Category Archives: writing

Breaking down the skill of outlining

What do I mean when I say that I want to get better at outlining? What can outlining help me with, anyway?

Outlines are good for:

  • Capturing thoughts quickly: You don’t have to write full sentences. You can add keywords or phrases in any order, and you can flesh them out later.
  • Writing non-linearly: You don’t have to write one paragraph after another. You can jot down your key point, come up with a few supporting points, and then think about your introduction or conclusion.
  • Organizing your thoughts: You don’t need to always go from topic to detail. You can capture random thoughts and then group them afterwards.
  • Deciding on depth and coverage: How much detail should you include? What subtopics do you want to cover, and what will you save for another post? What can you cut, and what’s missing? An outline can help you discover these things before you spend a lot of time writing.
  • Rearranging topics for a more logical flow: Does it make sense to discuss one idea before the other? Fixing the flow in your outline saves you from rewriting all the transitions.
  • Writing quickly: If you’ve mapped out what you want to talk about, you don’t have to worry as much about writer’s block – all you have to do is follow the trail.
  • Picking things up where you left off: If you’re writing something that you can’t finish in one sitting (or if you want to be able to revise it easily even after some time), an outline helps you remember what you want to say and see what you need to do next.

Let me break outlining into sub-skills and think about different ways I can practise each of them.

  1. Outlining a single blog post
  2. Reverse outlining
  3. Outlining link-heavy posts or summary posts
  4. Outlining larger resources and books
  5. Outlining lifelong learning

1. Outlining a single blog post

I tend to write short blog posts focusing on a single question I want to explore or a point I want to make. This results in posts that are usually somewhere between 400 and 2,000 words. Although I’m comfortable with this way of working, I think outlining can help me organize my posts more effectively. Writing in paragraphs sometimes gets in the way of seeing the post as a whole or tweaking its flow easily. If I make an outline and then transform it into text, I find it easier to keep the whole post in mind as I write.

Because I use Org Mode for Emacs to write, it’s easy for me to work with outlines. I can hide and show parts of my outline using keyboard shortcuts. I can also keep a copy of the outline in one part of my window while I rewrite another copy of the outline into the actual text.

In addition to practising by outlining posts like this one, I can double-check the flow of a post while it’s in outline form, and I can also try different permutations of the order.

2. Reverse outlining

To create a reverse outline, start with an existing text. Identify the key points of each paragraph, and create an outline based on that. Organize those points into a more complex structure as needed.

I sometimes use reverse outlines with my own posts or drafts if I get the sense that things are a little out of order, but I can’t pin down why. With Org Mode, I can add list items before each paragraph, summarizing their key points. Then I can manipulate those list items with keyboard shortcuts, hiding the paragraphs or moving them around. When I’m happy, I can remove the outline structure and go back to working with paragraphs.

Reverse outlines are also useful when studying other people’s writing for content or for structure. They help you see the text as a whole instead of getting lost in paragraphs. I don’t do as much of this as I could. If I spent more time reverse-outlining posts that appealed to me, I could probably learn more about techniques for writing.

In addition to practising by creating reverse outlines for my posts and other people’s writing, I might find it useful to tweak Emacs for reverse outlining. I could write a function that automatically structures paragraphs into list items, and another function that extracts the paragraphs from the outline. Hmm…

3. Outlining link-heavy posts or summary posts

This is one step up from posts that deal with a single thought.

It can be challenging to write a blog post that links to lots of other blog posts. I find myself wondering where I want to go into more detail, how to avoid restating so much, how to bridge the different topics, and how to reconcile various types of writing.

I find outlines helpful for thinking about the structure of the post.

  • Should I bring in background information and then focus on a single question, exploring that in the body of the post?
  • Are the links tangential to the post, pointers for further exploration?
  • Am I trying to explain something to someone, and can I use links to let them dive down to the level of detail they want?

Outlines help me keep track of possible ideas to add and how to connect the different topics.

I write many posts that use links for background information or tangents, and the process for these is similar to the one for outlining a single blog post.

I don’t write many summary posts, though, and that’s something that I could practice. To do this well, I could pick more things that people want to learn (such as Emacs and Org) and write high-level overviews that link to more details.

One of the things getting in my way when it comes to working on summary posts, I think, is that it’s easy to pick the immediate benefit of moving myself forward a little, over the long-term benefit of teaching others (whom I could eventually learn from too). I can remind myself that I have plenty of time to write those exploratory posts, and that writing summary posts helps me consolidate, test, and share what I know.

4. Outlining larger resources and books

This is quite a few steps up from writing summary posts. I am not at all good at this yet, and will probably take a few years (at least!) to get the hang of it.

I practised a little this year by:

I tend to focus on writing the parts that are most interesting for me, so outlines sometimes make me feel guilty about the gaps. It turns out that working with existing material or committing to small chunks helps me get around challenges with motivation. I also do much better developing things in the open, getting feedback from people and revising things on the fly.

I’m looking forward to practising with 12-week courses, which make sense as the next small step to take.

5. Outlines for lifelong learning

Outlines can help with more than books and blog posts. I think they can help me learn overall, too. I think they might give me a way to place what I’m learning in context, connect things with other things I’ve learned or that I’m working on learning, capture threads that I’m not planning to investigate at the moment, and let me follow up with those threads when I want to revisit them.

I periodically update my learning plans, but I could give this more attention. Most of my learning notes are in my other Org files: rough notes by date in my journal, blog posts by topic in my index, outlines for things to write about in my sharing outline, and a high-level overview of evil plans.

There’s probably a better way to do this – perhaps incorporating my learning outline into my weekly and monthly review? I haven’t quite figured out how to combine past, present, and future in outlines in a way that makes sense to me while still making it useful to other people, like the way my blog index is useful because it’s not cluttered with other irrelevant points. Hmm.

Next steps

I hadn’t realized it before writing this post, but writing summaries and tiny guides (post-length, not book-length) would be a good in-between step for learning more about outlining before trying to tackle larger projects like books. A 12-week course of short tips might be interesting to do, too.

If you’re curious, you can find the outline for this post at . =)

How about you? What are the specific sub-skills you’re working on, and how?

Drawing thoughts on index cards

I’ve got quite a backlog of posts I want to publish, but I’ll squeeze this one in first. I want to think about how I can make the most of this new old (2011!) index card habit, and whether I should reconsider that voluntary bottleneck of publishing one post a day.

For the past two weeks, I’ve drawn at least five index cards each day. (You can find them on Flickr.) Each card explores a single thought. I like the way this lets me briefly capture what I’m curious about. I’ve included many of them in blog posts, grouping several thoughts into a larger chunk that’s easier to link to.

Still, at the present rate, my monthly review for January will link to well over 150 sketches. Perhaps I’ll change the monthly review section to list only the sketches that haven’t made it into blog posts yet. I’ve been keeping a digital equivalent of the roughly-sorted piles of index cards on my desk. It helps me see growing clusters of ideas and choose ones I want to develop with additional sketches or summarize into blog posts.

2015-01-14 Projecting my writing trajectory -- index card #writing

2015-01-14 Projecting my writing trajectory – index card #writing

Also, at the present rate of writing 1-3 blog posts a day (except for Thursdays, when I focus on consulting, and the weekends, when I focus on household life), I will keep accumulating scheduled posts. At some point, this will become unwieldy. It doesn’t make sense to schedule posts a year in advance. Even a backlog of three months seems too disconnected.

I can spend less time writing, but I’ve firmly wired it into the way I learn, so that’s hard. Alternatively, I could spend more time writing, developing thoughts over more time and packing denser experiences into a post. This approach might work.

2015-01-14 Projecting my trajectory -- index card #writing #sharing #pipeline

2015-01-14 Projecting my trajectory – index card #writing #sharing #pipeline

I can also get ideas out in other ways. My blog is the main archive I trust, but I can give myself permission to share one-off sketches on Twitter. For example, this sketch about keeping your drink safe from cats: it’s not quite a blog post and I don’t think I’ll develop the thought further, but it might be okay to share it on its own.

So, if I write blog posts for the thoughts that are already developed and tweets for the one-offs that won’t be developed further, that leaves the ideas that are waiting to be developed. They wait because I’m still figuring things out, or because they aren’t quite connected to other thoughts, or because my attention has moved on to other things. In Toyota Production System terms, they are muda – waste because of waiting or possible over-production.

I want to do better. What are some ways I can improve at this?

2015-01-16 Reflecting on reflecting with index cards -- index card #thinking #drawing

2015-01-16 Reflecting on reflecting with index cards – index card #thinking #drawing


2015-01-13 How can I do morning index cards more effectively -- index card #drawing

2015.01.13 How can I do morning index cards more effectively – index card #drawing

One way to reduce waste is to reduce quantity. Is five a good number for index cards, or should I reduce it to three? I think five works well for me. It forces me to dig deeper into a topic or to capture some of the other thoughts I have floating around.

Another way to reduce the waste in this process is to be more focused. If I think about and articulating 2-3 key questions for the week, that might guide most of my index cards. But then interesting ideas come up during the week, and I draw lots of cards for those as well. I turn many of my index cards into blog posts on the same day, so within each day, there’s focus. If I try to use any “extra” index cards to build on a previously-drawn thought, that helps me connect.

A third way is to reduce my attachment and let things go. Perhaps I might decide that after I make a monthly index of unblogged cards, I’ll clear that index and archive the physical cards. That way, each month starts fresh, but I still have the ability to go back and look for those roughly-categorized cards in case I have an idea that’s strongly connected to that. I don’t have to worry about visualizing this archive, tracking my statistics, using all the dangling threads, or getting to 100% use.

So that can help me deal with index cards, but what about blog posts? The benefits of limiting my blog to one post a day are:

  • I occasionally add to or revise a scheduled post, especially with feedback from sharing drafts
  • I can schedule different kinds of posts for a week, turning my sprint-type learning into a variety that helps readers
  • People don’t get as overwhelmed (although daily posts are already more frequent than most other blogs do, and I’m pleasantly boggled that this is the most frequent option chosen by people subscribing to the mailing list)

The downsides are:

  • If I write something useful, whoever searches for it while it’s in hidden draft mode won’t come across it, but I guess that’s almost the same as if I hadn’t written it at all
  • It delays the feedback cycle
  • Sometimes posts get out of date

One option is to go back to publishing two posts during the weekend: a weekly review, and maybe another thinking-out-loud/reflection post, since that’s the one that has the most surplus.

Another option is to post two times a day. I’m a little less keen on that, although it might be doable if I can keep my main archive but split off specific, lower-traffic, topic-focused views that people can subscribe to.

A third option is to write longer posts. I find my constraints on chunk size to be helpful, so maybe not.

Hmm. Maybe I’ll publish two posts during weekends, and then revisit this when I find myself scheduling three months out… =) Suggestions?

Think more effectively by typing to yourself

Whenever I need to think, I often switch to my text editor and start typing. Whether I’m coding, debugging, making decisions, or simply figuring things out, I find that typing helps a lot.

Typing keeps a record of your thoughts, which is invaluable when it comes to untangling complexities or picking up where you left off after interruptions. Typing feels more socially acceptable than talking to yourself out loud. You don’t interrupt other people’s thoughts. You might even look like you’re doing serious work – which thinking is, but it’s sometimes less obvious when you’re just staring into the distance. You feel a sense of progress, and you can stop yourself from endlessly retreading the same topics.

I sketch my thoughts on paper if I want to play around with visuals or if I want the big picture, but typing feels more useful for having internal conversation, including links and references, and covering lots of ground.

I type at ~120 words per minute, which lets me keep up with my thoughts. I think faster than this, or at least I think I do. But when I think without typing, I often feel my mind jitter between topics like a squirrel on a sugar rush. Handwriting is too slow, talking out loud too ephemeral. Typing is just right. It slows me down just enough to keep my thoughts coherent.

(And really, when I measured how fast I type when I’m copying something and how fast I type when I’m coming up with something from scratch, the result was clear: thinking is the slow part of this process, not typing.)

I often use typing as a way of talking to myself, much like you would talk to someone over social media or instant messaging. I ask myself questions. I explore my uncertainties. I tell myself things that I know or that I want to find out. I put on different hats, adopt different perspectives. I make progress, and I can see that progress. Sometimes it almost feels like I’m simply transcribing a conversation that I’m observing. I can focus on typing and let my thoughts go where they want.

Typing lets me write and think non-linearly. I jump around, fleshing out points, following up on thoughts. Sometimes I organize my thoughts into outlines or link between ideas. As I type, I notice interesting questions or ideas and mark them as TODOs. I can flag them without losing my train of thought or worrying that I’ll forget about them.

At the end, when I’ve written my way towards understanding or resolution, I can step back to get a better look at the choices I’ve considered and my reasons for choosing. I’ve got something that I can extract TODOs from or even neaten up into a blog post. I keep the rough notes in my journal, which is part structured review and part brain-dump of whatever I’m thinking about. That way, I can review these notes, months later, to improve my understanding, see if I made the right decision, and think about what else I would like to learn or do next.

Here’s an excerpt from one of my journal entries:

What’s good to do now, after the sketchnote?

I should focus on other things, I think – limiting flow to encourage balance and planning ahead instead. Besides, I already have three sketchnotes queued. I don’t need to draw my way into February, and I can learn from people’s feedback in order to improve the next sketch. So it’s okay to spread it out to one sketch every other day or so. I’ll try a two-week publishing frequency first, and then I’ll up it to weekly if I manage to queue enough. (Editorial Calendar is handy!)

I think it would be interesting to tweak Emacs to make this sketchnoting workflow even more effective.

How would I do that?

Well, for starters, I can write some Emacs Lisp that copies my basic template, renames it appropriately, adds the date, adds the property, and links to the file. Wouldn’t that be cool?

I wonder if i can drive the redirection from Emacs Lisp as well. I don’t have to do it in WordPress, after all. I can get a snippet that I can copy and paste into the Nginx site configuration for sketchedbooks. Mwahahaha.

Typing to yourself is even more effective when you’re trying to write or debug code. I use Org Mode for Emacs, so it’s easy for me to include links to StackOverflow answers that I’m trying to apply, source blocks with code I’m experimenting with, descriptions of approaches I want to try… If the comic “This is why you shouldn’t interrupt a programmer” resonates with you, then you know how useful it is to have notes on what you’re trying to figure out.

If you’re frustrated when you can’t pin down your thoughts, if you find yourself circling topics but not making much progress, consider typing to yourself. If you don’t type fast enough and you find yourself getting annoyed, invest the time in learning how to type faster so that you can reduce the friction. If you type fast enough to keep up with your thoughs, try using a conversational approach, talking to yourself with different perspectives. Might be a handy way to think more effectively. Good luck, and tell me how that works out for you!


Deliberately making sense

When it comes to connecting the dots between ideas, would you rather be methodical or inspired?

We prize the flashes of genius, the intuitive spark. We idolize inventors who bring together ideas from different fields in a brilliant moment. The tortoise wins in children’s books, but history belongs to hares.

I would rather be methodical, I think. I’d rather get better at taking lots of small steps instead of counting on big leaps. I plan assuming mediocrity, not talent, and then I try to build towards excellence.

Just relax and the ideas will come to you, people sometimes say. Yes, I do some of that, but I’m more interested in conscious, deliberate action. The sparks will come when they want, but in the meantime, why not get better at preparing the groundwork or making progress? I think you can get better at making sense of things, coming up with ideas, seeing gaps. This is a skill you can develop. You’re not limited to waiting for a fickle muse or wishing you’d been born a hare.

The aha! moments of unconscious connection seem to come more readily when you keep more thoughts in your head, because you have more opportunities to connect the dots. I try to keep very little in my head, as I’m both forgetful and distractable. (I suppose this self-image is something I can change, but it has useful consequences, so I keep it.) I write down as much as I can, which frees me up to remember only hooks and summaries that let me look up more information as I need it.

In fact, I often choose slow exploration instead of a whirlwind of insight. I’d rather take notes as I think instead of jumping from one topic to the other, even if observation changes the nature of thoughts. After all, there are plenty of times when I can think but I can’t write, so I can let my mind meander then. When I’m near a computer or notepad, I may as well take advantage of those tools. If I can capture a thought, then I can remember it, and this helps me build up knowledge over time.

Instead of relying on my brain to trigger an aha! moment out of the blue, I usually reflect on a single topic and see what other associations it brings up. I might link to other blog posts or sketches, include book excerpts, or dig through my private notes for more thoughts. Most of these reflections take small steps forward. Others bring together two or more streams of thought.

I’m often limited by my forgetfulness. I may remember a few relevant references, and I search my blog and my notes for more. However, I don’t always cast a wide enough net. There’s a difference between knowing you’ve forgotten something, and not even thinking that you’ve forgotten something. The first is annoying, but the second is a bigger missed opportunity.

The best way around the associative limitations of my brain seems to be other people. I love it when people tell me how something I’ve written reminds them of a book or someone else’s blog post (sometimes one I’d read and forgotten, sometimes completely new to me), or even how it reminds them of another post of mine.

I can’t count on people to suggest the missing links for most things, though. Fortunately, computers are getting better at suggesting associations. Search engines help when you know what you’re looking for. When you don’t, other tools can analyze what you’re working on and suggest items that are similar in content. I often use Amazon’s book recommendations to find other books I should read. I’ve played around with Remembrance Agent before, and have often envied Devonthink’s ability to suggest related notes. Evernote just released a new Context feature that’s supposed to do something similar. I prefer Emacs for writing anyway, and I don’t have something quite like that set up yet.

The more manual approach of keeping a categorical index of my blog posts lets me get a quick overview. When a category grows too large, I usually break it down into smaller groups. I also take advantage of the juxtaposition of posts in my blog archive when I do my monthly and yearly reviews. Taking a step back helps me see the patterns in my thinking.

Other aspects of connecting the dots also lend themselves to deliberate practice, focusing on one sub-skill at a time. For example, when I read a book, I can practise taking a few moments to place it in the context of other books I’ve read about the topic. With which other books does it agree, and where does it diverge? Thinking about this process lets me isolate and get better at one specific aspect at a time, and that helps me improve as a whole.

Another benefit of using explicit processes to help me make sense of things is that other people can try what I’m learning. I care less about idiosyncratic leaps dependent on individual talent and more about improvements that other people can experiment with. For me, it makes less sense to tell someone, “Be more creative!” and more sense to say something like, “Forced associations are a way to enhance your creativity” and share examples. If I think about how I do things–how my processes are similar to others’, and where it diverges–I can describe them to other people, who can pick up ideas and give me feedback.

So that’s why I choose to be a slow thinker, making sense through process rather than intuition. But I’m getting faster at slow thinking, and that’s opening up more possibilities. I grew up speed-reading and touch-typing, which is a good pair of advantages. To that, I’ve added programming, automation, writing, and different types of note-taking. I’m working on getting the hang of outlining, indexing, reviewing, and synthesizing. There’s a lot to learn, but I’m confident that I can keep improving.

I love swapping notes with other people who’ve made similar choices–the slow thinkers, the methodical ones, the ones who have thought about how they do things and how they think about how they do things. I’m not looking for fast fixes or magic solutions, just ideas for little experiments to try.

Hares might make for better stories, but tortoises have more tricks to share.

Possibly related:

Kahneman’s Thinking, Fast and Slow feels a little related to this thought too, but it’s not quite the right fit.

Do you have any favourite tricks for slow thinking? Are there any tricks I use that you’d like to learn more about?

Predictable advice about productivity

Let me think out loud a bit about this, since there’s something here that I want to dig into.

Someone asked me if I’d consider answering the question “What’s your morning ritual/routine that helps you stay productive and organised throughout the day?” for inclusion in a blog round-up.

Ordinarily, I’m not too keen on answering surveys or filling out questionnaires from people. I know it’s a popular content-generation technique and that bloggers like doing it because it encourages people to link, but there’s something about the format that feels a little meh. I’m even less enthusiastic about blog roundups because the typical format–a list of names, links, and a quoted paragraph or two–doesn’t lend itself well to nuanced observation or discussion.

Still, I’d been thinking about reflecting on the topic for a while, so I bumped it up my list of things to write about and drafted this: Relaxed routines.

I sent a sneak peek of the draft to the person who asked me, and he responded:

The fact that you wrote “Sometimes I think of three things I would like to do that day, and I type a few notes and thoughts into Evernote” is very interesting because other experts also think of 3 things they want to do every morning and go after them.

And I thought, no, that’s not the point I want to make. Which made me think: What is the point I want to make? I said:

When you write, don’t look for the same, old, common, generic advice. Look for what’s unusual or unintuitive or idiosyncratic.

Come to think of it, I should probably expand on this thing about slowing down, taking notes, and sharing them, since a lot of people are worried about interrupting momentum or giving away their secrets. To me, that’s more interesting than picking a few priorities for the day, which (as you noted) many other people do.

So there’s an interesting thought there that I’m going to flesh out and add to the draft. Perhaps by the time you read this, I’ll have already added and posted it.

Anyway. This got me thinking about the predictability of most productivity advice. If I crack open a newly-published book on productivity or click on one of the countless blog posts that flow into my streams, I know that more likely than not, it will tell me to: Wake up early. Prioritize. Don’t start with e-mail. Take care of your health.

It’s about as surprising as reading a personal finance book that tells me to spend less than I earn. Granted, there are probably lots of people for whom the repetition of these concepts helps.

I wonder how to go beyond the same old advice. What kinds of information have been helpful for me when I want to change? What would be more helpful for other people? How can I go beyond writing generic thoughts myself? How can I notice and dig into the differences? How can I learn from more divergences?

Here’s what I’ve found helpful:

  • Collections of different approaches, so that I can experiment and find out what works for me. I don’t read books looking for the One True Way to manage your tasks. I look for the diversity of systems described by different people so that I can extract ideas that I can play around with. That also means that I don’t want trite advice that I already have previous samples of. I’m looking for new stuff, things to make me go “Hmm, let me try that.”
  • Pointers to interesting people, which is related to the first benefit. For example, when reading about how scholars managed information before computers (Too Much to Know: Managing Scholarly Information Before the Modern Age), I came across historical role models like Seneca and Pliny. That led me to learn more about their stories so that I could understand their techniques in context. It isn’t just about isolated pieces of advice, but people whose lives that advice came from and why they learned that. Plus points for people I can identify with or be inspired by: “Oh, she did that, so I can probably pull off something similar too!”
  • Behind-the-scenes thoughts: Reading people’s thoughts about their own systems is more interesting for me than reading people’s conjectures about other people’s secrets. I like reading blog posts from people who are thinking out loud, because that lets me peek into other people’s thought processes and watch how they learn. I like seeing the in-between stuff, not just the polished products.
  • Reflection questions, so that I can direct my awareness to things I might otherwise overlook, and so that I can evaluate things.
  • Research, particularly with non-intuitive results. For example, applied psychology tells us our brain is subject to all sorts of fallacies, and being aware of things like sunk cost fallacy helps me try to correct for them.

So with that in mind, how can I improve that reflection on routines so that I and other people can get more value from it?

Let me think about potential points of divergence from common wisdom, and why I’ve chosen those ways:

  • I sleep in instead of getting up early. For me, it’s important to mostly go to bed at the same time W- goes to bed (unless he’s staying up really late). Since that’s usually between 12 AM to 1 AM and I need a bit more than 8 hours to feel well-rested, this means I usually get up between 8:30 and 9:30. I organize the rest of my schedule around this, including avoiding all morning meetings.
  • I follow my energy instead of forcing myself to stick to a plan. I used to block off time to work on specific things, but I realized that I enjoy flexibility and I work better with an open schedule. More about this.
  • I don’t make specific, measurable, time-bound goals. I found that I’m not motivated by “urgent” deadlines that I set myself. Instead, I keep a large list of small tasks, and I use those to keep moving forward on different things.
  • I slow down to take notes. Many people tell me they don’t have the time to take notes. I make note-taking part of the way I do things, whether it’s thinking about a decision, learning about a new topic, or debugging a problem. It’s not really slowing down, actually. I suspect that I make slower progress when I don’t take notes, because my mind gets more jittery and has to cover the same ground repeatedly.
  • I share what I’m learning. People are often concerned about giving away their secrets, looking foolish, or letting go of competitive advantages. I find that blogging helps me learn more, connect with interesting people, and get more stuff done.
  • I don’t worry about being responsive. I’m very casual about responding to e-mail and blog comments. I can go a week or two (and sometimes more!) before replying, although I check more frequently than that. I treat them as long-term asynchronous conversations, not as firm commitments. This lets me see my e-mail mostly positively as a source of interesting questions and ideas, rather than as an obligation that gets in the way of Real Work.
  • It’s easy for me to choose slack over status or stuff. This is more of a personal finance thing, I think. I’m picky about the things I swap my life for, because I prefer space, freedom, and resisting hedonic adaptation. This is why it’s easy for me to ignore advertising.
  • I’ve shut up the “You’re not an artist!” internal self-censor so that I can use visual thinking to explore ideas. People often tell me that they wish they could draw sketchnotes too. Pointing out that I draw like a 5-year-old still doesn’t seem to be enough to help them get over that mental barrier. Someday I’ll probably figure out how to help people hack around that.

For each of these choices, there are probably thousands of other people (at least) who do the same thing. That’s okay. In fact, that’s terrific, because then we can swap notes. =) I don’t have to say totally unique things. I’m not sure I can. I just want to add more to the conversation than generic “advice.”

So how do those choices influence my everyday routines? Well, waking up when I feel like it is an obvious one. Writing, drawing, and publishing throughout the day is another. This 5-year experiment is another result of those choices.

The most useful change that people can experiment with, I think, is the one of writing stuff down, even if they don’t publish it. Not just plans and reviews (although those are good places to start), but the in-between stuff, the “I’m not entirely sure where I’m going with this” stuff. It could be a text file or a document or a paper notebook – just somewhere you can leave breadcrumbs for your brain so that you can come back to things after interruptions and so that you can go back in time.

But journaling is also part of the set of standard productivity advice, so what can I add here? The reassurance that no, it doesn’t make you go slower, it actually lets you cover more ground? A demonstration, so that people can see what that looks like (especially over years)? Workflow tweaks to better integrate it into the way you do things? Personal knowledge management ideas for organization? Surveys of other people’s systems so that we can pick up great ideas?

If I want some fraction of the people who read me to pick up this writing habit, what I can do to help them (you!) get over any barriers or excuses?

That’s what I should write. I’m not going to be able to trigger that epiphany in one excerpted paragraph in a list of twenty or fifty or people. But I can always explore the idea on this blog (with your help =) ), and other people can link to or summarize whatever they want, and who knows what conversations can grow.

Start your titles with a verb to make them stronger; or reflections on titles, filler phrases, and my life as a gerund

Instead of using a generic title (ex: Top 10 Ways to …), pick your strongest point and put that in the title as a clear recommendation.

Now that I’ve gotten that promised tip out of the way, here’s the reflection that prompted this post.

Many bloggers focus on improving their titles as a way to encourage people to click or share. Having repeatedly run into the limitations of my blog searches and index, I’ve been thinking about blog post titles as a way to make my blog posts more memorable – both in terms of retrieval (remembering what to look for) and recognition (recognizing it when I come across it).

That’s why many of the usual title-writing tips don’t appeal to me, even if they’re backed by A/B testing. List posts? A focus on new or exclusive information? Mysterious headlines? While writing a post called “10 New Emacs Productivity Tricks That Will Make Vim Users Hate You – #2 Will Save You Hours!” is tempting to consider as an April Fool’s Joke, that kind of title is useless for me when I’m trying to find things again. Any title generic enough to come out of a blog post title generator is too generic for me to remember.

Fortunately, there are plenty of role models on the Web when it comes to writing clear, specific blog post titles. Lifehacker somehow manages to do this well. Most of its posts start with a verb, even when linking to a post that doesn’t, and yet it doesn’t feel overbearing.

Here’s a sample of Lifehacker titles for posts that summarize and link to other posts (ignoring posts that were original guides, product links, or fully-reposted blog posts):

Lifehacker title Original post
Re-Read Old Books After a Few Years to Gain New Perspective How you know
Agree On a Special Signal So Your Colleagues Can Reach You On Vacation 11 Valuable Tips for Handling Emails While on Vacation
Find the Best Thrift Stores Near You Using Zillow and Google Maps How to Find the Best Thrift Stores in Your Area
Find a Hobby by Rekindling Your Childhood Passions 7 Strange Questions That Help You Find Your Life Purpose
Conduct a “Nighttime Audit” to Sleep Better How to Spend the Last 10 Minutes of Your Day
Get Your Ideas Out of Your Head to Start Improving Them 6 Lessons from Pixar that Will Set You Up for Success
Focus on Discipline More Than Motivation to Reach Financial Goals Forget Motivation, This is the Key to Achieving Your Goals This Year
Give Yourself a Creative Game Each Day to Boost Inspiration The Importance of Personal Projects
Fix Your Bluetooth Audio in Yosemite With This Terminal Command Commands to Make Yosemite Suck Less

Fascinating. Of the nine posts I looked at, all of them rewrote the titles from the original blog posts so that they started with a verb, making the titles more specific in the process. This makes sense in the context of it being a lifehack, of course. The concept has action at its core.

I like the new titles more. I can imagine that remembering and linking to the Lifehacker-style titles would be easier than linking to the original ones.

Most of my posts don’t quite feel like those, though. I noticed that most of my titles start with gerunds: thinking about, building, learning, exploring, experimenting. I think it’s because I write in the middle of things, while I’m figuring things out. I don’t feel comfortable telling people what they should do. I share my notes and let people come to their own conclusions. Starting a post with a verb seems to be too direct, as if I’m telling you to do something.

That said, filler phrases like “Thinking about…” aren’t particularly useful as part of a title, since the reflection is a given. But changing “Thinking about how to make better use of Yasnippet in my Emacs workflow” to “Save time with dynamic Yasnippets when typing frequently-used text in Emacs” doesn’t seem to accommodate the exploratory bits, although it could be a good follow-up post. Changing “Minimizing upward or downward skew in your sketchnotes” to “Minimize upward or downward skew in your sketchnotes” feels like I’m making a value judgment on skewed sketchnotes, when some people might like the fact that an upward skew tends to feel happy and optimistic.

So I use nouns or gerunds when reflecting (which is self-directed), and verbs when I’m trying to put together other-directed advice. This helps me differentiate the types of posts in my index and in my editorial calendar admin screen, and it also signals the difference to people as they browse. You might not be interested in my reflections and prefer to focus on tips, for example, or you might be tired of tips and want journal entries instead.

That works because those types of posts are generally quite separate. When I want to help someone learn a technique such as sketching quick ribbons, I don’t go on an extended tangent about how I learned how to do that or how I want to improve. When I’m thinking about how I can improve my delegation skills, I don’t expect someone to patiently go through all of that in search of three concrete tips to help them improve. I think that as I gain experience and become more opinionated (the latter probably being more related to this), I’ll write more advice/instruction posts, possibly linking to those personal-experience-and-reflection posts instead of going on internal tangents.

In this post, I’m experimenting with a verb title while doing extensive self-reflection. It feels a little odd, as if you started a conversation with someone and then proceeded to talk to yourself, idly musing out loud. You’ll have to tell me if I should never do that again, or if there’s a way to manage the balance. But it also feels odd to use my part of the conversation to tell you to do stuff, solely drawing on other people’s research or recommendations, without sharing my context so you can tell if something that makes sense for me might make sense for you. I figure there are plenty of other people out there who want to tell you what to do with your life, and I’m not completely fond of that approach anyway. And it also feels odd to natter away about my life like a self-absorbed ninny, making you do all the hard work of translating ideas into things that you can actually use. I still haven’t completely figured out how to make personal blogs more useful for other people.

Could I make an idea sandwich: summary and research at the top, personal reflection in the middle, call to action at the end? Maybe that could work.

Still, I want to do something with my titles so that I don’t end up with lots of “Thinking about …” and “Exploring …” and “Deciding between …” that blur in my memory. My ideal for these reflection posts, I think, would be a clear, concise summary of the key insight (perhaps saving it as an excerpt as well, if it doesn’t fit in the title). If I followed that up with an other-directed post with a crisp title that started with a verb, made the recommendation, brought in some research and observations, and linked to my reflection, that would give me a good, logical, memorable, useful chunk that I could share with other people.

Right. That makes sense to me. If I address you with a direct verb or “How to …”, I should deliver a post that requires minimal mental translation for you to get good tips out of it. If I clearly mark something as a reflection, you know what to expect. I tend to remember them as actions I decided to take (“The time I resolved to…”) or the particular new thing I came to understand. I can take a few minutes to update the titles and summaries accordingly, which could help me years later when I’m trying to make sense of things again.

In Buckminister’s somewhat strange book I Seem to Be a Verb (1970), he wrote:

I live on Earth at present, and I don’t know what I am. I know that I am not a category. I am not a thing—a noun. I seem to be a verb, an evolutionary process—an integral function of the universe.

A verb seems too definite for me. I’m a gerund in at least two senses, I think: reflexive, the way “I read” is an act but “reading” is a noun that lets us talk about itself; and in the process of doing, not done.

Do you write other-directed posts that offer advice or instruction? Consider lopping off “How to …” and “Top 10 ways to…”. Start with a verb and give one clear recommendation. Do you write self-directed reflections? See if you can harvest the ideas for other-directed posts, and perhaps invest a little time into making your posts easier for you to remember. Do you write a mix of both, and have you figured out a good flow? I’d love to hear what works for you.