I think of myself as not very conscientious. At school, I struggled with completing homework, sometimes not even turning in assigned essays. I forgot about deadlines and accidentally left my stuff behind. I did well on standardized tests because I could read quickly and eliminate probably incorrect answers, but other types of tests were a drag. There were some subjects I liked enough to do well in (well, mostly teachers I found engaging). For the most part, though, I didn't particularly care about grades. Even as an adult, I occasionally forget to finish something I'm working on, I lose things and time due to disorganization and attentional hiccups, and I've used my "Oops" fund a number of times. (W+ is more conscientious than I am, and occasionally patiently reminds me to take care of stuff.) I tend to follow the butterflies of my interest.

Fortunately, I've figured out some things that work well for me. Coding is great because even though it needs me to be pretty exact, I can work in small chunks, write tests to help me double-check, and automate repetitive tasks that my brain tends to hiccup on. When I worked at IBM, I had a lot of fun working on projects I cared about, like building systems to help professionals transition into teaching or helping food banks distribute food. I also did well skimming pages and pages of internal discussions so that I could summarize key themes for workshops. For my consulting clients, I tend to focus on prototyping their crazy ideas. If the idea proves worthwhile, we can then turn it over to other people to get it ready for production. Org Mode helps me keep track of what I want to do and when. In the Emacs community, I tend to focus on breadth rather than depth: Emacs News instead of package maintenance or core Emacs development. (And besides, it's volunteering anyhow, so when people bump into bugs in my code, it's either an opportunity for them to help out or something they might just put up with or work around.) I like experimenting, and I don't feel stuck; I can move on from an experiment when I've gotten enough data or when things change. I've shifted my life so that most of the tasks on my to-do list are things that I want to do that aren't time-sensitive, so I can do them when I want.

I recognize myself in other descriptions of conscientiousness. I like to plan and I like to take notes. I get somewhat stressed by the idea of being late, although I've learned to chill out a little about that because kids mean being flexible about time. I like considering decisions carefully and doing little experiments. I find risky behaviour stressful rather than fun. Still, I tend to think of myself as someone who doesn't do the extra work, who often doesn't pay attention to the fiddly details. A few counter-examples might help me figure out more about when my brain likes to spend the extra time on things:

• In a cryptography course that I took in university, we had an assignment to break a simple monalphabetic cipher. Each student was assigned one line. I had fun crunching through all of them (puzzles! piece of cake) and I distinctly remember relishing the teachers' surprise the next day.
• I signed up for more school, getting a master's degree in Mechanical and Industrial Engineering at the University of Toronto. I got interested in it for two reasons:
  • I enjoyed teaching computer science at my alma mater. Getting an advanced degree was strongly recommended. I experimented with a masters in education but I wasn't that interested in it.
  • I was also interested in personal information management thanks to Emacs and Planner Mode, so I was curious about exploring the usage patterns of people who had highly customized their PIM tool. Several papers in that area had been written by a researcher at the University of Toronto, so I applied there for a master's. That researcher left shortly after I arrived, so we looked around for another topic. Eventually we settled on social networking platforms in organizations, which was also interesting for me because it was about how people use technology to organize collective knowledge.
• I also signed up for parenting knowing that it's a ton of extra work including stress-testing my abilities, being responsible for helping an entirely separate little being figure out things I'm still figuring out myself, and handling endless problem-solving and adaptation in the face of uncertainty.
• I notice that I'm getting a little better at slowing down and practising piano, singing, and drawing. I've tried all these things before, but now I can approach it differently because I'm going into it with more life experience.
  • For piano, I can treat it like a moving meditation on the quirks of my monkey mind, and be amused at how my brain learns. I enjoy feeling the motions become more automatic. I also like the thoughts and memories that the pieces evoke. (As part of this beginner course I'm doing, I just practised a very simple version of "Thus Spake Zarathustra", which makes everything feel more epic.) Eventually I think it would be nice to be able to play the music that A+ and I might want to sing to. It seems to be my current hyperfocus. I enjoy spending the time practising, knowing that there's no way to skip that part (and perhaps this is even supposed to be the fun part).
  • For singing, I can be mystified by all the weird movements that I have to figure out in my larynx and my diaphragm and other parts I haven't even figured out how to name yet, much less activate. It gives me some empathy for how kids are learning about things we can't easily teach them.
  • For drawing, I can be amused by the gap between how things really are and how I imagine them to be, and the gap between what I imagine and what I can draw. The video tutorial assures me that taking the time to slow down and shade or add texture is worthwhile, and is even the fun part of drawing. I still get impatient occasionally (do I really want to spend all this time on one sketch?), but it's an interesting perspective. I think it might be nice to develop art into a relaxing activity. If I go through the steps, I'll probably get there. Also, I like doodling to break up the wall of text in a blog post like this one, so that's another fun way to practice.

So maybe I can be a bit more conscientious when it's something I'm curious about or care about.

For the tasks that I need to be conscientious about, there are other things that help:

• I'm getting better at accepting my limits. For example, when I had a pie in the oven last night, I told A+ that I couldn't go off to play Minecraft with her because I might forget about the pie and accidentally undercook or overcook it.
• Writing notes helps me keep track of where I am, what I wanted to do next, what I'm figuring out along the way, and so on. The possibility of sharing those notes (and thus having more opportunities to learn from my past self or from other people) also encourages me to get to a point where those notes can be shared. Here I really appreciate how Org Mode helps me capture, manage, and post my tasks and notes, thanks to literate programming. People occasionally tell me that they think I'm very organized, but that's probably just because I write about stuff so that when I forget, I can look them up again.
• Checklists are also handy. Most of the time, I just make a checklist on my phone using Orgzly Revived, but maybe I can make these more visual. I notice that I'm not particularly influenced by the gamification strategy of a streak count and mildly influenced by XP bars.
• Journal entries and blog posts also give me a record of what I've worked on, and even little bits of progress accumulate.
• I'm also learning to to distract the fidgety part of my brain with music or movement, and to manage it with timers. Timers are great. Timers to get started, timers to check in with myself, timers to come back…
• Automation is wonderful. Getting a computer to do the work is often more fun and less error-prone than my doing it myself. Even semi-automation is helpful.

Despite not thinking of myself as particularly conscientious, I'm pretty happy with what I've been figuring out about my life and the world. I can think of how I work as building on my strengths instead of just working around my weaknesses. I enjoy learning about and dabbling in lots of different interests, and the combination of ideas can be very useful (like dancer curiosity). Framing many decisions as experiments helps me get to 80%-fine quickly, and I don't spend a lot of time chasing down that last 20% that takes most of the effort. I don't fit the hustle culture of many self-help books, blogs, and videos, and that's okay.

I think my dad was not particulary conscientious either, at least not in terms of planning ahead, paying attention to details, following conventions. He was always in motion, happiest whenever he had a crazy project. Fortunately, he was really good at inspiring other people to handle the logistics. He came up with the ideas ("I want to fly across the Philippines in an ultralight") and people like my mom figured out how (fuel, landing spots, etc.). His spontaneous road trips drove me a little batty when I was a kid. But also, when it came to the things he cared about, he could spend hours, days, weeks on getting it right. I remember how he'd stay up late to figure something out, whether it was digital photography or Microsoft 3D Pinball. I've written about how he repeatedly drew variations on the same sketch in order to figure out what he wanted. He did okay. He found his way, even though it looked nothing at all like the standard paths. I'm probably doing all right, too.

My mom was more conscientious and deliberate than my dad was. She handled the business while my dad got to focus on his passions. From her, I picked up the habits of reading and writing. I think I'd like to be more of a mix between their styles rather than one or the other.

Apparently, conscientiousness tends to increase with age, so that's interesting. I feel slower when it comes to some things (probably because of adapting to all those distractions and periods of sleep deprivation, or maybe age, or simply a more realistic evaluation of my abilities), so it's easier to give myself time to do things that are slow. Maybe I'll get better at enjoying the act of practising and paying attention to the details. I'll probably benefit from more orderliness, too. I wonder how I can get my brain to enjoy decluttering and figuring out the right homes for objects. It's a little like preparing the space so that I can see what I like and it's easy to work on what I enjoy. (Marie Kondo's The Life-Changing Magic of Tidying Up might be relevant here, although even she has found keeping a tidy house with kids to be a challenge…)

I've been trying to think of a neutral or positively-coded word for the opposite of the conscientiousness personality trait. I asked Claude AI to generate a bunch of antonyms. I don't quite identify with "free-spirited" or "spontaneous", but I like "adaptable" and "improvisational," and "interest-driven" is an accurate description of the way we spend our energy. Those words don't quite cover the same cluster of meanings that "conscientious" does, but they give me other ways to think about the personality trait as something more positive.

I'm always curious about how I can work with what I've got. New challenges, new experiences, new capabilities… I get to learn even more about how my brain works and what I can do, especially as I build systems and processes to support myself.

Figuring out more about building on my strengths will also help me parent A+, so this work is extra worth it. I can even learn from the worries that sometimes flutter up when I see her also wandering far from what the school system would probably prefer that she focus on.

Thinking about processes and tools and self-acceptance also makes me think a little about Andy's recent blog post My 10 Years with Emacs, in which (among other thoughts about what he's learned about using Emacs and other people he wants to thank for helping) he mentions thinking of me as kind of the community mom. I was 18 when I started using Emacs, I've grown up in this community, and I've got blog posts and videos that help me catch glimpses of myself throughout the years. It does feel interesting to notice the shifts in my brain, from kind of an enthusiastic puppy bursting with energy to something more about experimentation, reflection, and connection. If I can get better at understanding myself and the tools I can build to support who I am and what I want to do, I wonder if that'll help other people too. I'm looking forward to being able to someday bring grandparent energy to this. What could that be like? There are people even older than I am in this community, which is wonderful. I'm looking forward to seeing how we all figure out how to work with what we've got.

I like looking for ways to reduce manual work or looking-up. I tend to have a hard time with tedious, repetitive tasks. I also keep an eye out for things I've been meaning to learn.

Small steps make it easy to squeeze in things here and there. I know my brain's going to suggest half a dozen things along the way, so it helps to start as small as possible and capture most of the other things in my inbox for later. That way, I can get to experience the benefits right away without feeling lost.

Another advantage of picking really small tasks and using Org Mode to capture the rest of the ideas is that I can try to avoid the Ovsiankina effect.¹ I spend most of my day taking care of our 7-year-old, so I squeeze in my focused-time tasks early in the morning before she wakes up. Sometimes I have little opportunities to work on things throughout the day, like when she wants to read a book or watch a video. She might do that for 15-30 minutes before wanting to connect again. If I pick the wrong-sized task or I don't dump enough rough notes into my inbox so that I can get the open loops out of my head and trust that I can pick things up again, the unfinished part pulls on my brain and makes it harder to enjoy time with her. Then I get tempted to let her binge-watch Minecraft or Rubik's cube videos² so that I can finish a thought, which doesn't quite feel like good parenting.

Lastly, I don't usually understand enough about my needs to build something complex from the start. Trying things out helps me discover more about what's possible and what I want.

Thanks to Emacs's amazing community, there are usually relevant functions or packages that I can borrow code from. I mostly have a sense of things from the blog posts and forum threads that cross my radar because of Emacs News, and I should probably get used to skimming the descriptions in the "New packages" list because that can help me find even more things.

When coming up with possible approaches, I also sometimes think about other related ideas I've had before. Filing those ideas into the appropriate subtrees in my Org files sometimes helps me come across them again. If I can take a small step that also gets me closer to one of those ideas, that's handy.

I also like to think about next steps and possibilities. For example, even if I spend an hour or two learning more about data visualization with Org Mode and plotting, that's something I can use for other things someday. This works pretty well with keeping things small, too, since small parts can be combined in surprisingly interesting ways.

In the course of writing this blog post, I learned how to use URLs in Graphviz, learned how to include inline HTML for export with @@html:...@@, used position: sticky, figured out how to highlight the SVG using JS, used CSS to make a note that should only show up in RSS feeds, and submitted a pull request for meme.el that was merged. And now I want to figure out sidenotes or at least footnotes that don't assume they're the only footnotes on the page… This is just how my brain likes to do things. (Oooh, shiny!)

I might take years before revisiting the same topic, so good notes can pay off a lot. Also, when I share what I've been working on, sometimes people e-mail me or comment suggesting other things that are nearby, which is a lot of fun. The ideas I come up with are probably too weird to exactly line up with other people's interests, but who knows, maybe they're close enough to what other people work on that they can save people time or spark more ideas.

Inspired by Mats Lidell's EmacsConf 2023 talk on writing test cases, I've been working on writing occasional tests, too, especially when I'm writing a small, function to calculate or format something. That's a good way of sketching out how I want a function to behave so that I can see examples of it when I revisit the code. Tests also mean that if I change things, I don't have to worry too much about breaking important behaviours.

How can I get even better at this?

• Popping the stack (untangling interruptions and ideas): When I let myself get distracted by a cool sub-idea, I sometimes have a hard time backing up. I can get back into the habit of clocking time and practise using my org-capture template for interrupting task so that I can use C-u with C-c j (my binding for org-clock-goto) to jump to a recently-clocked task.
• Braindumps can help me use non-computer time to flesh out notes for things I'm working on or ideas for next steps.
• If I skim the descriptions of new packages in Emacs News (maybe even the READMEs instead of just the one-liners), I'll probably retain a brief sense of what's out there and what things are called.
• Vector search across package descriptions and function docstrings could be an even more powerful way to discover things that are close to something I want to do.
• Using elisp-demos to add more examples to functions can help me look up things I frequently use but don't remember.
• Figuring out more modern IDE features like refactoring support, on-the-fly error checking, and code navigation could help me code faster.

So that's how I tinker with Emacs for fun: start with something that mostly works, keep an eye out for opportunities to make things better, use tinkering as a way to make doing things more fun, look for things that are nearby, and