Planning For 2019

And so a new year begins.

The start of a new year is always an interesting experience. On the one hand, you’re in holiday mode; the previous week or four have often been spent celebrating with family, friends, colleagues and others. On the other hand, you’re on the verge of a whole new trip around the sun. You’re looking forward in anticipation for what comes next—at least, most of us are. Some people are making resolutions. Virtually everyone is giving some thought to their hopes and plans for the new year.

It’s also the time when those with a fetish for office supplies desperately begin to crave buying a new planner. Some—you know who you are—buy multiple.

In short, the start of the year is a time of focus, of contemplation and of planning for the year to come.

I’ve been doing my fair share of contemplation and reflection. A couple of weeks ago, I ruminated on the year just past. I also spent some time reviewing the most popular posts on this site. And over the last week, I’ve begun to think about the year to come. I’ve also started to plan what that looks like. And, to the point of today’s column, I have been considering the tools and approaches I take to manage my plans.

Like many others, I leave a trail of different planners, time management systems and organizational strategies in my wake. I have tried many, and I have stuck with few. Sometimes, that’s because the system itself is flawed—it is too simplistic, or it is too complex. More typically, though, my failure to embrace varying organizational approaches is a product of inconsistencies in focus, commitment, discipline and follow-through. Which is a nice way of saying that I get distracted and lose interest.

This is a relatively tough challenge to surmount. Not that it can’t be addressed and managed, mind you. But whatever organizational strategy you employ is only going to be useful if you actually use it. It doesn’t matter how good a system is if you don’t apply it. For that matter, it doesn’t matter how bad the system is, either—although then you might feel justified in abandoning it. Bottom line, if you’re not going to do the work, any system will do. And if you are not going to use the system you adopt, then it’s arguably pointless even adopting one.

Not that this has in any way stopped me from trying to find an method that really does work for me. Finding something that is effective has meant figuring out an approach that I can sustain, and one that makes a difference in terms of tracking, managing and maintaining commitments. In past writing, I’ve mentioned some of the influences that I’ve drawn on.

David Allen’s Getting Things Done was a book that I came across more than a few years ago now, and whose concepts have stuck with me. I’ve discussed it on several occasions here, in a variety of previous articles. The idea of a project as anything involving more than one step (as opposed to more traditional definitions) has been a helpful one. The use of contexts to organize by, tagging to-do’s with flags of “at work,” “at home,” “online,” or “when I’m tired.” The overall philosophy of having a single, trusted system was a critical insight; that without it, our brains continue to work at trying to remember all of the things all of the time.

Another resource has been Ryder Carroll’s Bullet Journal Method. I’ve linked to numerous articles about it previously, and found some of the ideas and concepts incredibly appealing. What I particularly valued was that you don’t need a ‘system’ per se. You just need a notebook. One, single notebook that contains everything. Have a new topic? Start a new page. Run out of space on this item? Find the next blank page and keep going. Flexible, simple, comprehensible and no fancy books or resources required (which hasn’t stopped bullet journalling from turning into a thriving and design-oriented pursuit for many).

Previously, I’ve organized my life through a combination of electronic software and on old-fashioned paper. This, if I’m honest, has been a big part of the problem. I use multiple devices, including several computers, a phone and a tablet. I need my calendar available and up-to-date wherever I’m working. So I’ve endeavoured to have all of my other planning information electronically stored as well. The system I’ve found most useful of late (given that I work in a Mac-centric eco-system) is a software product called Daylite. I’ve used it for about four years now, and that’s an impressive track record in itself.

Daylite integrates a number of essential components in one single place. It maintains records of all my contacts. It manages to-dos. It has integrated calendaring. It ties into the Mac’s email program. And it actually allows for managing of opportunities and projects in a way that—for the most part—makes sense for me. It syncs across all of my devices, and basically works like a stand-alone customer relationship management system (in fact, it’s designed to be a CRM solution to support multiple people collaborating together; I just don’t happen to use it that way).

All of that sounds great. Certainly, on the face of it, all of my information requirements are met. The challenge with that is that I don’t tend to have any of my technology in meetings. It’s there, certainly, in that it’s in the room with me. But unless I’m presenting from my laptop, I don’t have it open in front of me. I try to avoid looking at my phone. My tablet usually stays in my briefcase. My focus in meetings is on the people that I’m communicating with. I try to give them my undivided attention. This means that when an action item comes up, it’s not going into technology. It’s getting written down in my journal instead.

It’s this intersection between paper and technology that has proven the most difficult thing to work with in landing on an organizational approach that works for me. Note-taking notwithstanding, my previous bias was to try to get everything into software. And that’s where things fell down, because I never managed a sustainable habit of capturing all of the day’s notes online so that they were available. Sometimes it happened, but more often it didn’t.

This has frequently meant was that I might be trying to catch up on days worth of notes at a given time, capturing and entering them and organizing them. If that sounds painful and boring, it generally was. Often, my organization system was in some weird limbo between software and notebook. I didn’t have one trusted system; I had multiple possible sources of information, none of which were typically in sync with the others.

A couple of years ago, I recognized that I was looking at this situation backwards. What was occasionally available was software; what was constantly present was my notebook. And that’s when I gradually began to move back to a paper notebook as my primary planning system. If something needs to happen, it’s written in my notebook. Anything anywhere else is a temporary storage place until it gets written down.

Over the last couple of years, I’ve evolved how I use my notebook as I’ve adopted different techniques that work and don’t work. The one I’ve evolved is a mash-up of traditional project management and tools that draw from a variety of sources, but particularly Getting Things Done and the Bullet Journal Method. I don’t use any specific system. I’ve adapted ideas from a number of different places, based on what’s appropriate for how I manage and think about my commitments.

As we start 2019, I’ve found myself setting up a new notebook. That’s a bit of a coincidence; I’m not actually particular about starting each year with a clean book. I use a notebook until it’s full, and then I start a new one. I just happened to come to the end of a notebook as December approached. With time to unwind and reflect, I decided it was a useful opportunity to review my notebook structure, and to revise it appropriately.

My journal structure leverages several ideas that originated on the Bullet Journal site, and particularly some of the blog posts of how other people have adopted and adapted existing approaches and developed new journal tools and techniques. (A long trip down the internet rabbit-hole awaits anyone searching for #bulletjournal on Instagram).

I’ve outlined my overall journal approach—with acknowledgements of source of inspiration where appropriate—below:

• Indexing. I’ve only recently started to really employ indexes in my journal. While it’s a big component of the Bullet Journal system, it’s not one that I have previously embraced. Mostly because it involves maintaining a level of discipline in updating references. I’ve instead generally relied upon my journal being in something like chronological order, and skipped back and forth as needed when looking for information. Several challenges in finding specific details this fall, though, has finally convinced me that there is some value in taking the time to build references to where information can be found. A big inspiration for me is the “Calendex” proposed by Eddy Hope. I use this in two ways: relevant page numbers are circled if I have built meeting planners ahead of time for a particular date, and otherwise I reference the page numbers for all the notes that occurred on that day.
• Monthly Log. In order to try to keep track of my longer term commitments, I’ve got a number of pages that I use to keep a higher level view of my work and personal plans. I set monthly intentions for a number of key areas (inspired by @honeyrozes) and track how I do on those on a monthly basis. As well, I have a high-level snapshot of my month that identifies overall work and personal commitments, as well as what city I have to be in on a given day. I collect a list of to-dos for the month that I use as a collection point (until they get migrated to the week they will be done in). And I’ve built a habit tracker (inspired by @mightierthan and others).
• Weekly Log. The weekly log for me is the core of how I manage. I have a two-page spread of weekly commitments, identifying to-dos and action items that are committed to be done on a certain date. I’ve also started building lists for things I’m waiting on from others (inspired by @bujo.auslife) and a braindump of other action items that need to get done—now or in the future—but aren’t associated with a particular date (inspired by @mightierthan).
• Time Tracking. One of the challenges of being a consultant is that most of my revenue is based upon the actual time that I work. That means that—for the last 30-ish years of my life—I’ve tracked the majority of my waking hours in 15 minute increments. And while I use a timesheet package (BillingsPro , if you’re curious) I again tend to track time on paper first, and then enter it into the software. While that might sound redundant, I’ve found it faster and more accurate in the long run. I’ve leveraged the same structure for my weekly log to create a two-page spread of time entries.

Overall, that’s my structure. Every journal has an index up front (that I separate by projects, collections and an index of where monthly and weekly spreads appear in the notebook). Every month has four structured pages of planning information (intentions, high-level work and personal commitments, to-do collection and habit tracker). And every week has three two-page spreads (my weekly log, my brain-dump and waiting on items, and my time reporting). What appears between those is the records of each day: notes from meetings or from what I’m reading, or outlines and plans of work that I’ve got underway.

As I’ve noted, all of the above is a work in progress. It’s what works for me now (after a lifetime of trying to get organized) and I’m pleased to report that I do actually maintain it most of the time (and doing so has meant most commitments get met, expectations get managed and very little at this point falls through the cracks). That’s not to say that it won’t change in the future, of course. But my planner is a work in progress—just like I am.