Leveling Up Skill #3: Tracking our Progress with Accountability Calendars

Reading Time: 11 minutes

This post is part of a blog series called Leveling Up: A Guide for Programmers. The series covers skills you can use to learn faster, more easily, and more strategically as a programmer.

In the previous post we talked about removing reliance on motivation to make progress on your project. That post introduces about a framework for discipline-oriented practice to help you build habits, so you can rely less on feeling like practicing. One of the items in the framework mentions an accountability calendar. That post doesn’t go into detail on accountability calendars: this one does.

So, what is an accountability calendar, and why is it useful? Let’s look at an example calendar, so you have a picture in your head.

An Example Accountability Calendar

I like to keep an accountability calendar for each ongoing learning project. They look something like this:

Accountability Calendar

Across the top, we have the days of the week (‘R’ represents Thursday: this is a holdover from the way my university represented that weekday on course schedules). This calendar tracked nine weeks’ worth of independent study for me, and the version you’re seeing shows what the calendar looked like at three and a half weeks.

Each day, after my work session (or lack thereof), I track some key details about the session in this calendar.

You’ll notice some shapes, numbers, and symbols inside many of the day boxes for the first three and a half weeks of my calendar. Let’s go over what they mean.

 1.  Number in top left corner of box: this is the date.

 2. Number in the bottom left corner of the box: this is an estimate of the complexity of work that I completed in my study session.

  • Zero: I did nothing today. 
  • One: I did something today that I pretty much knew how to do before I did it. Examples:
    • I wrote a piece of my learning app that was very similar to something I have written in the past.
    • I read a chapter in a book and took notes on the chapter.
  • Two: I did something today that I only partly knew how to do before I did it. Examples:
    • I wrote a piece of my learning app that I had to consult some blog posts or book chapters in order to do.
    • I tested out a couple of different approaches to doing something so I could choose one approach.
  • Three: I did something today that I had no idea how to do before I did it. Examples:
    • I completed a piece of the app that required extensive research, weighing lots of different options, and/or constructing lots of different moving parts.
    • I implemented an approach discussed by an author I am reading that I had never heard of before I read this author.

Worth noting: the points don’t necessarily gauge time spend. I can spend three hours reading a chapter and copying terms, but not really make any new connections and end up with a 1. Or I have no idea how to do something, do some research, learn a brand-new thing about my framework’s capabilities that allows me to do the thing I want with a tiny change, make the change, and rack up a 3-pointer from less than an hour of work.

That case with the fast 3 is rare for me. My points do tend to correlate with time spend. But if they don’t for you, that is totally OK and normal. I also don’t worry too much about getting these estimates perfect. They’re deliberately rough (just 1-3, not more numbers) so I don’t start representing complexity with a misleading level of specificity. I only have them in there to help me gauge what I worked on when I look back over my calendar later.

 3. A square (see the first, the 13th, or the 16th) or a star (see the 8th, 11th, 18th, and 22nd) next to the date number: I put the square on days when I was feeling especially motivated for my independent study. I put the star on days when I was feeling especially not motivated for my independent study.

I find it helpful to remember how I was feeling on a given study day for a couple of reasons:

1. I can look back and notice whether the complexity of the work I do correlates with how I was feeling going into the study session (for me, it usually doesn’t).

2. I can track patterns in how my attitude toward independent study changes over time. For example, do I hate studying on Mondays, or feel especially de-motivated the day after I get zero points? If I have a bunch and then start to have fewer of them, I can ask: what has me so motivated? Can I keep doing that? If I start to have more days like this, what’s wrong? Am I feeling stuck? Am I not enjoying my project? Are my goals too ambitious and getting me discouraged, or are they too timid and leaving me bored? These trends can clue me in to opportunities to change my system in ways that work better for me.

There’s another type of pattern worth talking about: routine. Lots of things affect how we feel day to day: sleep, hydration, diet, exercise, medicine schedule, life events, work stuff, family stuff. I don’t have those things in this calendar I’ve shown you. That’s because I happen to keep them in other calendars (I have a training journal and a keep-my-commitments-straight calendar that I can cross-reference to get this info).

I don’t recommend you start calendaring with three separate calendars. Instead, if this is your very first calendar, you might consider adding that info to this calendar. Draw a little fork for days when you ate pretty healthy and a little spoon for days when you ate…not so healthy. Add a little running stick figure for your exercise days, and a little pillow for days when you got good sleep (or a round eyeball for days when you’ve had poor sleep). Add a little Rx symbol on the days when you take your medicine. You don’t have to judge yourself day to day on how “well” you did on all these things (I eat cake, like, every day. It’s terrible. I don’t stop). Instead, we’re just tracking this info for the sole purpose of looking back and seeing how it correlates with our attitude about independent study. That information can help us slowly move toward routines that help us feel better about the studying, on average.

I can look back and remind myself of all the points I got on days when I didn’t feel like studying (star). I add them up and figure out what percentage of my total points they make. Over time, I do about 20% of my points on days when I do not want to work on my independent study. It’s helpful for me to remember that: if I do the work even when I don’t feel like it, I end up 20% ahead of where I’d be if I only did it on days when I wanted to. That means, after four weeks, I’m a full week ahead of where I’d otherwise be. That’s a meaningful difference.

One more thing on stars and squares before we move on: I happen to only record stars and squares on days when I do studyThat’s not scientific: it happens purely because I open my accountability calendar at the end of study sessions, so if I didn’t study, I don’t open it. (The zeros I add in later when I see blank squares from not opening the calendar on non-study days). Also, I feel like I only should get a star if I did something in spite of not feeling like doing something. Again, this is my system. Do what works for you!

 4. A circle (see the 6th, 11th, and 19th) next to the date, or next to the star/square: I put the circle on days when I make a breakthrough. I learn something that helps me think about a topic in a whole new way, or I come to understand a concept that I have struggled with. The arrow from the circle points to a very short description of what I had a breakthrough about.

The circles don’t correlate with points, exactly: I could be reading a chapter, get a breakthrough while reading that chapter, and still log a 1 for the day. (Then maybe another day I apply that breakthrough to code and get a 2 or 3! But not always.) I still log the breakthroughs because I like to look at days when I have a star and a circle to remind myself that learning still happens on the days when I don’t feel motivated. The breakthroughs also usually represent memorable moments that I can look back on a year from now and thing Awww, I remember when I didn’t know that. I’ve come so far!

This calendar thing seems super complicated, Chelsea. Why should I do this?

First of all, maybe you shouldn’t. Different things work for different people. If you just read this whole post like ‘this seems ridiculous, why would I care,’ then this particular tactic might not be the one for you. That’s okay: skip it! It’s your skill development, and you should do what’s going to work for you. 

Here is why accountability calendars work for me: I love to track things and congratulate myself. In kindergarten, they give us gold stars and stickers for doing stuff well. Then we get to adulthood, and people don’t give us gold stars anymore. But on my calendar, I can give myself gold stars. In fact, my most recent calendars include actual gold star stickers that I got at Office Depot. There’s no shame in it! Give yourself some gold stars! (If you cannot be seen purchasing stickers for some reason, email me—chelsea at chelseatroy dot com—and I will send you some stars).

I also love to track my progress on things because, over a long time, I get to see my progress. This entire blog exists because I wanted to track my skill development as a programmer. When I look back on my posts from years ago, I see a meaningful difference from what I write now. That’s encouraging! It means I’m getting somewhere! The same thing goes for accountability calendars: on days when I get down on myself and feel like I’m not learning, I look back at the breakthroughs on my calendar from a month ago. Inevitably there are things on there that I now consider ‘obvious.’ That means I’m learning. The calendar helps me look beyond my mood to get a more encouraging picture of the work I’m doing.

Also, the calendar you see above looks more cryptic than yours will. Years of iteration have brought me to the format you see here, which stores a lot of details that are important to me with a very small time investment for noting them down. I have weird shorthand and odd symbols that I have come up with to slash time and effort from my calendar-keeping. If you are writing your very first accountability calendar, yours might have more detail and look more like a “traditional” calendar.

Finally, even if you’re lukewarm the idea of the calendar, I encourage you to give it a try. Maybe you’ll make some changes that work for you and find that you love it! Maybe, after a month, it will seem superfluous, and you’ll stop doing it. That’s OK. The process of teaching yourself something includes a lot of trial and error to figure out what will work for you. You can try techniques and then move on.


Accountability calendars give you a way to track your work on your independent study. You can record how much work you do, what kind of work you do, and whether you felt like working. Over time, the calendar gives you a picture of the progress you’re making and allows you to identify patterns, like when you enjoy working the most or the least.

You don’t have to do a calendar, and it might not work for you, but it can be a helpful way to get a long-term view of you progress. Even if it doesn’t sound like your thing, it may be worth your while to give it a try.

If you liked this post, you might also like:

Advanced Pair Programming: Learning From Your Pair

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One comment

  1. Thank you! I’m in a place of uncertainty of what I want to do with my career at the moment and your advice has been invaluable for keeping myself on track.

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