Habits and habit tracking

19 min read

Switch from goal-based approaches for what you want to accomplish to figuring out how to create habits and systems. Goals fade, habits compound.

When I look back over goals I've set myself over multiple years, what sticks has been the ones where I've been able to set up regular, disciplined habits and/or systems that have managed to contribute to their achievement.

This past year, especially, I've managed to do more of what I wanted to set out to do, and what I told myself were priorities at the start of the year, than I have in previous years. A lot of that has been about embracing habits and systems, rather than beating myself up on merely setting goals.

While the body of literature on this is massive, and ranges all the way from figuring out how to re-wire your "grit" (nb: the marshmallow test experimental result has been overturned), "willpower muscle" fatigue, and a slew of other opinions on your personal failures, setting up habits and systems are a surefire way to de-risk you achieving what you want.

True life change is actually quite hard. Inertia is one of the foundational forces of the universe and things like you and me like to keep doing what they're already doing unless acted on by outside (or internal) forces. Real changes require massive effort to overcome that inertia, unless you start small and slow and compound over time.

Setting Goals

Part of that is about setting goals in the first place that getting to the heart of what you really want to accomplish.

I feel one of the problems people often make is to set goals as a proxy for what they actually want. True transformative and satisfying life goals are actually about changing what you are, not what you've done. And figuring that out is more about what you want to be, than what you want to achieve and understanding, at the very base level of the thing, why you want that goal.

For example, do you really want to run a marathon? OIr do you really want to be able to think of yourself in your heart of hearts, as a runner? Do you really want to eat less junk food, or do you want to think of yourself as someone who is healthy and feels great and looks good? Do you really want to write the great Canadian novel or do you want to think of yourself as a writer? Do you really want to prioritize your career, or is what you're actually after financial stability? We are what we do continually, so many goals are really about transforming into what we want to become or think of ourselves as.

I can hear you saying, why does that make a difference? I'd argue goals are guideposts, or indications that you can claim you are one thing or the other, but habits and systems create the basis of what you really want to be. And that is really the point of goals. How do you transform from who you currently are into the person you want to be.

So, the first thing you need to do is to think about the goals you do have in the back of your mind, and figure out what some of them may be an actual proxy for. For most people, most of the goals they have are more an indicator of the deeper thing they want to be. And I think that's the key thing people need to look at and think about in terms of setting themselves up for success.

The transform trick - Actual Goals vs Signposts

If you do have a list of goals that are in a semi-SMART form, take them, think of them as "accomplishing this would indicate that I am or I have become... " and think really hard about what that would actually mean about you accomplishing it. What does it say about you or your wants and desires? As an example when I broke my own ones down into things I truly cared about and made me happy, I found the following things were actually what I wanted to be able to say about myself.

I am...

  1. An adventurer and traveller
  2. Healthy and very fit (really, to support being able to do the above)
  3. I am a writer and teller of a good tale well told
  4. I am a wise counsellor, giver of good advice, and maker of good decisions
  5. I am a good friend and partner
  6. I know how the things in the world work and am very knowledgeable
  7. I am not someone who worries about money and I have enough to do what I want

You could probably even break these own even more to talk about how I want to be heard, or influence, or be valued, or even desired, but in a sense these were helpful for me to understand the things I actually gave a crap about (versus say, having a shiny car or a big house or wanting to look fashionable.).

Take those and develop a habit over each

So, take those true goals (let's call them) and put the indicators you've probably got grouped and then think about how often you'd need to actual exhibit as a habitual demonstration, that you were actually these things. For me, this was a matter of figuring out what I could do daily (I really recommend thinking about how often every week or say every x days), weekly, monthly, quarterly or annually. Or, how many times within any of those periods.

For example, for me... and I've heard this from just about every writer worth their salt... you have to write every day. Show up and write is one of the mantras every successful writer seems to recite. So, we can put that one down as a Daily... though to be fair to myself, and recognizing that I will often fall off the wagon, I give myself an every 2 days modifier so I can see myself as having a solid writing session at least three times a week (as it happens, I now try to write every morning right after I shower, get ready, and sit down at my writing desk with coffee (as I am doing right now as I write these words.).

Make sure you have time to do the things - set a place and a time

Don't do too much. And try not to do everything at once (with apologies to Michael Pollen.).

It is tempting, once you have a better view of what you want to be, and the habits to define that, that you try a major life overhaul. First off, I'd advise you figure out how much time each habit will take in terms of a time budget each week (day/month) and then figuring out if you actually have time to do all the things you want to. Hard trade offs and decisions may be required. Much like peoples' work lives, you don't want your habits to become yet another long laundry list of things you can't accomplish (strangely, I find hitting my habits every week actually makes me feel like I really have my crap together and don't suck at life.). I call this the New years Resolutions problem. Focus on a few key habits first, then layer on other ones as those habits form.

For me, key watershed habits revolved around making sure I had carved off time for them in my calendar and did not allow other things to interfere with them. For example, if I am going to get up every morning and write for an hour, I actually need a sufficient amount of time to do that before I need to run off to work and my busy day job. That means I have to get up by a certain time every day and, if I want to get sufficient sleep, means I have to go to bed at a certain time every day. So, first habits happened needing to be:

  1. Go to bed by midnight every night
  2. Get 7 hours of sleep a night

Now, you might think those are two dead easy ones, but they are amongst the ones I have the most difficult keeping. But, what has become very apparent after tracking my habits over some amount of time, when those fail consecutively , everything falls off the wagon (not just writing). So, I worked the first few week or so on just on making sure I was going to bed on time and getting a solid seven (embarrassingly, this did involve setting alarms to go to bed as well as get up.).

From there, getting up, showering, making some coffee, and having that on my desk in front of my trusty laptop so that I could peck at the keyboard was an easier step. Admittedly, the first few weeks it was not a full hour, nor did I completely resist distraction if it was a hard morning where the words would not flow, but even just sitting down at my desk and going through the motions was progress. Now, on weeks that are running smoothly I'm sitting here tapping away at the keyboard while sipping my coffee. It's become comforting. In fact, it feels subtly wrong if I am not doing this in the morning now.

Another example, for getting into a gym habit, the first week I just gave myself credit if I left work, went to the gym and just changed into my gym clothes even if I didn't do a full hour. Sad, yes... but in the end it's now pretty engrained as a habit for me.

What to Do When Things Go Off the Rails

My big challenge here is not so much now doing this, as making sure I am able to do it when I'm on the road or other "life events" make sticking to a regular schedule or similar more difficult.

For example, my job quite often has me in a certain foreign city where the traffic is terrible and the added time for commutes throws a number of things into chaos life-wise. I don't sleep as well in hotels in general, and getting to bed on time, getting up on time, and even getting to write in the morning before I need to make it to the office is a bit problematic since I need to add in a commute of very uncertain length on any given day.

To be honest, one of my biggest challenges, particularly since the weeklong trips sometimes get extended is figuring out how to keep healthy eating habits, sleep, writing, gym, and TIL from going off the rails while I am visiting the megapolis. There is definitely a close correlation between seeing my habit tracking go all to hell and being in said city. Not only that, falling off the wagon extends back here to home when I fly back and it seems to take me a day or so before I give myself a stern talking to, hit "reset", and get back on track. This is far from optimal.

It is easy to beat yourself up when things go off-script, get demoralized, and eventually give up. It is far better to frogive yourself, declare a reset, grin stoically, and get back to it.

Figure you're starting from scratch again and start back on the habits again and particularly, the tracking (which arguably is a habit as well.). While my current habit tracker does not support it, I also think it's powerful to merely mark a habit as skipped for a particular day or week if it would have been simply impossible for you to exercise it (say, being sick or injured, or some other life event hppens. As long as you're being honest with yourself that there were mitigating factors other thanm say netflix couch potatoing or bneing lazy.).

While some may say this is giving you an out, I really find what it does is let you understand why your habits may or may not be working as well as you'd like. So, for me, I find "skips" a good indicator of why something may or may not be working (for example, the number of times someone asking me on business trips for an end of day meeting at the last minute, and then me hitting megapolis traffic and getting very late back to where I can use the hotel or mall gym, seemed to be pretty legion on reflection of days where there are holes in my streaks consistency graphs. Now I set a double alarm to get out of the office, so even people asking me for "just 5 minutes" ends up being timeboxed.).

As some advice, it's most cathartic to pick up multiday or week or longer habits since the "Seinfeld method" of seeing your habit trails compounding and full over time goes quite a long way to not wanting to break the chain, so re-establishing that "full grid" is easiest if you pick off longer sequence habits first (say, once a week or fortnight ones), and then get back to dailies. Especially, if that method works for you, that's the best way to tackle getting back on track and re-establishing a good streaks schedule.

Craft a conducive environment

There were a small number of things I found really helped me in terms of encouraging good habits or discouraging bad habits. For example, it is well-documented, and quite amazing, how even very small cues in your environment can have large effects on your probability of habits happening or not happening.

For example,

  1. Always keeping a set of gym clothes in my knapsack and packed (even better, picking a gym that provides attire as an option even at extra cost) has gone a long way to ensuring I make it to the gym.
  2. Deleting all but one of the apps that I would use to order food delivery has made me much better at eating the healthier food options in my fridge (even if I have to prepare and cook the food) or stopping in at a much better class of restaurants where the food quality and healthiness is much higher.
  3. Getting rid of all the ice cream (a personal Waterloo) and other unhealthy things in the house
  4. Having a set grocery delivery from one of the grocery stores have gone a long, long way on the better eating a health front.
  5. Turning off Netflix's "Autoplay Next Episode" feature (believe it or not) made it vastly easier not to sit on the couch bingewatching all evening and instead do other things
  6. Even as small a thing as having my laptop set up at the desk and powered up for the morning so that it is ready to go when I sit down with my coffee the next day has paid dividends

All these small things add momentum to the fact a habit is going to happen. Crafting an environment that either makes it easier for good habits to happen, and more importantly, for bad ones not to happen goes a long way to inculcating those habits.

So, take an inventory of the habits you want to create or break and list just one thing you can do beside each one to make sure that you are more encouraged to have it happen or something to discourage it a little more. Admittedly, some of this requires some self-reflection on what may possibly be slightly unconscious habits, but the exercise is a good one.


I personally find habit tracking essential. Being honest with yourself means tracking. It is terrifying how your brain tricks you into thinking you've done more or less of a thing than you actually have. Even daily journalling was useful for tracking, but I kind of shocked myself when I went back and actually reviewed, versus my impressions, whether I'd actually been hitting habits like I believed.

So, I became a big convert to using a separate, simple habit tracker. Making things visible is also scarily conducive to ensuring you try to keep up the habits. There's a whack of trackers out there, particularly in the mobile space. I personally prefer one on my computer (for screen real estate to see patterns), rather than my phone and tend to go minimalist and for long-term portability rather than too fancy. I do think there are a few essential components and some nice to haves that make a good habit tracker, but your mileage may vary.

  1. A global "Seinfeld" Don't Break the Chain consistency graph (viewable for more than a week)
  2. Easily editable and amendable tracking (particularly for past days)
  3. Good habits being done and bad habits avoided
  4. Track by days

Some very nice to haves

  1. Supports Skips
  2. Portable/exportable data format
  3. Can track via semantic time ranges (eg. once per week versus once every 7 days etc)
  4. Warns when you're close to a habit threshold

After stumbling through a couple of mobile apps that purported to sort my habit tracking (Way of Life, and Streaks), butiPhone habit trackers, due to screen real estate and the realities of the phone, often allowed me to tick off when a habit happened in situ, but did not give me the diagnostic information or visualizations I needed to figure out why habits might be going off-track.

I started using the habits feature available in emacs, but abandoned it when I switched back for a while to Taskpaper. Also, strangely, it made my org-files feel quite crowded, the ability to edit files for mistakes or historical events was a pain, and it made me feel like I was conflating habits with my todo list. It is quite nice though, and may work for you, especially if you're already emacs-literate. For example, the consistency graph (aka Seinfeld graph) is good and also warns you when you are close to having a habit overdue (which has caught me once or twice in the habit tracker I switched to from emacs org-mode habits.).

I ended up settling quite happily on a minimalist command line tracker that I run in a tmux tab in my terminal called Habitctl. Like most CLI tools it ends up doing something small and well, and has the advantage of recording my habits as a super portable text file format (which is also very hiuman readable) for tracking over time (and also means I can edit them with a simple text editor when I realize I've screwed up or possibly even move to another tracker if something better comes along.). Sadly, the author has not been updating the software (I've been thinking of re-implementing it in something other than Rust and adding features like Skips and threshold warnings just to make my life easier.). The tracking is quite simple, but the main results is a nice consistency graph and sparklines for how your habits are going (small quality of life improvement, I run my terminal full screen on the Mac and on linux which makes this a nice keycombo away. iTerm2 and Guake on linux.).

Habitctl in action - not a great last two weeks though

The thing I like most about this is being able to see at a glance how you're tracking over a swath of time. Where I see too much bare patch in the graph I try to diagnose what happened and figure out how I can deal with similar situations in the future in an IFTTT sort of approach (If This happens Then That needs to be done to correct for it). That's been instructive on course correcting a bunch of things. Though I do notice one thing that is hard for me is giving myself a break when I fall off the 100% mark some of the time. I kind of celebrate when I am at 100% but beat myself up terribly when I fall below the threshold. To make everything sustainable at 100% of the time requires a lot of discpipline and I almost need a "push" (rather than skip for whatever reasons) feature where I can give myself credit if I am just a day or so over on a habit sometimes. Overall though, it's amazing how actually measuring things has kept me on track and improved my success rate on things. And of course, that skips feature for when things are simply impossible due to being on a trip, falling ill or injured, or due to things beyond your control needs to be in there or you start making yourself feel like you're making excuses. Anyhow, as mentioned, all features I'd love to add to habitctl (though learning Rust is a bit daunting.).

Reading List

While I'd love to take credit for a lot of these things, most of what I'm saying here is synthesized (read: stolen) from a number of books I've read, much experimentation, and what has worked for me. YMMV. Still, I'd recommend reading the following if you're interested in getting a bit better on the systems and habits path, and looking at both some some science backing habit formation as well as some very practical advice on how to incorporate what science lets us know about these things. In the order it makes the most sense to read them:

Allen's is the classic that minted the idea of GTD. Adams is hilarious, but talks a lot about systems versus goals and definitely started informing my thinking for this post (embarrassingly, two years ago). Duhigg's book teaches you about the neuroscience of habit formation, and making and breaking them, which is very helpful. However, for practical application, I was amazed at how useful Atomic Habits was. Clear, pragmatic, useful things you can do right away to start helping yourself out. It's almost the practical handbook that extends the theoretical underpinnings you see in Duhigg's book.

Would love to hear back from people on the post and if they have any other improvements or hacks or suggestions that have worked for them in a practical way. Feel free tp ping me @awws or via the email links.