do work.
   This isn’t so much an issue from a GTD perspective but rather from a deep work and mindset perspective, but it’s still worth noting.
2. I prefer physical media: I like paper books and printing out things for reading, and I keep a lot of ideas in physical notebooks and as marginalia.
   This is going to get problematic for two reasons: one, I currently carry three or four books and a notebook in my bag at any given time. That’s fine when I’m mostly just walking ten minutes to a coffee shop, but when I’m flying every week, it’s not going to be as tenable. More importantly, those notes in notebooks and in the margins of books won’t be accessible to me when I’m 300 miles away — and that reference information is only valuable to me if I’m actually able to access it and use it when I need it.
3. I often default to capturing tasks and other stray thoughts on notecards or in notepads and throwing them into my physical inbox for later processing.
   This makes things difficult both from a volume perspective (there’s only so much space in a file folder) and from a lost information perspective (it’s very unlikely that I lose a notecard in the process of it going going from my desk to my inbox; there’s a much better chance that things disappear when they’re being thrown in the bottom of a bag and being dragged all around creation.
4. While I’ve experimented with digital task managers in the past, I often end up defaulting back to a written notebook listing projects and next actions.
   While one physical notebook isn’t much of a burden to carry around, I’m much more worried about having everything in one notebook and then leaving that notebook in a seatback pocket or the back of a cab. The concern here is partially suitability — I can’t seem to build the habit of using a digital task manager⁵Although being forced to may have a pleasant way of making that less true in the future. — but also redundancy and recoverability. When things mostly just live on my desk, it’s hard to lose them; when I’m traveling, it’s much easier.
5. I also do my daily time-blocking on note cards that I carry around inside of my work notebook.⁶These Levenger Dot Grid cards are the best note cards ever made.
   Same issues as above.

I don’t have solutions to these problems yet. I suspect I won’t until I actually try (and mess up) a number of ideas but some of those ideas are beginning to form. The main issues center around losing materials, not having access to them when I need them, and the physical burden of paper— so a good system (for me, maybe not for you) will allow for complete redundancy and accessibility, without losing the flexibility and customizability of a paper notebook.

This means I need to be able to access, manipulate, and use everything I need, anywhere, at any time, which requires tools with cross-platform compatibility and cloud storage that are highly customizable to allow for idiosyncratic workflows.

Experiment one

In a practical sense, what I’m talking about is a need for new buckets. In Getting Things Done, David Allen recommends six-ish buckets for stuff, with distinct kinds of stuff in each: reference, projects, project plans, someday/maybe, next actions, plus an “inbox” of some kind and a calendar. Some of those buckets hold lists of short, to-do type items, others longer freeform documents.

I’m going to try out a combination Omnifocus for lists, and Google Docs/PDFs stored in Google Drive for longer & more freeform documents. The harder part of this experiment is setting an objective success criteria — so much of productivity is about creating a subjective feeling of wellbeing. For now, I think the best way to approach this is to just see if these systems are maintainable. If I can use them and not fall back to paper-based systems and continue to keep them current and up to date, we’ll call that a success. (I generally think people obsess too much over productivity tools and use trying new ones as an advance form of procrastination. Find something that works well enough and satisfice.)

I’m going to spend the next couple weeks getting things set up and building the habit, and then the few weeks after that testing them out in a travel setting. Expect an update soon once I figure out what works best.