Hello, 2019

I’m being a bit more careful about defining goals this year. Certainly, there are some things that I’m aiming to do, or that I need to do, but these things have to be balanced against the universe not especially giving a damn about my wants and needs — and I need to be okay with that. But more importantly, I’m working harder on timeboxing my projects in OmniFocus, for a few reasons.

I’ve realized is that I’m happiest when I’m living a considered life. An examined life, in a sense, but without getting too mired in the details. I set a bunch of goals that I couldn’t (or didn’t really want to) meet last year, and I want to avoid that this year; I’ve learned the hard lesson that numbers measured and checkboxes ticked are worthless if they ignore the needs of who I want to be and how I feel, set in the context of what I’m capable of.

So I’ve spent a bit of time thinking about this. Who am I? What is my True North? Knowing these things, how do I make sure my bearing is correctly set to get there?

I learned some important things over the last year. I’m someone who needs focus time, and who needs to create things. I’m someone that needs real-life social interaction. I need a solid seven hours of sleep, and I also need quiet time to be alone with my thoughts. Despite not having touched an instrument in over a decade, I still consider myself a musician. So I’ve been working towards goals that meet these needs. Why then, are these projects mostly still sitting on the backburner?

I think it’s because of pattern of “overs”. Overenthusiasm leads to overcommitment leads to overwhelm, and so I need some way to rein in that enthusiasm; I need to be more deliberate about how I treat my waking hours. Maybe it isn’t a coincidence that a calendar resembles a chessboard; to carry the metaphor a little further, the way I’ve been using my time feels more like I’ve just been pushing pawns around willy-nilly, rather than playing strategic moves that get me to a win.

So, yeah. Being more deliberate with what I do means thinking more strategically about what I can do. I’ve come to realize that my actions broadly fall in one of two categories:

  1. The administrivia of everyday life: This includes the various one-off and/or recurring tasks that I can’t forget, like checking the fire extinguisher, doing dishes and laundry, and other things you’d find on single-action lists, as well as the meta-type projects that keep things on track, like doing a retrospective and planning session every week. I also include tracking lists like things to read, things to shop for, and so on in this category.

  2. Goal-focused projects: These are the bigger projects focused on a very specific outcome. Until now, these are things that I’ve been throwing into OmniFocus willy-nilly with aspirational intent, and that’s not been working for me. One major thing I’m addressing this year is setting a timeframe for projects. Not a due date, per se, but rather defining when I want to work on things. To that end, I’ve created a nested folder structure in OmniFocus into which I’ll arrange my projects:

📂 Administrivia
  📂 Meta/Maintenance
  📂 Single-Action Lists
  📂 Tracking Lists
📂 Projects
  📂 Someday/Maybe
  📂 Do this year
    📂 Do in H1
      📂 Do in Q1
        📂 Do in January
        📂 Do in February
        📂 Do in March
      📂 Do in Q2
        📂 Do in April
        📂 Do in May
        📂 Do in June
    📂 Do in H2
      📂 Do in Q3
        📂 Do in July
        📂 Do in August
        📂 Do in September
      📂 Do in Q4
        📂 Do in October
        📂 Do in November
        📂 Do in December
  📂 Do next year
  📂 Do in 3-5 years
  📂 Do in 5+ years

This makes more sense to me over trying to define stuff as Personal, Business, Hobbies, &cet. — after all, if it affects my life, it’s personal. Rather, this gives me a better visual representation of how much I’m packing into any given period of time. It’s fine to punt from one period to another, but the key is to recognize that I only have so much time available to do things; unless “the move makes sense on the chessboard,” if you will, it remains an idea in my Someday/Maybe list, which can act as kind of a project backlog.

Projects will be added to the appropriate folder depending on how long I expect it will take to do it; in other words, if I think I can get a project done in a month, I’ll add it to a month folder (e.g., Do in February). If it’ll take three months or less, I’ll add it to the appropriate quarter (e.g., Do in Q2). Six months or less, and the project goes in the appropriate half (e.g., Do in H2). And anything that I expect will take the entire year will go in Do this year.

This also gives me a better way to track progress against short-term (current/next year), medium-term (3-5 years), and long-term (5+ years) goals. So, if we have a goal of, say, visiting Japan in 2021, I’ll add that project to the Do in 3-5 years folder, and as time moves forward I can see how I’m progressing during my weekly reviews; eventually this project will be moved to the Do next year folder, and then somewhere in Do this year.

I’ll revisit how this is going for me every quarter, what changes I may have made, and what I’ve noticed, but I’m already feeling happy with how many stale projects have been dumping back into my Someday/Maybe list, how many were dropped, and the outline of the year that’s beginning to unfold before my eyes.

More tk.

Angelo Stavrow

Montreal, Canada
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Tinkerer with a strong interest for development, of both the personal and software persuasion; easily defeated with spatulas. Equal measures enthusiasm and concern for tech's effect on the world. He/him.