This is my first set of monthly goals for 2020.

When I think about what’s blocking me from achieving more of my goals, the most immediately obvious answer is that I just don’t have a good system in place for allocating time and energy outside of my normal recurring obligations. I have a schedule, and anything outside of that schedule is “relaxation time”. In order to achieve any of the things I want to achieve in 2020, I’ll need significant amounts of time and energy where I can be productive, while being flexible on what exactly I’ll be working on during that time. This is my main theme for January: setting up a productive space to use in future months.

On top of this, it seems that any habit or goal is most fragile in the first few weeks, making January a particularly critical time. This whole project could fall apart unless I set achievable goals and craft structures to make adhering to them as likely as possible.

With that in mind, I have selected a few goals for January. It was actually tricky just to spend adequate amounts of time thinking through what I wanted the goals to be and planning out how to maximize success likelihood. I ended up relying on New Year’s enthusiasm and sacrificing some other scheduled work, which is not sustainable. In the future I expect to use the time set aside by my January habits to craft the goals for subsequent months.

I would also like to improve my ability to make predictions about my likelihood of following through on various types of goals with various structures, in order to better plan around potential roadblocks. Towards that end I’ll be making probabilistic predictions about these goals, and rating them at the end of the month. Whenver there is a parenthetical probability - such as (60%) - that means I am assigning 60% probability on the previous prediction being correct. Doing this has also helped me identify where my goals are weakest, such that I can focus on getting better structures to support them.

Without further ado, my first set of monthly goals:

Goal 1: Accountability

My first goal for the month is setting up a consistent accountability structure. This has two parts: a one-time setup process to make sure I have accountability in January, and a recurring process to carry forward into future months.

In order to actually succeed with these goals, I need to do some pre-month work. This includes taking a step back, thinking through my life, and selecting goals for this first pivotal month. It also includes setting up systems to support me in actually following through. On January 2nd I decided I needed to invest significant time into figuring out what these goals were and writing them out. Then I’d need to find a “challenge network” of 2+ people who are actually capable of holding me to a high standard, and get them to agree to read through the document and hold me to it. If you are reading this now, you can probably guess how that went (and I am extremely grateful to those who agreed to fulfill this role for me).

The recurring structure I want to build to support future months is an extension of the one above. Each month I will spend some time thinking of appropriate goals for the coming month, write them out, and send them to my challenge network. In addition, I will write these up as a public blog post (hello, self-reference!) and follow up with a retrospective at the end of the month. This retrospective will take a look at what went right and wrong over that month and clarify my learnings.

As an interesting aside, I initially assigned 95% probability to getting the pre-month work done on January 2nd. It turned out to be much more work than I was anticipating, and didn’t fit into the time I had allotted. However, because I had assigned such an aggressive probability I felt more inclinded to spend extra effort making sure it happened. If I had instead estimated a 50% chance of success, I think my actual likelihood of finishing would be closer to 50%. This means there is a feedback loop from the probability I estimate to the final outcome, where higher probabilities increased the actual likelihood of success. I expect this to only be true if I actually believed the estimate when I made it (so I can’t game this by assinging 99% to everything). I’m not entirely sure what to do with this information, but for now I’ll keep an eye on it. If it seems like a range of probability estimates that would be “correct” (such that my actual odds of success match whatever number I choose to give in that range) I’ll just pick the most favorable number in that range.

Note that this goal is time-negative. Adhering to it requires spending productive time and energy, and that has to come from somewhere. I’m not currently very good about allocating these kinds of resources, but the following 2 goals attempt to set up this kind of productive space. If at least one of the below goals is achieved, then my estimated likelihood of successfully sketching out a January retrospective and coming up with February goals is 80%. I consider this the “minimal” set of criteria for bringing forward a recurring accountability structure. My estimate for completing the “full” set of criteria in this goal is 50%, mostly just out of the possibility that I decide to actually write and publish January posts in February. This wouldn’t be that big a failure (if I actually do them). I’m treating the non-minimal criteria as lower priority than everything else in my January goals.

Goal 2: Weekend Space

I currently struggle with being productive at home, as this is historically my “relaxation spot”. This is especially true on weekends. In January I want to spend at least 2 hours each of the 4 weekends in a productive headspace at a local library. Other than that, I can spend the time doing whatever I feel like in the moment.

There are some high-priority tasks on my plate that I will probably feel some amount of pressure to do, but for now I will always maintain the option of just ignoring those and doing something that feels more pleasant. My main concern this month is just setting up adherence and getting the ball rolling, so I’ll avoid anything that would decrease my likelihood of sticking with this - such as enforcing unpleasant tasks. Fortunately none of these has to be completed by the end of January. The only task I’d like to actually ensure I’m scheduling is the writing of blog posts needed to complete Goal 1.

I have scheduled calendar events for this time, and if something comes up that conflicts with the schedule, I will successfully reschedule to a different time and go anyways (80%). There should not be any full-weekend events or excessively last-minute priority schedules in January that I can’t work around (90%). If I arrive to the library later than scheduled, I will just shift back my plans so that I am spending at least 2 hours there (95%+).

I have a pretty strong intuitive notion of what a “productive headspace” is, so I don’t expect that to be something I am likely to game (95%+). I expect that I will spend most of my time in ways that I wouldn’t predict ahead of time (65%).

If the pre-month component of Goal 1 is completed and I have an accountability structure in place, then I assign around 70% likelihood that I successfully spend the appropriate time over all weekends. 75% if I can get someone to join me on the first trip to the library. Much of the lost probability is just due to overall uncertainty since this is the first time I’m doing something like this. I’d roughly estimate 10% chance that some scheduling thing will come up that I can’t work around, 10% chance that something comes up that I could schedule around but use as an excuse not to go, and 10% chance that I come up with some other excuse in the moment for not going one of the weeks. Most of this is concentrated on the first weekend or two.

Goal 3: Weekday Space

Very much in line with the goal above, I want to clear some freeform productive space on weekdays. This means at least 45 minutes in a continuous block. 45 minutes is my standard pomodoro time and feels like a good unit of work. This does not apply to any “weird” days where I’m on an unusual schedule (if I’m sick, holidays, etc). It would be nice to still be productive on at least some of these days, but that feels like it should be beyond the scope of what I target this month.

I have two types of daily schedules, so I’d need to make this work in both. In the first schedule (which I’ll just call A) I expect it will be really easy to accomplish this as I’m already basically there (95%). On B schedule days I have a convenient time to do this, but it’s reliant on me remembering at the appropriate time that I am supposed to be doing this kind of “productive headspace”. My estimate of having at most one failure to use this time on B schedule days is 65%, and getting the number that high required investing some time in setting a TAP to remember this.

Most of the uncertainty is in the first couple times I’m on B schedule, or if there is ever a scenario where I have no B schedule days for a long continuous period of time. My answer to the latter point is just to make a very visible checklist in my room for days where I meet this goal, so that even on A days I’m still (hopefully) reinforcing the habit for B days.

Goal 4: Legacy/Running

I want to run a 5k at faster than 6-minute-mile pace.

This goal is in somewhat of a separate category from the ones above. Whereas those are intended to form a coherent foundation for future monthly-goal settings, this is an extention of an existing long-term goal that I’ve had for the past ~2 years. I’m including it here because it is something I want to invest effort into improving each month this year, and I can piggyback on this format. Besides, the whole point of these monthly goals is so that I can eventually achieve some object-level projects. Having an object-level goal running in parallel that doesn’t interfere with the other goals seems like a good way to keep things grounded.

The overall objective in this category is well-defined, but I expect it to take significantly longer than a month to achieve from where I am now (my fastest 5k was at 6:58 pace). I got injured again towards the end of December, so my specific goals for this month are around recovery and prevention of future injuries. Namely I want to work on incorporating strength training and cross training into my routine while slowly ramping mileage back up. The exact mileage will depend on how I’m feeling and whether I feel sufficiently recovered, but I hope to at least get back to 20mpw (miles per week) by the end of the month.

As for strength and cross training, I currently do rock climbing once a week. But this doesn’t feel sufficient. I want to do 3 days of strength-type training per week in January, so I’m adding one weekly group fitness class, and one day where I will do standard weight training at a gym.

For the group class, the primary reason I might not do it is if I forget to bring an extra set of workout clothes with me to work. I set a phone reminder to bring clothes those days, and will keep an extra backup set at work in case I forget. With these I expect 85% likelihood of doing the group class each week.

As for the weight-training day, I’ve just decided to replace my usual run that day with the strength training, and add a run to what used to be my rest day. My primary concern is that I won’t do this on B schedule days if I don’t go to the gym, but in this case I can just do bodyweight exercises at home. I only have 70% likelihood here, mostly because it wouldn’t be terribly surprising if I missed one B day. I’m much more confident that I will hit this at least 3 of the 4 weeks (90%).

Parting Thoughts

Based on the numbers I’ve given so far, the likelihood of achieving all of the non-legacy goals is ~30% (note that I’m assuming these are not independent events, since I think doing well in one area makes it more likely to do will in another and vice-versa). This honestly still feels like it might be too low, I might not be using high-enough conditional dependency assumptions. These are also fairly sensitive to the amount of social support I end up receiving for this initiative. But if I do end up doing better than these predict, I can be more confident in my ability to follow through in future months, especially as the accomplished goals themselves will give me time and struture to support more ambitious future work.

edit: you can find my retrospective for these goals here.