“What tools should I buy?” “What platform do I start with?” “What's the best option out there?” Geeks have a special case of analysis paralysis at the beginning of things. We try to optimize that first step, and instead end up never getting started.

Here's what I'm learning: In the beginning, you're unlikely to be able to appreciate the sophisticated differences between tools. Don't bother spending hours or days or weeks picking the perfect tool for you. Sure, you can do a little bit of research, but then pick one and learn with that first. If you run into the limits, that's when you can think about upgrading.

Start with something simple and inexpensive (or even free). If you wear it out or if you run into things you just can't do with it and that are worth the additional expense, then decide if you want to get something better. I do this with:

• Food: We start with inexpensive ingredients and work our way up as necessary.
• Shoes: Upgraded from cheap to medium.
• Bicycles: Still on the first bicycle I bought in Canada, since it was enough for me.
• Ukeleles: Glad I just bought the basic one, since it turns out it's not quite my thing.
• Knives: Okay, we splurged on this one and started with good knives, since I piggybacked off W-‘s experience and recommendations.
• Drawing: I tried the Nintendo DS before upgrading to a tablet and then to a tablet PC. For paper, I tried ordinary sketchbooks that cost $4.99 on sale, and have been happy with them so far – although I might downgrade to just having a binder of loose sheets.

Don't worry about what the “best” is until you figure out what your actual needs are.

There are situations in which the cheapest or the simplest might not be the best place to start. You can easily get frustrated if something is not well-designed, and some inferior tools like dull kitchen knives are dangerous. That's a sign that you've run into your choice's limits and can therefore upgrade without worry. Yes, it might waste a little money and time, but you'll probably waste even more time if you procrastinate choosing (more research! more!) and waste more money if you always buy things that have more capacity than you ultimately need. You can tweak how you make that initial decision–maybe always consider the second-from-the-bottom or something like that–but the important part is getting out there and learning.

“You're pretty organized, right? Do you have a system for productivity that I could use?” someone said to me. She sounded frustrated by her lack of progress on some long-standing projects. I shrugged, unsure how to help.

I don't consider myself super-productive. I am, however, less stressed than many people seem to be. I've been learning to keep realistic expectations, get rid of less-important tasks, and work in quick, small, useful chunks.

Realistic expectations: We tend to overestimate how much we can do, particularly if we're looking a week or two ahead. Even if last week was derailed by interruptions, we hope next week will be a smooth ride. I'm guilty of this myself. I compensate by expecting little of myself – just one to three important tasks each day, moving forward a little bit at a time. If I find myself with spare time and motivation, I check my other tasks for something to work on. It's okay if I end up procrastinating something. That usually means I spent the time on something I valued more.

Ruthless elimination: “But how do I motivate myself?” This is another thing that people often struggle with. I use different strategies depending on what I need. For example, I'm currently working on a project with a high risk of failure and a fair bit of work. For me, it helps to amplify the perceived benefits, downplay the small pieces of work that I need to do (it's just a small task), and downplay the risks (failure isn't all that bad). On some other projects, I might decide that my lack of motivation is a clue that I should just wrap up the project, get rid of specific tasks, delegate work, or transform those tasks into things I might enjoy more.

Rapid exploration: After I adjust for realistic expectations and get rid of tasks through ruthless elimination, I think of tiny tasks that will help me move towards my goals. That way, I can explore and get feedback faster. Then I try to get as much value as I can from those steps, usually ending up with blog post ideas and lessons learned in addition to the thing itself. This also means that I can squeeze work into 15- to 2-hour chunks instead of waiting for a 4-hour span of uninterrupted, energetic time.

There are a bunch of other things that help me out (keeping outlines of projects and tasks in Org Mode, documenting as much as I can, knowing my tools well), but those three behaviours above seem to be different from the way many people around me work. Hope that helps!

Kosio Angelov asked: “If you could use only three productivity tools for the rest of your life, which three would you choose?”

2014-05-14 Which three productivity tools would I use if I could use only those for the rest of my life #emacs #productivity

I'm totally cheating with my answers. I can't imagine using only three tools. What counts as a tool, anyway? Is the Internet a tool? What about the scientific method? Are we talking about apps, applications, platforms, systems, frameworks? =) Anyway, these are the answers that came to mind. They're not your usual suspects, but I'll explain why I like them a lot.

Emacs: This arcane text editor from the 1970s is capable of far more than most people think it can. It's not an application, it's a platform. I use it to code, write, plan, connect, automate, calculate, and so on. People get intimidated by its learning curve, but for me, it's well worth it. I've been learning and blogging about it for more than ten years. Based on what I've seen, I could probably keep going for decades. I love the way you can dig into how things work, tinker with the code to make it fit what you want, and combine different packages. Great user community, too.

I'm not sure what to say to productivity newbies considering Emacs. It takes a certain kind of person, I think. If you're someone who likes constantly learning and tweaking, you're good at learning from what other people have written, and you're not afraid to do a little worse in order to do even better in the future, this might be for you. You don't have to be a programming geek, although it helps.

Linux: Again, I'm cheating by including an entire operating system, and probably I mean all the little tools I've gotten used to rather than the operating system itself. But I love being able to use utilities like grep and find (thanks, GNU!), stitching programs together, scripting things, installing other tools… People have suggested that I look into Mac OS X, but it gets a little on my nerves. I like Linux more. There are some programs I want to run on Windows, though, so I end up using Linux in a virtual machine so that I can do my development in a proper environment.

Ruby:  I use Ruby for little automated scripts as well as special-purpose web-based tools like QuantifiedAwesome.com, which helps me track my time. It feels like the way my mind works. I used to use Perl for scripting and I'm learning Python, but Ruby has the least friction for me. This may change as I get deeper into other languages, but in the meantime, Ruby is a good language for the kinds of things I want to do.

—-

All of these tools take effort to learn. They're not like, say, Boomerang for Gmail or ScheduleOnce, which are easy to pick up and have clear benefits. My favourite tools require imagination, but they open up infinite possibilities. I'm not locked into one way of doing things. I still have limits, but they're the limits of my own ideas and skills. I think that's what I like about these tools. They have depth. Whenever I reach for some new capability, I almost always find it.

So, if you're a newbie and this sounds intriguing, how do you get from point A to point B?

I think I got here by being interested in learning, being unafraid of tinkering, and having the space to do both. When you're learning a complex thing, you might feel frustrated and intimidated by it. Good games design that learning experience so that people enjoy small wins as they develop their skills, but not all topics are like that. Sometimes you have to enjoy the learning for its own sake.

… which is an odd message to share with people who are looking for productivity hacks, maybe, but it's something I've been thinking about lately. There's a cost to picking general-purpose tools that are perhaps not the best at one specific thing, but experience results in compounding benefits. There's a cost to keeping both your schedule and your eyes open, but perhaps it can lead to surprising things. There's a cost to choosing the path of learning rather than the quick fix, but who knows what the true cost is down the road?

It's been twelve years since David Allen published Getting Things Done, with its geek-friendly flowcharts and processes for handling tasks in an interrupt-driven life. The way I manage my tasks is heavily influenced by GTD. I think in terms of next actions, waiting, and someday, and I have weekly reviews. I modified the TODO states a little to reflect what I need. It's time to think about those states again to see what I can tweak and what reports I could use.

I use Org Mode in Emacs to manage my tasks and my notes. I can customize it to give me different kinds of reports, such as showing me all of my unscheduled tasks, or all tasks with a specific category, or even projects that are “stuck” (no next actions defined). Thinking about my processes will help me figure out what reports I want and how I want to use them.

Here are different types of tasks and how I track them:

• Things I can work on right now (next actions): TODO
• Things that I can work on after a different task is finished: currently WAITING, but probably better to implement with org-depend
• Things I will revisit at a certain date, but I don't need to think about them until then: TODO, scheduled (I used to use POSTPONED)
• Things that would be nice to do someday, but maybe are incompletely specified or understood: SOMEDAY
• Things I have decided not to work on: CANCELLED
• Things I have asked someone else to do: DELEGATED
• Things I can ask someone else to do: TODELEGATE
• Things I am waiting for (usually not based on date) and that I need to follow up on: WAITING
• Things I can write about: TOBLOG. These are pretty optional, so I don't want them in my TODO list…
• If something is a duplicate of something else – remove TODO keyword and add link?

I use the following code for an agenda view of unscheduled tasks:

(defun sacha/org-agenda-skip-scheduled ()
  (org-agenda-skip-entry-if 'scheduled 'deadline 'regexp "\n]+>"))

(add-to-list 'org-agenda-custom-commands
   '("u" "Unscheduled tasks" alltodo ""
     ((org-agenda-skip-function 'sacha/org-agenda-skip-scheduled)
     (org-agenda-overriding-header "Unscheduled TODO entries: "))))

So the to-do process looks like this:

• Every week, review my evil plans and projects. Check my agenda without the routine tasks to see what new things I'm working on. Schedule a few tasks to encourage me to make regular progress.
• Every day, go through my Org agenda (C-c a a) and do all the tasks that are scheduled.
• When I'm done or if I feel like working on something else:
  • What do I feel like doing? If there's a specific activity that I feel like:
    • Go to the relevant project/section of my TODO list, or check the TODOs by context (drawing, writing, etc.)
    • Clock in on that task.
  • If there's a specific task I feel like working on:
    • Find the task, maybe with C-u C-c C-w (org-refile) and work on it.
  • If there's a new idea I want to work on:
    • Use org-capture to create the task, file it in the appropriate project, and then clock in.
• If I have an idea for a task, use org-capture to create the task and file it in the appropriate project.

How do I want to improve this?

• Maybe get more used to working with contexts? I have all these Org Agenda commands and I hardly ever use them. I tend to work with projects instead. Actually, working with projects makes sense too, because that minimizes the real context shift.
• Get better at reviewing existing tasks. I started tracking the number of tasks in each state (DONE, TODO, etc.), which nudged me to review the tasks and cross old tasks off. If I streamline my process for capturing tasks, filing them, and reviewing them by project/context/effort, then I can get better at choosing good tasks to work on from my existing TODO list.
• Estimate effort for more tasks, and use that more often I have some reports that can filter or sort by estimated effort. I don't use effort that much, though. Does it makes sense to get into the habit of choosing tasks by estimated time as an alternative approach? I usually have fairly large, flexible blocks of time…
• Tag things by level of energy required? I want to take advantage of high-energy times. So, when I feel alert and creative, I want to focus on coding and writing. I can save things like paperwork for low-energy times. I can tag some tasks as :lowenergy: and then filter my reports.

Hmm…

If you're like me, you probably have a to-do list several miles long. I like thinking of this as the backlog from agile programming. It's a list of tasks that I could choose to work on, but I haven't committed to doing everything on the list. This means I don't have to waste energy feeling guilty about not getting everything done. Instead, I can treat it like a buffet of projects to choose from depending on what I feel like working on.

2014-04-28 Dealing with an ever-growing backlog

I think I add tasks faster than I cross tasks out. (Hmm, I should track this!) It never ends. Most tasks suggest next steps I could take after I finish the first ones. You might think that an ever-growing to-do list is a bad thing. This is okay. In fact, this is good. It means that I'll always have a variety of tasks to choose from.

People manage tasks in different ways. For my personal tasks, I use several large text files in Org Mode for Emacs. Org Mode is an outline-based tool which makes it easy for me to organize my tasks into projects and projects into themes. It also supports tagging, links, agendas, dynamic views, and all sorts of other great ways to slice-and-dice my task list. Here's how I deal with some of the common challenges people face with a large task backlog:

• Making sure important, urgent tasks don't fall through the cracks
• Making sure you don't neglect important but not urgent tasks
• Keeping track of what you're waiting for
• Catching procrastination

I move as much as I can of what I know to the Web so that other people can use what I share. Added benefit: I can find things quickly! I use custom search engine shortcuts to help me quickly look up stuff. For example, I frequently refer to blog posts. I can type “b search terms” into my Chrome address bar to search my blog. Neat, huh? Here are the search engines I've defined.

Here's how you can define your own search engines:

1. Click on the menu button.
2. Choose Settings > Manage Search Engines.
3. Scroll to the bottom of the Other search engines list.
4. Add your own, one at a time.

%s will be replaced by the search terms from the command line.

Super handy!

Try setting up search engines for yourself. It takes a few minutes to set up one, and it makes searching so much easier.

Following up on sketching my goals: I've been thinking a bit more about goal factoring. What do I want to be able to do with an overview of my projects and goals?

• I want to make regular progress towards important goals, especially since I tend to move from topic to topic.
• I want to translate abstract goals into measurable projects, and I want to translate those projects into actions.
• I want to brainstorm alternative approaches that may get me to my goals faster, cheaper, or more effectively.
• I want to see which actions or projects can support multiple goals.
• I want to prioritize my projects and goals, putting things on the backburner as needed.

2014-03-24 How do I want to keep track of my goals #goal-factoring #planning #org

One of the benefits of writing down my goals is that I can look at the gap between plans and reality. An e-mail conversation with Daniel Reeves (Beeminder and the awesomely geeky Messy Matters) pointed me to the concept of akrasia, which is when you act against your better judgment (Wikipedia: akrasia; LessWrong: akrasia). In general, this happens because we value the present much more than the future. Short-term gains are more compelling than future ones. Immediate pains matter more than far-off sacrifices.

I haven't thought a lot about akrasia yet. If I can understand the concept and identify my akratic actions, then I can change my systems or try other tactics to live better.

2014-03-26 Reflections on akrasia – acting against my better judgment #rationality

• Sleeping: I could probably get away with sleeping less. That said, it's good (and uncommon) to get plenty of sleep, so this might not be too bad. I averaged about 8.9 hours a night over the past year. If I manage to tweak this to get, say, 0.5 hours more core time per day, that would be amazing. On the other hand, I could be the sort of person who really does need that much time, and it's still within the normal range. We'll see how sleep works out with my changing routines.
• Reading fanfiction during my commute when I could be reading nonfiction, learning Morse code, writing, or listening to podcasts… Actually, I've been doing more Morse code lately, so maybe this is not an issue. And I should probably have more mental downtime anyway.
• Being glued to my phone: On a related note, W- has teased me about my being occasionally glued to my phone. (It's funny when I'm trying to tidy up or make the bed one-handed.) This is more of an awareness issue.
• Not doing enough strength/flexibility/endurance: Biking helps me with lower-body strength, but my arms are weak. If I don't exercise to maintain my flexibility, I'll lose it over time. I have plenty of energy throughout the day, although I suppose it's good to build that up so that I have even more energy for bigger tasks. If I determine that mornings are the best time to exercise, then my lack of exercise is a combination of my desire to spend that time reading or writing (even though I already do this to the point of possible diminishing returns) and my dislike of how it initially feels to exercise.
• Socializing: I often don't feel like going out, although I conceptually know that connecting with people is a good thing. I suspect it's because I feel more connected with people around ideas instead of history or circumstance, and connecting to people over the Internet tends to more reliably result in good conversations like that compared to going to events or get-togethers in person.
• Crossing my legs: This is an awareness thing. I just have to notice it, and then I can gradually untrain myself. If I'm seated correctly, I'm fine. I tend to cross when I need a higher, slanted surface to draw on. More observations – maybe stochastic?

There are lots of other possibly akratic actions in my life. These came to mind first when I thought about things that I often do and that I can change when I pay attention to them. Still, looking at this set… I don't have a strong desire to eliminate akrasia while the suboptimal results aren't major hindrances. I'm fine with having a little slack in my life. Even when my actions diverge from my stated goals, I still learn a lot.

That's an interesting meta-thing to explore, though. Am I too comfortable? I've experimenting with moving away from carrot-and-stick approaches to personal productivity (or taskmaster and slave) and more towards appreciative inquiry (let's observe what's working well, and do more of that). Most people want to become more machine-like in their productivity, reliably following their plans. The contrarian in me is curious about alternatives. I don't know that life would be better if I worked with more focus or commitment. I know that it would be different, and there's a possibility that following the butterflies of my curiosity also creates value.

So let's say that akrasia (or at least how I understand it so far) tends to be effectively addressed with self-imposed deadlines, commitment devices, constrained environments, and so on. Writers sign up for NaNoWriMo. Entrepreneurs bet each other that they'll complete their tasks. Dieters remove junk food from their cupboards. These constraints support progress (by adding enough incentive to get people started or to convert downtime into productive time) or prevent backsliding (by removing temptations and distractions).

What are the trade-offs I make for not using these tools against akrasia? Are there ways I can turn weaknesses into strengths for those approaches?

Commitment devices are good for keeping you focused. If I let myself follow my interests, then I don't get to take advantage of momentum or compounding results. However, my habit of sharing along the way means that people can get value even from intermediate steps. Cross-pollination is valuable, too. On my personal blog, it's probably a good idea to have variety instead of focus, so that people can find what they're interested in.

Commitment devices are good for preventing backsliding. When you make undesired actions more costly (ex: eating junk food), you make desired actions cheaper in comparison (ex: nibbling on carrots). If I don't tinker with incentives that way, then I'll be more influenced by short-term effects rather than long-term effects. I am generally future-oriented anyway (ex: retirement savings, batch cooking) and I have fun connecting actions with long-term plans, so the disadvantages may be somewhat mitigated. I don't have a sense of urgency around this, either. Perhaps I need to exaggerate long-term costs in order to make this more compelling.

Things to think about…

Have you reflected on akrasia? Can you share your insights?