Learning more effectively by exploring various unknowns

I’ve been thinking about how to learn better. Questions are a big part of that, I think. I enjoy learning the most when I have a question to explore instead of just aimlessly wandering around. Questions give me a sense of progress. Even difficult questions tend to have within them the seeds of their answers. I’d like to get better at this. After all, better questions get you better answers.

Brief update: What have I learned since my 2013 post on getting better at asking questions? I’ve gotten better at using outlines to map out my questions. I actually managed to sit through a couple of Coursera courses instead of losing steam mid-way, although I ended up skimming lectures and focusing on the homework. I’m still really bad at asking questions, whether it’s in a community like StackOverflow or asking specific people directly. I still read a lot, but my podcast-listening has dropped off the map due to impatience and to swapping this for playing video games during the rare commute. I still have a hard time sitting still for videos, although maybe this will come in handy for learning Japanese (videos with exact Japanese subtitles, perhaps?). I’m getting pretty good at taking notes along the way, untangling and keeping track of the little questions that pop up while I’m figuring things out.

There’s still a lot more to learn about asking better questions, though. I want to get better at asking small, concrete questions that yield some handholds and help move me (and other people) a little bit forward. Sometimes I find myself getting intimidated by questions that are too large or vague. Sometimes I catch myself retreading the same ground with no new insights or questions. (I sometimes get the sneaky suspicion I’ve blogged about something recently, but my searches don’t turn things up.) I’m fine with exploring questions that might only be relevant to me, but it would be even better if I can ask the question or phrase my answer in a way that other people can apply those ideas to their lives as well.

So here’s what I’ve been thinking about getting better at asking questions so that you can learn more effectively. I listed a few approaches that I use or that I want to explore, and I organized them into four categories:

  • learning about things I know I don’t know
  • learning about things I don’t know I don’t know
  • learning about things I thought I knew, but didn’t
  • learning about things I didn’t know I knew


I even came up with analogies! =) (Analogies are great. You can stretch them and figure out even more.)

Things I know I don’t know

Getting better at this will help me gradually expand what I know. This is the easiest category to work with. It’s like seeing a mountain in the distance and saying, “I want to go there!” There might be forests in the middle and you might have to turn back a few times to try a different route, but you have an idea of where you want to go and how you might get there.

I learn a lot in the context of projects I’m working on or things I’m curious about. I can get even better at this by:

  • Choosing goals or projects so that they build on top of each other, and asking questions that are aligned with those goals or projects
  • Going on learning sprints that focus on one topic, so I can take advantage of momentum
  • Reviewing my lists of previous questions and ideas, so that old questions don’t fall through the cracks

Things I don’t know I don’t know

This covers all the stuff other people take for granted that I just haven’t come across yet, and it also includes all the new stuff that we haven’t gotten around to creating or discovering. It’s like wandering around in the woods, not knowing that there’s buried treasure a few steps over there (or, alternatively, a nicely-shaped tree just perfect for afternoon reading). I can spend the rest of my life focused on the things I know I don’t know and that will be enough, but I like being pleasantly surprised by the things I wouldn’t even think of looking for.

The best way I get this is by reading comments on my blog, since people know about all sorts of stuff I haven’t come across yet and they generously share these tips. (You wonderful people, you!) I also read blogs, communities, source code, books, and indices as a way of stumbling across things that might be handy someday.

I can also get better by:

  • spending more time reading question-and-answer sites like Quora and StackOverflow
  • finding more blogs that ask interesting questions
  • getting the hang of using other people’s maps (courses, books, tutoring, etc.)

Things I thought I knew, but didn’t

You know that feeling when you start explaining something to someone and then you stop halfway through to look up the details? It’s surprisingly fun. =) It’s a little like when you’re asked to draw a map of your neighbourhood, or perhaps like writing a guidebook section about a few square blocks.

I can get better at this by:

  • Answering questions (either ones directly asked of me or in support communities)
  • Explaining things to myself and other people, discovering the gaps along the way
  • Reviewing old posts (things I used to know)

Things I didn’t know I knew

This is another fun category: the stuff that makes you go, “Huh. I didn’t know other people would find that useful.” Just like other people take stuff for granted (things you didn’t know you didn’t know), you take stuff for granted too. It’s like when someone asks you to recommend a place, and then you start explaining why you like this particular cafe, and in the process of explaining your recommendations, you realize all sorts of things that you appreciate about it but that you’d never actually thought about before.

Getting better at learning from the things I didn’t know I knew will help me get more out of my experiences, and it’ll also help me learn more deeply. Plus I get to help other people, too.

I can get better at this by:

  • Noticing what I do differently and explore why
  • Describing what I do and answering people’s questions; also, answering people’s questions in communities
  • Sharing more stuff

There are even more kinds of unknowns out there, and you can use different strategies to explore them. Taxonomies of the unknown has a fascinating list. I figure these four might be a good place for me to start, and I can’t wait to try out even more!

Connecting to previous thoughts and covering more ground

Sometimes I think I go around in circles, trying to figure out a recurring topic. Like this! I’ve written about this before. I want to get better at writing my way towards understanding. It’s like when I write, I’m so focused on adding just one more square foot to what I know. But I might not be spending enough time zooming up to make sure I’m going in interesting directions and that I’m not backsliding.

Maybe I need to pick up that pattern from programming with user stories: “As a …, I want to …, so that ….” As a learner, I want to get better at expanding on previous thoughts so that I waste less time repeating myself.

What is it, really? Let me dig around a little.

  • Not enough context/review: Is it that I write something, and then I discover I wrote something like it recently? No, I tend to be pretty good at finding 1-3 past posts related to what I’m thinking about.
  • Background : new thoughts ratio: Is it that I work in too small steps? What’s a good ratio? Background : thoughts : resolution : connection with others? Hmm, this might be interesting to quantify. Let me sample a few posts:
    • Post 1: 1 paragraph background, 4 paragraphs thinking, 2 paragraphs resolution
    • Post 2: 1 paragraph background, 7 paragraphs process description, 2 paragraphs resolution, 1 paragraph translation
    • Post 3: 1 paragraph background, 4 paragraphs thinking, 1 paragraph resolution.

    Oh, okay, that’s not too bad, actually. I do tend to have a certain “shape” to my blog posts: I think about stuff, and then I decide to try one or two new things. Also, my word count is nowhere near as high as I thought it used to be, which is good. My blog posts have a median of 500 words or so. Sometimes, if I remember, I’ll add a paragraph or two to help people translate things to their own experiences.

  • Not enough follow-up: Is it that I decide on something, but it doesn’t stick? I’m generally good at identifying one or two actions to try, and actually doing them (even if just for a short while). I’m not as good at following up on, say, books not stocked by the Toronto Public Library, because I’m lazy and my free backlog is infinite. I can learn to change that.
  • Not enough updates: Is it that I do stuff, but I don’t reflect on the update and share more notes? Hmm, possibly this; I do end up writing about things again, but it can be quite a while afterwards. Maybe I can schedule TODO items to update, and get back to keeping track of active experiments in my learning.org? That was useful. Why did I stop that? Agenda clutter? Worth revisiting. Also, sometimes I lose the references to interesting comments/conversations that recommended something. I’m generally good at looking up blog posts where I decided to do something, but I don’t track conversations as much. I’ve been trying to keep track of who recommended a book so that I can get back to them when I finally read it, which could be weeks later.
  • Not enough focus or structure: Is it that my posts are too scattered and don’t build up? A little of this, yeah, but I think that might be just how I work for now. I still have a hard time staying motivated enough to work to a larger outline. I talk about making little pieces that I could collect into larger things, but that’s passing it off to some smarter, more organized future self since I currently don’t do that kind of harvesting. This is something I could experiment with.
  • Not enough focus on helping other people: Is it that I feel self-conscious about focusing on internal discussions? Yeah, but it feels a little weird to tell other people what to do with their lives. Internal discussions seem to be helpful, and working out loud does help me get things done. I can be more didactic when I’ve earned it with experience, when I have the knowledge and reputation to back it up.

Hmm. Maybe it would help to imagine what awesomeness would look like, and then look into the differences between that and where I am now. Would it involve writing longer blog posts with larger insights, maybe aha!s that require significant non-writing time, so that there are bigger pay-offs for the reader? It’s the difference between

  • three posts that go, “Hmm, I’ve been thinking about this, and I’ll try this;” “I’m trying this, and this is what I’m seeing;” “I tried it and this is what I learned.” and
  • one post that says, “So last year I did this long experiment and this is what I learned.”

Nah, I like showing the in-between steps. It helps me think more clearly, and people often have great suggestions.

So small steps are okay, as long as they stick. Sometimes I review year-old posts and go, “Oh, yeah, I meant to look into that!” Other times, I look at those posts and go, “Yep, I did that and that definitely worked out well. That gives me new ideas…” I think awesomeness is more of the latter.

How can I get better at covering ground?

Part of this is getting better at remembering previously-covered ground (and keeping it covered).

  • I’m pretty good at searching my blog for posts I remember writing about the same topic, although there have been a few occasions when people have reminded me of things that I’d completely forgotten writing about.
  • I could make better use of my blog index by reviewing the general topic as well, which is a good excuse to refine the categorization.
  • Then there’s integrating those links to previous posts into my writing outline, building up bigger chunks.
  • And there’s also the power of the old-fashioned chronological review – simply re-reading old posts, maybe based on time. For example, when I do my monthly review, it might be interesting to reread the posts for that month, the month before, and the month one year before (or more). I might even challenge myself to schedule some of those posts for processing/updates so that I get practise in organizing and polishing previous posts.

Part of this involves clearly phrasing the question so that I can see the new ground to be covered. I’m not just thinking about a topic. I want to figure out something I didn’t know before. Here, for example, the central question that emerged after lots of outlining was “How can I get better at covering ground?” I learned more about the question while contrasting what I do now with what I’d like to be able to do. Working with outlines rather than prose for as long as possible seems to help, since it’s easier to cut and move around points, and it’s easier to see the bones of the post that I’m writing.

So that gives me a couple of things to try.

I know a few people who’ve made blogging part of the way that they learn, so I can learn from their examples as well. And there are non-blogging approaches, like the way W- keeps a professional notebook. So much to learn, and so many ways to do that better! =)

Sketched Book: The Stoic Art of Living: Inner Resilience and Outer Results – Tom Morris

Tom Morris’ The Stoic Art of Living: Inner Resilience and Outer Results (2004) collects easy-to-read quotes from Seneca, Epictetus, and Marcus Aurelius. The author glues the quotes together with commentary, providing context and suggestions for interpretation.

2014-12-10 Book - The Stoic Art of Living - Inner Resilience and Outer Results - Tom Morris

I like the author’s quotes from ancient philosophers, as other translations can feel stuffy. It’s a decent overview of interesting thoughts, and you can follow the ideas to their sources. The book can feel a little light, though. There’s something about the succession of quotes and topics that makes me feel like I’m bobbing up and down on a surface.

For comparison, I feel that William Braxton Irvine’s A Guide to the Good Life (2009) goes into greater depth for fewer concepts. Ryan Holiday’s The Obstacle is the Way reads more like a modern self-help book inspired by Stoicism, without as many quotes as this book.

If you’ve read a lot about Stoicism (and especially from the three philosophers featured here), you probably won’t find a lot of new ideas here. However, you might pick up some good phrasings and ways to think about those ideas. As Pierre Hadot wrote in Philosophy as a Way of Life: “Ancient philosophy was designed to be memorized, so that it could be ‘at hand’ when we are confronted with tumultuous situations.” Maybe you’ll find the quotes in this book easy to hang on to. Enjoy!

If you want, you can check out the books on Amazon:

I get a small commission if you buy the books through those links, but getting them from the library is totally okay too. =) Have fun!

Weekly review: Week ending December 12, 2014

This was a good week for programming and packaging. On my consulting gig, I got back into the swing of making small prototypes on the social business platform we use. I’ve been practising writing short Javascript functions, and they make my brain much happier. I also coached the other developer on our team over lots of instant messages and a few WebExes, and she’s picking up things nicely. I made progress on an annoying bug that has been plaguing us for a few months, too.

I’ve been working on getting more stuff out the door, too. I packaged the Emacs Chat transcripts as an EPUB/MOBI and sorted out a good workflow for publishing them. (Come to think of it, I should consider making a PDF version too.) While sketching a book, I noticed that “sketched book” is a fun way to refer to those visual book notes; since the domain was available, I registered sketchedbooks.com and set it up.

I want to get the hang of publishing things in chunks that are larger than a blog post. Collections are easy to start with. The next step would be to work on things with outlines and chapters and flows.

My energy’s slowly starting to return, yay! Slept more than normal – average of 9.3 hours a day – but that was because I was in bed for about 17 hours (!) last Sunday. I should be back to my regular ~8.3 hours of sleep a night soon.

Blog posts


Link round-up

… good haul this week. =)

Focus areas and time review

  • Business (34.5h – 20%)
    • Earn (17.5h – 50% of Business)
      • Earn: E1: 1-2 days of consulting
      • Earn: E1: 1-2 days of consulting
    • Build (13.1h – 38% of Business)
      • Drawing (7.7h)
        • Sketch JFS book
        • Make cover image
      • Paperwork (0.3h)
        • Actually submit tax return
      • Packaging
        • Format Emacs Chat transcripts as EPUB and sort out Org to EPUB workflow
        • Set up mailing list for sketchedbooks.com
        • Set up sketchedbooks.com – temporary site for now
        • Set up proper redirection so that I can do clever things with the URLs
        • Figure out EPUB workflow for publishing Emacs Chat transcripts
        • Set up EPUB workflow for Read Lisp, Tweak Emacs
      • Set up Authenticator
      • Set up app password so I can read Gmail from Gnus again
      • Fix OAuth login for Google – Quantified Awesome
      • Add Javascript for locating a blog post in my outline
      • Clean up disk space
      • Re-enter comments into Disqus
    • Connect (3.9h – 11% of Business)
  • Relationships (7.3h – 4%)
    • Chat with Sahil Sinha
  • Discretionary – Productive (18.3h – 10%)
    • Emacs (4.4h – 2% of all)
      • Finish transcript for Emacs chat
      • Revise transcript for Iannis Zannos
      • Revise transcript for Emacs Chat: Karl Voit
      • Patch https://github.com/jwiegley/use-package to mention :ensure t
    • Writing (10.1h)
      • Write about skewed notes
  • Discretionary – Play (6.6h – 3%)
  • Personal routines (29.9h – 17%)
  • Unpaid work (6.5h – 3%)
  • Sleep (64.9h – 38% – average of 9.3 per day)

Sketched Book: Just F*cking Ship – Amy Hoy, Alex Hillman

Amy Hoy and Alex Hillman wrote, published, and launched Just Fucking Ship in 24 hours, using a Trello board and an outline to quickly whip up this short reminder to stop procrastinating and get something out the door. They’re halfway through editing it and will post updates through Gumroad, so if you buy the book, you can watch it evolve.

I’ve sketched the key points of the book below to make it easier to remember and share. Click on the image to view or download a high-resolution version that you can print or reuse.

2014-12-12 Sketched Book - Just Fucking Ship - Amy Hoy and Alex Hillman

The principle I’m focusing on is #7: Start with atoms. I’m comfortable with making small pieces now: an outline, a blog post, a sketch. I’m working on getting better at assembling those pieces into molecules, and eventually I’ll be able to turn those molecules into rocketships. Eventually. But in the meantime, I can push more things out there.

I’ve been sorting out my EPUB/MOBI workflow by putting stuff up on Gumroad, like the Emacs Chat transcript collection. (Incomplete, but that’s what updates are for.) This will help me Ship More Stuff.

Today I noticed an opportunity for wordplay. The domain was available, so I jumped on it. Shipped.

Ship. Get your stuff out there, incomplete and in progress, because you’ll learn more from the feedback than you will from stewing on it by yourself. And if it flops? Don’t worry. You’ll do another one, and another one, and another one, and you’ll learn.

Want the e-book? You can buy it at Just Fucking Ship (Amy Hoy, Alex Hillman; 2004). You’ll get a PDF and updates. (Amusingly, no physical shipping involved.)

Like this sketch? Check out sketchedbooks.com for more. For your convenience, this post can be found at sketchedbooks.com/jfs. Feel free to share – it’s under the Creative Commons Attribution License, like the rest of my blog.

(Incidentally, I’ve quoted Amy Hoy before – see my post on Learning slack for another reflection on writing, productivity, and motivation.)

Building a better time machine

I’ve written before about how a blog is like a time machine, reflecting on my growth as a speaker or looking back over the past decade. It’s wonderful having all these notes. I often find myself referring to things from years ago – many of the technical posts are still useful, surprisingly – and then I bump into other memories nearby.

What can I do now to build a better time machine for me to use in another ten years or more? How can I tweak what I’m sharing and how I’m sharing it so that I can make the most of it? Let me think about how this has worked in the past, so that I can build on what’s been working well.

People like the tech posts, the workflow posts, the reflection posts where they recognize something they’ve been thinking about themselves. So those are all good. I also like point-in-time descriptions to help me remember what it was like. Maybe I’ll take those process journal entries and copy them in periodically so that they’re available somewhere.

I wonder: what other people have learned about writing for their futures? Here’s a snippet from Louise DeSalvo’s The Art of Slow Writing (2014):

p98. In her essay “On Keeping a Notebook”, [Joan] Didion describes what her notebook isn’t. It isn’t “an accurate factual record” because our recollection of an event might be vastly different from someone else’.s It isn’t to “dutifully record a day’s events” because that task inevitably becomes boring, and such a record conveys little or no meaning. Nor should we necessarily expect that we might one day open our notebooks and find “a forgotten account” of an event we can pluck for our work.

Instead, Didion believes that the notebook’s value lies in its record of “How it felt to be me” at a particular time. This, she says, is the notebook’s truth. Although we might imagine using it to fix our impressions of others, instead, “Remember what it was to be me: that is always the point” of the notebook. Part of a writer’s education is “to keep on noding terms with the people we used to be, whether we find them attractive company or not.” Reading our notebooks helps us to keep in touch with those past selves, and a record of “How it felt to be me” can be extraordinarily useful in writing memoir, creating fictional characacters, or writing poetry.

p100. Didion remarks on the fact that we change over time but that we forget the people we were: “I have already lost touch with a couple of people I used to be,” she says. Without a notebook record, these selves are lost to us. For a writer, “keeping in touch” with our past selves is helpful. … As Didion reminds us, “We forget all too soon the things we thought we could never forget.”

So, maybe the occasional snapshot of “How it felt to be me,” a way to remember that there are selves to remember. Otherwise the time blurs.

From that essay of Joan Didion:

Keepers of private notebooks are a different breed altogether, lonely and resistant rearrangers of things, anxious malcontents, children afflicted apparently at birth with some presentiment of loss.

I think that might be part of it, a little bit of that worry (not a lot, but it’s there, lurking in the background) that I might forget (no, will!) large chunks of my life, because even last month is a little fuzzy without notes and last year gets condensed into a few highlights. But no, that isn’t quite it either, since I don’t really hang on to the memories tightly even with my notes and my archive; I don’t reread, I don’t memorize.

Ah. I think this is it: my blog lets my past selves connect with other people who are looking for this stuff here and now (or in the future, as the case may be). So even if I am a different self–focused on other projects, learning about other interests–those past selves are there to nod at other people and share a little of what we’ve learned along the way. Mostly I leave things as snippets and blog posts, but on occasion, I consolidate things into summaries and documents – a clearer guide, a past self updated with a little present knowledge.