Category Archives: planning

Building tools for my future self

I was thinking about steps towards personal digital assistants. In a separate thread, I was also thinking about the psychology of aging. In a third thread, I was thinking about projects I might want to build to help me learn more. It makes sense to bring all these threads together: thinking of systems I can build to improve the quality of life I’ll enjoy in the future.

I think this might be a better fit for my experimental learning than either a hypothetical market or specific people. After all, I’ll always have a future self who could benefit. (And if I don’t, I’ll be past caring!) If the things I build along the way turn out to be useful for others, all the better.

Anyway, I was thinking about the kind of simple, deterministic, idiosyncratic assistant I could build to make life a teensy bit better in the medium term and the long term.

I could start with a text box interface on a webpage, then move to alternative inputs like dictation or neuro-integration(!) when that becomes reliable. It would be great to have some kind of offline buffering, too.

In terms of logic, I could start with stateless well-defined responses, add synonyms, support conversational interfaces, use weighted factors, add feedback mechanisms, and then eventually reach proactive notification and action. Inferences would be awesome, but I don’t have to wait for them to be sorted out. Ditto for program generation and adaptation.

In terms of sensing and acting, I can start with existing APIs and tools, write specific adapters for other sites, push into the physical world with sensors and actuators, use context and probability to simplify, and then take advantage of improvements in fields like computer vision or biometric analysis as other people build and commoditize cool tech.

But first, it starts with building a simple tool. Hmm, maybe a little thing that suggests what to do next (and coincidentally makes it easy to track)…

Future pull and the power of imagination

I know you’re supposed to live in the present, but I get a lot of value from thinking about futures and what I can learn from the possibilities. Imagining different futures helps me see what I can do, choose to do some things instead of others, and keep track of how I’m doing along the way.

In the problem-solving model that Tim Hurson shares in Think Better (2008), you come up with potential Target Futures and prioritize a few based on three factors:

  • Influence: Is it something you have influence over?
  • Importance: Is it important enough to you that you’ll put in the work to get there?
  • Imagination: Can you solve it with an off-the-shelf solution, or do you have to come up with something new?

A good future pulls you toward it. You want it, and so you act on it.

periodically think about what the target futures for my interests look and feel like. Last year, I wrote about how I don’t need to get to “awesome” in everything. Sometimes it still helps to think about what that “awesome” might look like, though. I realized that I don’t have to use the same definition of “awesome” that other people use. Figuring out what “awesome” means to me can help me identify the differences between my current state and my future state, and that shows me what I can do or what I can learn to get there. I want to pick differences that are mostly under my control, that are important enough to call me to action, and that may even create something new in the world.


2015-01-15 Imagining coding amazingly -- index card #wildsuccess #coding

2015-01-15 Imagining coding amazingly – index card #wildsuccess #coding

I figured out a little more about what tickles my programming brain. I’m not the kind of person who builds massively popular projects with elegant architecture. Someday I might do a good job at building bridges for other people so that they can do even better. What makes me really happy right now, though, is writing small, idiosyncratic pieces of code that are tailored to my particular needs (or that make things a little better for people I feel good about). On the surface, this doesn’t have widespread impact. but I guess it also creates a future-pull – showing other people that this sort of play and customization is possible. So, if I follow that vein, amazingness looks like:

  • Seeing clear, simple ways to address challenges or take advantage of opportunities
  • Pulling the pieces together (APIs, etc.)
  • Making reasonable interfaces
  • Writing decent code
  • Being proficient with tools
  • Getting good at that delivery and feedback cycle, whether it’s for other people or for myself

I’m getting a lot more practice in working with the APIs for services I frequently use. I’ve scripted quite a few small tools that interact with Flickr, and I’m looking forward to more experiments with Org Mode and Evernote. I’m also working on learning more about the tools I can use: debuggers, frameworks, even coding conventions.

Working out loud

2015-01-15 Imagining working out loud amazingly -- #wildsuccess #sharing #writing

2015-01-15 Imagining working out loud amazingly – #wildsuccess #sharing #writing

What about working out loud? What would that look like if I could do it really, really well?

I’d keep detailed notes – probably in Org Mode, since that lets me mix everything together: snippets, links, research, TODOs, etc. My notes would help me get back on track after interruptions or delays. Whenever I finish a small chunk, I publish a post, since that’s easier to work with than waiting until I’ve finished everything. I’ll know if it’s working if I:

  • don’t get as frustrated with dead ends, because I can just backtrack up the trail
  • can look up my reasons for things I’ve forgotten
  • can help other people find out about things they can do, take advantage of example code, or probe my understanding
  • get the occasional suggestion from people on how to improve what I do

I’m focusing on getting more of my thinking out the door. One of the things I’m currently figuring out is how to balance logical order and chronological order when writing up what I’ve learned. On one hand, I want to save people time by pointing them straight to stuff that worked. On the other hand, it can be useful to see the thinking process. I’m experimenting with using signposts (like the “later in this post” part of one of my write-ups). I’m also experimenting with harvesting tips and putting them into occasional other-directed posts.


2015-01-15 Imagining writing amazingly -- index card #writing #wildsuccess

2015-01-15 Imagining writing amazingly – index card #writing #wildsuccess

I don’t need to get to Pulitzer-prize-winning awesomeness. I want to get better at figuring things out and sharing them. I think this involves being able to:

  • wrestle with vagueness and beat it into specificity
  • share practical tips
  • extract ideas from research, other people’s thoughts, and my own experiences so that I can help people save time
  • and back up everything reliably!

If I can get better at seeing things, that’s a really useful bonus. Since the easiest way of doing that seems to be sheer accumulation of experience, I’m focusing instead on other things that I can get better at first. Research is one of those skills I want to build up again, as there can be lot of value in a good literature review.

2015-01-14 Setting constraints for my writing chunks -- index card #writing #constraints

2015-01-14 Setting constraints for my writing chunks – index card #writing #constraints

I’m also working on building up and linking to different chunks so that people can read at the level of detail they want. By setting constraints on chunk size and getting better at managing an archive of linkable things, I hope to be able to organize thoughts more flexibly.


2015-01-15 Imagining packaging amazingly -- index card #packaging #wildsuccess

2015-01-15 Imagining packaging amazingly – index card #packaging #wildsuccess

I imagine that as I get a sense of questions (other people’s and my own) and good sequences to answer those questions in, I’ll get better at putting together guides that lead people through those sequences. This helps because sometimes it takes a lot of knowledge to figure out what the next good question is or how to formulate it. For me, that’s what packaging is about: making sense of things, and then sharing that in a way that helps other people make sense of things too.

I’m still far from getting really good at this, but as I build up chunks and figure out what order to put them in, I’ll get better.

Your turn

When it comes to the things that you’re learning, what are different ways “awesome” could look and feel like? Are those futures powerful enough to pull you toward them? What do you need to do to get a little closer to those futures?

Trying on common goals

I’ve been thinking a lot about goals lately, thanks to a few discussions with friends. I don’t feel particularly driven by big, hairy, audacious goals (BHAGs). Instead, I focus on small wins and low-hanging fruit, accumulating progress. I don’t have a clear picture of exactly where I’d like to be in 40 years. Instead, I have a multiplicity of posibilities.

But maybe I’m not a special snowflake, and I can learn from the kinds of goals many people have. It’s fun to put on a different hat and try things out. By trying on common goals instead of rejecting them off-hand, maybe I’ll figure out more about what I really want and how to get there.

2015-01-21 What if I tried on common goals -- index card #popular-goals

2015-01-21 What if I tried on common goals – index card #popular-goals

Aristotle says that happiness is the ultimate goal.

2015-01-21 Playing with popular goals - Happiness -- index card #popular-goals

2015-01-21 Playing with popular goals – Happiness – index card #popular-goals

I find it helpful to think of happiness as a response to life instead of as an external state to pursue, so this goal feels a little odd to me. But it’s interesting to imagine a happy 90-year-old Sacha and what that life would be like. I think it involves building specific warm-and-fuzzy memories, maintaining a good perspective, and minimizing stressors.

Let’s take a look at other typical goals: wealth, power, fame, and knowledge/experiences.

2015-01-21 Popular goals - Wealth -- index card #popular-goals

2015-01-21 Popular goals – Wealth – index card #popular-goals

This might be the easiest of goals to desire, since it’s popular and measurable. Based on my reading, I imagine that conspicuous wealth will bring more problems than I’d like, so I don’t aspire to high-flying lifestyles. I value freedom, so it makes sense to have a financial buffer and to avoid becoming too accustomed to luxuries. That increases my security, which allows me to do more experiments. (I’m already privileged as it is!) Tools can be good investments, and it’s great to be able to strategically use money to make a bigger difference. Money also makes decisions easier: instead of worrying about cutting into your safety margin, you can try things out and see what happens.

2015-01-21 Popular goals - Power -- index card #popular-goals

2015-01-21 Popular goals – Power – index card #popular-goals

Power includes determining your life and influencing other people’s lives. I definitely care about having power over myself, but I’m not driven by the idea of making big decisions that affect thousands of people’s lives.

2015-01-21 Popular goals - Fame -- index card #popular-goals

2015-01-21 Popular goals – Fame – index card #popular-goals

I think I care more about depth of connection (tribe) than about breadth of fame (celebrity). I’m not sure about legacy. On one hand, it’s good to do things that are remarkable enough to help or inspire people throughout the years. On the other hand, what do we do that will matter after a century, and how can we get things to even be remembered for that long? I’ll think about this a little more while reading history. What makes essays resonate with me even after all that time, and how can I also reach across the years?

2015-01-21 Popular goals - Knowledge or experience -- index card #popular-goals

2015-01-21 Popular goals – Knowledge or experience – index card #popular-goals

I like the goal of learning more so that I can appreciate life better, maintain my independence, contribute meaningfully, and make better decisions.

I focus more on knowledge in the sketch above, but I think the popular approach to this goal is to focus on experiences. Bucket lists are practically all about experiences: seeing this country, climbing that mountain. That’s why travel is so big, I guess. What kinds of experiences would I like to have if I were to travel more?

2015-01-24 Thinking about collecting experiences -- index card #goals #experiences

2015-01-24 Thinking about collecting experiences – index card #goals #experiences

I currently don’t like traveling, but it’ll probably be less of a hassle now that I’ve gotten my Canadian passport sorted out.

2015-01-23 What would help me enjoy travel -- index card

2015-01-23 What would help me enjoy travel – index card

Still, with J- in school and three cats at home, it’s hard to plan. Maybe this will be something for later.

2015-01-25 On the other hand - travel -- index card #travel #learning #cooking

2015-01-25 On the other hand – travel – index card #travel #learning #cooking

Besides, I’m not totally convinced that travel is the best way to learn these things. It was fun being immersed in a language and going to local shops. But traveling to learn more about cooking seems a little wasteful, since airfare alone will buy lots of ingredients (and even personalized cooking classes). Staying home means I focus on cooking dishes I can enjoy long-term, and I can take advantage of our kitchen setup. So there’s an advantage to staying home, too.

What about other intrinsic goals?

2015-01-21 Popular goals - Health -- index card #popular-goals

2015-01-21 Popular goals – Health – index card #popular-goals

Health makes sense, since your enjoyment of many things can be curtailed by poor health. I probably won’t strive for buffed-up awesomeness, though. I’m mostly focusing on functioning all right, with maybe a little effort here and there to do a bit better.

2015-01-21 Popular goals - Meaning -- index card #popular-goals

2015-01-21 Popular goals – Meaning – index card #popular-goals

People want to make a difference at work and in their relationships. Many people feel that their work doesn’t matter a lot. Despite the abstraction of my work (I move bits around? I crunch numbers and questions? I write tools for a tiny, tiny fraction of the world?), I’m pretty good at convincing myself I have a small impact. =) Do I want to trade up by focusing on work that has a bigger impact (either for more people, or deeper in people’s lives? I don’t know yet.

2015-01-21 Popular goals - tranquility, equanimity -- index card #popular-goals

2015-01-21 Popular goals – Tranquility, equanimity – index card #popular-goals

I like this goal the most. Stoicism tells me that it’s the one thing under my control. It transforms the ups and downs of life into opportunities for growth. It doesn’t mean that I can’t enjoy things, I just shouldn’t get so attached to them that I become afraid. It doesn’t mean that I can’t be sad, it means I can try to take a different perspective on things.

Hmm. Trying on popular goals helped me take advantage of the collective centuries (millennia?) of thought that have gone into those goals. I still have to come up with my own specifics, but it’s good to be able to quickly test what resonates with me instead of trying to formulate everything by myself. If tranquility, happiness, and knowledge are my major goals (with health as the goal I know I should have), I can focus on coming up with specific ways I want to explore those areas.

Do you resonate with some common goals? What are they, and what are you learning from that?

Planning for possibilities

I like making contingency plans. It’s like peeking up a manifold of possibilities, imagining a sure-footed Sacha capably dealing with whatever comes down the pipe.

In preparation for a recent event, I made a list of different things that could go wrong, highlighting specific scenarios I needed to worry about and listing a few catch-all scenarios as well. Amusingly enough, the actual challenges that came up (Windows updates, network/hardware latency, a network configuration reset, Powerpoint crashes, last-minute changes) weren’t on my list as specific scenarios, but they were addressed by our general back-up plans. I like the blend of specific and general. Specific scenarios help you flush out questions to ask and things to prepare, while general scenarios identify characteristics to prepare for and help you come up with flexible strategies. Both types help you minimize stress when things do happen. Knowing that you have a backup plan, what the trade-offs are, and a probable deadline for committing to that plan helps you worry less about catastrophic failure and lets you focus on coming up with a better ad-hoc option.

One of the things that I gained a better appreciation of was the trade-off between preparing in advance and waiting until you can test your hypotheses. For example, I wasn’t sure if the server would be able to accept incoming connections once at the venue. I could adapt the code to run on my public webserver, but that would take a little time. However, since we were likely to be able to get things to work on the event network, I could postpone worrying about it to Sunday, which meant that I could spend Saturday doing non-work things instead.

Outside work, I also have a lot of scenarios and contingency plans. It’s been interesting slowly moving through time, watching the different uncertainties resolve themselves. Doors close and new possibilities open up. Because I’ve scanned my personal notes and I’ve blogged about many of my projections, I can recall a little bit of what past-Sacha was thinking, standing on the threshold of the unknown. I tend to overestimate risks and costs, but I’m good at coming up with small tests and approaches. I’m good at tracking my progress and keeping an eye out for “trip lines,” little reminders to myself to re-evaluate the situation. I want to get better at generating more general scenarios and alternative approaches, and properly evaluating risk/reward (maybe calibrating these with other people’s experiences). It’s fun treating life as a Choose Your Own Adventure where you might be able to peek ahead a little! =)

Things to do when you aren’t sure what to do with your life

“What should I do with my life?”

When you have the freedom to set your own TO-DO list, it can be difficult to decide what goes on it. Should you focus on one project or juggle a few? Why one goal instead of another? How much time should you spend on something new, and how much time on polishing something old?

It’s easy to get stuck in rumination. You can end up spending so much time and mental energy worrying about what you should do with your life that you don’t actually get things done.

Here are some things I’m learning about learning from constant progress and setting limits on second-guessing.

I keep a list of tasks that I can work on even when I feel the twinges of doubt. I organize this by project and type of task. For example, I feel like coding, I can quickly pick a task related to that. This means that if I don’t feel inspired, I can trust that the Sacha who made this list came up with tasks that would be a pretty good use of my time. It might not be the best use, but it won’t be a complete waste either. These unscheduled tasks give me a baseline of productivity. If I don’t want to work on something, I have to justify that by coming up with another task that would be even better.

For example, I know that I will generally get good value out of:

  • writing 1,000 to 2,000 words to answer a question or help people learn more
  • learning more about a specific programming language or platform by reading tutorials, source code, or blog posts, by working through tutorials, or by coding
  • writing tests and code
  • sketchnoting a video or book
  • exercising or cooking
  • braindumping thoughts

You probably have a list like that too: types of tasks that tend to work well for you, especially if they leave you feeling awesome.

Even a good list of tasks wouldn’t help much if I’m switching projects all the time. I’d keep getting started on different things, with very little to show for it. To deal with this second-guessing, I try to publish or share things as early as possible. That way, even if I switch focus, my notes are out there for other people to build on. This also opens it up for feedback and appreciation, which is great for encouraging me to work on something even more.

I also limit when I plan. During the week, I might decide to focus more on one project instead of another, but I don’t dump all my previous projects. If I come up with an idea I’m curious about, I add it to my list for later review. Every month, I look at my goals and evaluate my projects, checking which ones are still relevant. Every year, I look at my values and evaluate my goals.

When I catch myself procrastinating a task, I often use that as an opportunity to evaluate my projects and goals as well. Am I procrastinating because other projects have become more important? Great, I can replace the task with one for a higher-priority project. On the other hand, am I procrastinating because I overvalue immediate rewards over my long-term goals? The project/goal review reminds me why something matters and helps me get back on track. I don’t spend a lot of time thinking about whether I should come up with new projects instead. The time for that is when I review my goals and plan my month, not when I feel like procrastinating things.

Another thing that helps me box in my tendency to over-plan is reminding myself that I’m not trying to decide the absolute best thing to do with my time. Good enough is good enough. If I move forward, even if it’s not quite optimal, I can learn more than I would standing still. If I feel I’m slightly off-track, that can teach me about where the track is.


So it’s worth spending a little time making sure I’m pointed in roughly the right direction, but it might not make to spend four hours trying to figure out how I can get 100% instead of 80% value out of an afternoon.

It’s good to periodically check if I’m going the right way. I’m probably doing okay if:

  • I can tell how I’m different or what I learn week to week, month to month
  • My projects include several things that excite me, and I’m learning from my experiences working on different tasks
  • Other people tell me that what I share or work on is useful
  • Things build up; scale or network effects happen

If those are true, then I’m probably not wasting my time. I might even be able to get away without worrying about better ways at all. I can wait for people to suggest better ways to spend my time, and I can listen for suggestions that resonate with me.

What do you do to avoid getting stuck in the question “What should I do with my life?”

Related: Thinking about what I want to do with my time

Thinking about what I want to do with my time

Every so often, I spend time thinking about what I want to focus on. I’m interested in many things. I like following my interests. Guiding them to focus on two or three key areas helps me avoid feeling split apart or frazzled.

I balance this thinking with the time I spend actually doing things. It’s easy to spend so much time thinking about what you want to do that you don’t end up doing it. It’s easy to spend so much time doing things that you don’t end up asking if you’re doing the right things. I probably spend slightly more time on the thinking side than I could, but that will work itself out over time.

I balance thinking with moving forward. It doesn’t matter if I might be going in the wrong direction, because movement itself teaches you something. You discover your preferences: more of this, less of that. You get feedback from the world. For me, moving forward involves learning more about technology, trying experiments, making things, and so on. Taking small steps helps me avoid spending lots of time going in the wrong direction.

(And are there really wrong directions, or just vectors that don’t line up as well?)

What do I want to do with my time?

Fitness: The weather’s warming up, so: more biking, more raking, more compost-turning, more carrying water to the garden. It would be good to be fitter and to feel fitter. I like the focus on fitness rather than exercise – not exertion for its own sake, but practical application.

Coding: I like coding. Coding might be a perfectly acceptable answer to the question “What do I want to do with my life?”, at least currently. I’ve been doing a lot more Emacs coding, and I’m digging into other technologies as well. I like it because I can build stuff – and more importantly, learning helps me imagine useful stuff to build.

I think I want to get better at making web tools that are useful and that look good, but I’m not sure. Lots of other people can do this, and I haven’t come up with strong ideas that need this. (Back to the need for a well-trained imagination!) I can wait to develop this skill until I have a stronger idea, or I can learn these skills to lay the foundation for coming up with ideas. I’ve been thinking about getting better at working with APIs, but that’s even more like digital sharecropping than creating content on other people’s platform is. APIs, pricing models, and all sorts of other things change a lot. I’m wary of investing lots of time in things that I have very little control over.

What would a few possible futures look like? I could be a toolmaker, building lots of little tools for niche audiences. technomancy and johnw are great role models for this. I could be a contributor or maintainer, building up part of something like Org or Emacs, or perhaps one of the modern Web stacks. If I need to keep a path back into the workforce, maybe back-end development would be a good way to do that. I like talking to fellow geeks anyway, so it’s okay if I don’t focus on front end–that way I won’t have to deal with fiddly browser differences or client tweaks.

Writing: Writing helps me learn more and understand things better. It saves other people time and tickles their brains. It’s also a great use of my time, although sometimes I feel like coding has more straightforward value.

Lots of people write. I want to write about things things that are not already thoroughly covered elsewhere. I want to be myself, not some generic blogger – to write (and draw!) things that are geeky and approachable. I like writing about Emacs (goodness knows how we need more documentation!), self-tracking, experiments, technology, and learning.

What’s on the backburner for now, then?

  • Sketchnoting other people’s content: Useful and easy to appreciate, but potentially distracting from the other stuff I want to do. I may make an exception for books, since I like reading anyway.
  • Spreading sketchnoting: I can leave this in the capable hands of Mike Rohde, Sunni Brown, and Dan Roam. I’ll still use sketchnoting to think through things, though, and I’ll share them on my blog and on Flickr.
  • Spreading alternative lifestyles (semi-retirement, portfolio careers, etc.): Jeff Goins, Pamela Slim, and Mr. Money Mustache are doing fine with this. I tend to stay away from giving advice, and I don’t want to inadvertently feed wantrepreneurship as a substitute for actually taking action. I’ll still write about my experiments and decisions, though.
  • Spreading blogging in general: I’ll answer people’s questions and encourage people along, but I won’t dig into this as much as I could. I might make an exception for tech blogging, because I have a vested interest in getting more geeks to blog – more search results to come across and more posts to learn from! ;)
  • Drawing better: I draw well enough for my purposes, and I want to keep things approachable.

What does this reflection teach me about what drives me?

  • I like the feeling of figuring things out and of contributing to something that will build over time.
  • I like positive feedback, but I can move away from it if I want. For example, people always ask me about sketchnotes, but I like Emacs stuff more even though it’s hard to explain in regular conversation.
  • If I don’t have a particularly strong idea for something I want to build, I can spend the time learning more about the capabilities of the tools I use. Along the way, I’m sure to run into lots of small gaps. I can fill those in to demonstrate my learning.
  • I tend to build things for my own convenience. I open it up if I think a web interface will be handy, and if other people find it helpful, that’s icing on the cake.

For amusement, you can check out my list of back-burner things from October 2013. Back then, I wanted to focus more on drawing and writing. This time, I’m geeking out. Yay! =)