Daring The Improbable

Designing a Self-Friendly New Years Resolution That Will Stick

New Years Resolutions are as ubiquitous as they are ineffective. This post, however, is not about how ineffective they might be. You see, I have this idea that maybe its not our fault that we often can’t follow through on what we resolve to do. Maybe it’s a matter of bad design. In this post I’ll reflect on my previous resolutions to try and understand the many design errors behind them. And maybe, just maybe, by the end of it I’ll have guidelines by which I can make a more self-friendly (user-friendly) resolution.

1.) Not Planning for Failure

I’ve written about this before on my now-abandoned blog on medium. Essentially, we see discipline as this moving target where we only have it as long as we don’t fail. I’ve experienced exactly this. A few years ago, I wanted to get more serious about my running (definitely still should to do that, but that’s a point for later). I bought shoes, new tee-shirts, and so on, but then I missed a day because it started raining. Then I missed the next day for a reason I’ll mention next. But by the time I missed this second day I felt like a failure and wanted to distance myself from this failure.

So instead, let’s design failure into our design. Apps and websites don’t get designed around only the optimal digital native user, so why should your resolution be designed only for this hyper-unrealistic version of a person. We can do this in two ways, planning for failure days, and redefining failure per project (or resolution).

Failure Days

For whatever resolution comes out of this project, I’m going to plan weekly failure days. I’m going to let myself “fail” a day or two a week. This means that I don’t have to be perfect anymore; I’ve got failure days.

Redefining Failure

I’ve found that I have a general definition of failure and that if I don’t consciously define what failure means for a specific project, then my definition automatically goes to the default. This would be fine if I had a more healthy subconscious definition of failure, but I don’t. If I redefine my failure for this future, and still unknown resolution, as, say giving up completely on it, rather than not doing it 100% of the days that I’m able, I’m already looking at this from a more realistic and healthy point of view.

2.) Straight-up Forgeting

I’m not sure how common this problem is, to be honest. My memory is not the best, unfortunately, and not only that, but I tend to get so focused on certain things that other aspects of life fall by the way side. This usually results in me forgetting things like resolving to run more.

There is a problem that runs tangent to this one that makes sense to address here: I also tend to ignore notifications to myself to do things. For things that I should do, like play music more, I try to set alarms for myself. This categorically does not work for me. With my tendency to hyper-focus, I can’t promise that I’ll be receptive at a predetermined time or that. And I also tend to ignore things that seem to laborious to do. Accounting for this will help me massively in the long run.

3.) Should vs. Want

Most of my previous resolution designing has been around things that I should do. I should start running more, I should want to eat healthier, I should want to sleep 8 hours a day. Ideally, my wants would be aligned with that. Sometimes they’re something I want but not a high priority. Health is important, I wont ever say otherwise, but I often have real wants and desires that simply take priority and don’t give me much time to work with. The consequence of that is that I often prioritize family, and creative pursuits over, say, running.

4.) No Modularity

I didn’t know exactly what to call this section, so hear me out. I’m a person with both a wide array of interests that I let myself explore, but also an inner fickleness about what to pursue. One month I might want to focus on making art, and the next I might want to focus on writing. (I don’t think the English has a word with a positive connotation for this sort of phenomena. Fickle is the unfortunate word I have to use). This means that during the month of January I might resolve to do something that’s directly related to whatever I’m into at that time. But, as my locus shifts to the next subject, the resolution will eventually fade away.

So, what if I could have a modular resolution, something that will fit in multiple contexts. For instance, if I wanted to write more, instead of focus on strictly fiction or articles, I could use it as a modular resolution to write about whatever I’m into at the time. That way, when I inevitably shift focus to a new interest, I can keep my resolution in tact.

Designing The Resolution

I think I have enough here to design a resolution that is at least more resilient than ones I’ve made in the past. The rest of this article will introduce my design for my resolution and how it addresses the design brief above.

Resolution: Visual Journaling

My New Years Resolution for this year (yes, I’m announcing it early) is to incorporate a practice of visual journaling. Essentially, I want to have a way of visually depicting thoughts, ideas, and feelings. Why? I’m not sure really why. I find it endlessly fascinating that I’ve spent my whole life communicating with words and written language, but only until recently did I consider that I could participate in visual communication, even if it’s just to myself.

I’ve had moderate success with creating a journaling habit before, in part because I was already comfortable with the fact that I don’t have to write in it everyday. In that same vein, I’m giving myself permission to not draw anything in this visual journal if I don’t feel like it or if something gets in the way.

I’ll save point two for last, as I have the most to say about that one. As for point three, unfortunately, this article won’t cover the alchemy of turning a should to a want, because I very much want to do this.

For point four, I can see this being a practice that plugs into whatever future things that I get into. And, in fact, it might be interesting to see the intersection of this practice and what future things I might get into, there’s no telling what might lie there.

I’ll admit this second point is one of the most difficult. How can I remind myself to visual journal in a way that I might actually listen to (while also not getting on my nerves)? My first thought was to use something like Habitica. Gamification has helped me start habits before. The problem is that gamification, for me, turns a want into a should, violating item 3 above (and doing the reverse alchemy that I’m seeking to do with turning a should to a want). Then I found a great resource at hackingyouradhd.com. The podcast transcription goes into much more detail than I needed because the first point was exactly what I needed. My reminders needed to be immediately actionable. For instance, instead of a reminder that says “draw something in your visual journal”, it could say “put your journal on your desk” (and since it’s there, I might as well do some visual journaling, right?) My hope since its’ immediately actionable because I keep my journal next to my desk, the place where I’m most likely to be hyper-focused, that I can develop a regular practice.

This reminder problem isn’t done, though. I also need to set up some context, for the reminder. I’m not always by my desk at 8PM, for instance. One solution would be to carry my journal with me no matter where I go, but that would be tedious and I would grow to hate it. Would it be possible, instead, to set up a reminder for whenever I open up my browser of choice? Turns out, that’s not a functionality that people want or maybe its an untapped market, because I couldn’t find anything like that in my cursory searching. So what I did, is a wrote a barebones .html file and made it the homepage in my default browser. That way whenever I open it fresh (I do this once for work and then once in the evening when I sit down to do all my other hobbies), I get a very crude page telling me to put my notebook on my desk. How crude am I talking? This crude:

<p> Visual Journal </p>

But it works for me. I closed and reopened my browser after setting it up, saw the reminder and put my journal on my desk. It’s here next to me now.


Ultimately this journey is more about you, the reader, than it is about me. These four points above might not be the reasons that your resolutions and planned habits fall through, but if you can examine yourself, do research on yourself, you may start to see patterns that you can design around. This isn’t the final iteration of this design either. Likely as I’m going about my life I’ll experience something that I forgot to account for (one such thing that isn’t accounted for is travelling, for when that eventually becomes a thing again). As such there will definitely need to be something in place to deal with that scenario.

Designing for yourself is as fulfilling as it can be illuminating and I hope you have gotten even a little bit out of this journey along the way.


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