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! =)

“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

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! =)

Lucas Baker came across my Less Wrong meetup notes while looking for more information about goal factoring, a technique for analyzing your actions and goals in order to come up with better alternatives. I hadn't dug into it in much detail before, but since he was curious, I spent some time trying out goal factoring so that I could share more thoughts. Here are the resources I found useful:

• Sandy Maguire: Goal factoring
• Dee Stewart's templates
• Ben Kuhn's notes preparing for a presentation on goal factoring

I started by drawing different goals and their connections with each other. For example, I like learning more about tools and programming languages because that helps me build more tools and cool stuff, and that tickles my brain. It also gives me useful things to share, and that helps me make technical topics friendlier. Sharing also helps me connect with other people, which makes it easier for me to learn from different perspectives, which enables me to make better decisions. Many of my actions and goals support more than one goal, so I get a lot of value out of the time I spend.

I picked a set of goals and listed the actions that I frequently take towards those goals. I also brainstormed different actions that I could take or delegate. This was great because it helped me come up with more ideas for mini-projects or delegatable tasks. For example, a weekly Emacs tutorial might be fun and useful (and maybe I can even commission some of those). I can look into asking my assistants to interview me as a way of fleshing out particular post ideas, too.

One of the advantages of making a list of productive activities is that it's easy for me to switch from one good thing to another depending on my interest or energy. Since “Tickle my brain” turns out to be a totally acceptable goal (at least for me), I can give myself permission to spend one or two hours a day on tech learning. That had been neglected because of my focus on other activities. It's good to get back into tweaking my Emacs or learning more about NodeJS, though. I can get a little carried away doing this (flow can be dangerous!), so I limit my time. After about two hours each time (or maybe four, if I'm pushing it), I should resurface and check on the other activities I may need or want to do.

It's good to decide how much time I want to spend on other activities, too. For example, I want to work on delegation daily so that my assistants get prompt feedback and so that I keep filling the pipeline with more task ideas. I want to work on consulting enough so that projects and tasks keep moving, but I don't want it to take over peak creativity/attention time, so I move it off-peak whenever possible. Packaging (making PDFs and e-books, organizing and revising posts, recording and processing podcasts) takes time and isn't as engaging as the other activities, but it helps me connect with people, so I should do that weekly. I'll also see if I can delegate more packaging so that it gets done.

To make it easier to brainstorm delegation-related tasks, I pulled some out into a separate drawing. There's a lot of room for growth. =) I'm slowly getting used to having assistants do web research, and it turns out to be surprisingly useful. I probably read much faster than they do, but I benefit from the different perspectives and search words they use, and it's nice to ignore the fluff.

One of the templates for goal factoring encouraged you to analyze your current actions instead of getting lost in goals you think you should have. For my third attempt, I picked a few frequent actions and traced the connections to the goals they support. I brainstormed alternatives and compared the costs. The goals looked pretty similar to the first set, but a different perspective helped me identify other alternatives I can explore. For example, it might be a good idea for me to create a Trello board or update my public Org file with the things I'm curious about so that people can help me out.

What am I learning from this goal factoring exercise? It's a good excuse to brainstorm and examine alternative approaches for reaching my goals, especially in terms of identifying low-hanging fruit. I'm already used to explaining how my actions contribute to multiple goals and how my goals are related to each other. I occasionally talk to people about my big picture (or as I like to call them, my Evil Plans). The way I define my goals seems to be a little different from the way most people define theirs. Instead of having big goals and strong commitments, I have a lot of small goals with hardly any commitment aside from curiosity. This approach seems to fit me better, although I'm probably missing out on extra productivity. I like making lists of lots of little goals or possible actions, because that makes the low-hanging fruit easier to pick.

Reflecting on this led to exploring this metaphor of a buffet of goals. Influenced by Jim Collins' Good to Great, I set myself Big, Hairy, Audacious Goals (BHAGs) in 2005. “S.M.A.R.T.” was an even more common acronym for goal setting, and I tried those too. The meaning of S.M.A.R.T. varied. My mom's version was that goals should be Specific, Measurable, Ardently-desired, Realistic, and Timebound. (Specific, Measurable, Attainable, Relevant, and Timebound makes sense too.)

Time-boundedness was something that never quite caught fire with me, though. I think it's because I'd demonstrated “potential” at an early age (of the computer-whiz-kid sort), grown up with praise along the lines of “Wow, she can do all of this stuff and she's only ___ years old,” and nearly got caught up in the insecurities of looking over my shoulder or ahead of me at people who were doing even more awesome things at even younger ages.  I remember consciously deciding, sometime in my teens, that I didn't want age or speed to be special. People made a lot of fuss over precocity — but at the same time, it seemed that age became an excuse for them to not learn or try. I pushed back at that. I preferred looking up to late bloomers like Grandma Moses rather than the “30 under 30” lists.

Self-imposed time-based deadlines–“I will do ____ before I turn 35”–echoed that old conflict for me. If a goal was intrinsically valuable, I would do it already motivated by the knowledge that life is short (memento mori!); and if I wasn't motivated enough to do it, I didn't want to set myself up to feel like a failure just because I accomplished it at an older age instead of the goal I'd optimistically set.

So I've been moving away from goals with deadlines. I wrote a blog post about that in 2012, but I've been thinking that way for a while now, and I'm coming to a clearer understanding. I want to embrace my goals and move towards them as a whole, motivated person, not split myself into taskmaster versus slave. I want to move towards my goals out of interest and curiosity and wonder. Dates might work for other people, but not quite for me.

What do I replace that metaphor with, then? I think of having a buffet of goals stretching infinitely before me. I can choose the portions I want. I can enjoy a variety of tastes, textures, and cuisines. I don't have to overload my plate or stuff my stomach. I can graze. I can go back for more. As I nibble, I can think about what else I want to try, or how I want to tweak things, or if I want to rearrange the dishes for greater convenience. I like it. It's a fun metaphor. =)

So, coming back to goal factoring… What's next? More goal analysis! As it turns out, it's easy to combine Emacs Org Mode and GraphViz. I've started documenting my actions and goals in Org Mode. I hope org-babel will make it easy to slice the goals into different sets and produce intelligible graphs. You can check out the first attempt. It's very rough, but it will get better over time. =)

I have a lot of ideas, and it’s easy to get discouraged by the fact that I’m not making progress on as many of them as I want to. It’s simple math. If I make progress on two projects but let eight languish, I tend to feel guilty about those eight.

So I’m borrowing an idea from just-in-time delivery: the kanban method. The ideas are (according to Wikipedia):

• Visualize: See what you’re working on and where it is in the workflow. Also, keep track of where you’re approaching the limits.
• Limit work in process: My limit is probably two projects in focus. I work on one at a time. The other is there for switching to if I hit a snag or need to change things up. (See also: Managing Oneself) Everything else is on the back burner, the someday/maybe list, or the “nifty idea but probably not for me” list.
• Manage flow: I’m not paying much attention to this yet. It would be interesting to track how things move from current to back burner. I have some of that data through my timetracking.
• Make policies explicit: What gets a project onto my someday/maybe list, onto my back-burner, or into focus? There are lots of ideas that I’m happy to let other people explore; I pick up only projects that I’m personally motivated by and that I see value in. Of those, I identify which ones I can actually make some progress towards today. I focus on 1-2 things that I like the most (especially if other people want them too). I don’t stop myself from working on back burner things, but I no longer have to feel guilty about letting them lapse. If it turns out that I don’t actually spend time on back burner items in a month or two, that’s usually a good sign it’s a someday/maybe thing due to lack of present motivation or capability.
• Implement feedback loops: I haven’t paid much attention to this yet. Usually, people nudge me if I let some projects take too much of my attention.
• Improve collaboratively, evolve experimentally (using models and the scientific method): Tweaking my mindset to minimize guilt-friction is a good, small improvement. Looking forward to other small improvements!

Strict kanban would probably mean not even starting until I’d cleared off at least one work in progress, I think. I’m not that strict. I’m happy to switch back and forth, but it’s good to be clear about what I’m focusing on. That way, I don’t feel pulled in ten different directions.

Writing is my key project. Drawing, Quantified Awesome, and Emacs swap in and out of the #2 slot. Delegation tends to be more on the back burners. Someday/maybe? More business stuff, getting better at gardening, learning sewing, and so on. If I were better at delegation, I might be able to increase my capacity to do more, but it’s a lower priority at the moment (I appreciate the extra cushion that frugality gives me). I’m cheating with “Writing” and the books on my list – I’m planning to write them in short segments, one blog post at a time.

Knowing this helps because when requests come in for things that I’m not focused on, I can happily and guiltlessly refer them to other people. It makes decisions easier. Do I spend $X to attend a conference or course on Y? No, that’s on my someday/maybe list. It’s good to know what you can say no to in order to say yes to other things.

I might be able to make more progress if I focused on driving 1-2 things to completion, not switching them on and off the back burner. In that case, I would eliminate writing from my list of projects (it’s never done!) and move up the book projects. I tried that kind of intensive writing with Wicked Cool Emacs and it burned me out a little, but maybe I’ve learned since then. I like the interplay of interests, though. Maybe I can experiment with “week on, week off” patterns – there’s value in immersion as well…

Anyway, the point of this post is: I can’t do everything at the same time, so I’m learning to not stress out about it. =) If that’s something you struggle with too, then you might find that clearly identifying the things you are focusing on and gently letting go of the other things (at least for now) might help. Good luck!

It’s easy to get discouraged by the vague feeling that you’re ignoring lots of things that you wanted to work on: hobbies that fall by the wayside, projects gathering dust on your shelves, Someday/Maybe lists that grow and never shrink. I’m learning that thinking about what’s on your back burner can help you make your peace with it, deliberately choosing what you want to work on during your discretionary time and letting go of the rest.

I’m focusing on consulting this October and November. Assuming all goes well, December will be taken up by a vacation: wrapping up consulting, going on vacation, and recovering from the whirlwind. I’m going to be less “retired” than I thought I’d be at this point, so I want to be deliberate about what I’m putting on the back burner and what I should keep doing.

Consulting leaves me with one or two days a week when I can focus on other projects. I also have little bits of time here and there, and some time in the evenings. What do I want to fit into those opportunities?

Daily drawing: I really like this practice of thinking about ideas or questions on paper, and I plan to continue doing this. Since I’ve made it a warm-up and cool-down activity, I don’t need a lot of separate focused time for it. I draw to start and end my day, and I spend a little time filing new sketches. Decision: Continue doing this in small pieces.

Visual vocabulary: Someone asked me if I could share my visual vocabulary with people. I had figured out a good workflow for building my visual vocabulary using other people’s sketches, but I didn’t want to share my 1,000+ term collection because it’s based on other people’s sketches (copyright, you know!). So I started building a new visual vocabulary using only my own sketches. So far, I’ve processed all of my sketchnotes from 2013.

The next step is to process my personal sketches (including my daily sketches) from 2013, and then start going backwards in time. Although the work was simple and not challenging, it was a lot of fun reviewing my past sketches and remembering what the talks were about. Decision: I’ll spend a little time on this each week. I thought about outsourcing parts of it, but it’s probably going to be easier, faster, and more useful if I do this myself.

Topic-focused blog/book: I’ve been playing around with the idea of spinning off a separate blog focused on a small set of topics. The poll results were tied between learning/writing/notetaking/etc. and visual thinking/mind mapping/planning/etc., so I’m planning to focus on learning/writing/notetaking/etc. first because that will let me do all the rest even more effectively. Decision: I probably won’t split it off into a separate blog yet, though. I’ll use some of my daily drawing time to explore topics and flesh them out into a series of blog posts – possibly hitting two birds with one stone. =)

Quantified Awesome: I have bugs to fix, features to add, analyses to run… Well, the bug fixes come first. I’m going to set aside some of these focus days or weekends to get token authentication and a few other things working again. I’m curious about my groceries data now that I have more than a year of it, so I’m looking forward to crunching the numbers. Just how much rice do we go through in a year? How can we organize our space to allow us to stock up even better? Decision: Coding benefits from long periods of focus time, so I should use my free days for this. Once I get past the bugs, though, I’m okay with scaling back on this a little.

Server administration, learning new tech skills: My web server isn’t set up optimally. It’s probably slower and more conservative than it needs to be. There are configuration options I haven’t dug into, performance limits I haven’t tested, and so on. Still, my server hasn’t fallen apart recently, and it should be fine for now. Learning new programming languages, frameworks, or platforms might also help me in the long run, but that’s something I can guiltlessly postpone for this quarter. Decision: Postpone, revisit next year.

Delegation and automation: I keep wondering about how I might be able to take advantage of other people’s skills and experiences in order to learn more or do more, but I’ve been slacking off in terms of actually delegating things to people. I’ve been digging into why that’s the case (what are my excuses? am I missing some quick wins?), so you’ll probably see a blog post about that shortly. Still, I don’t want to delegate for the sake of delegating. I want to make sure that I specify work clearly and can pay enough attention to give good feedback as well as learn from the experience. This takes time and brainspace. I’ll dig into this if the opportunity comes up, but I don’t mind waiting until later.

As for automation, I’ll probably learn more about that on the way to doing other things. For example, AutoHotkey looks like it will repay further study. I’ll use some of my focus days to tweak things here and there, but I don’t need to push too hard on this. Decision: Postpone or do opportunistically.

Sketchnote lessons: This is where I teach myself (and other people!) more about sketchnoting by drawing different variants of common techniques. It helps broaden my visual vocabulary. I currently publish a sketchnote lesson every Thursday. If I make it less formal and more playful, I might be able to fold it into my daily drawing / doodling sessions. For example, I might try drawing people in different professions or in different situations as a way of expanding my visual vocabulary. This does require a bit more research, though, because I need to look at other people’s sketchnotes and reference photos. If I relax my expectations of publishing and make it, say, once a month, then I don’t have to worry about scraping the bottom of the barrel. (I should do one just about metaphors… =) ) That way, if I end up ramping up my drawing/doodling so that I have something publishable once a week or once every two weeks, that’s awesome. Decision: Scale back a little, and focus on doodling different categories?

Wrap-up

When I started thinking about what’s on my back burner, I felt a little overwhelmed. There was too much to fit into my week, not to mention the stuff on my Things I want to learn list that I haven’t gotten around to even starting. As I thought about what I could fit into small pockets of time, what needed more focus, and what I could postpone, things felt more manageable. Now I have a few things I can focus on, and I don’t have to feel bad about temporarily letting go of some of the things I was curious about. We’ll see how this works!

There will always be more things you want to do than time to do it in. You can get stressed out by your limitations, or you can exercise your ability to choose. Good luck!

It’s good to think about the kind of life you want to grow so that when everything comes together – knowledge, skills, character – you can make the most of it.

I recently turned thirty. This is great. Being a thirty-something carries a little more gravitas than being a twenty-something. It’s not a magic bullet, but I think it will help. Maybe in my thirties, I’ll get better at using the Voice of Authority. Maybe I’ll figure out how to stop sounding like I’m five years old. Maybe I’ll stop hedging my blog posts and conversations with maybes and probablys.

I checked the mirror the other day. Still no crow’s feet. Gotta work on those. Every so often, I think about the way I want my face to wrinkle and age. Smile lines, yes. Frown lines, anger lines, not so much. Do you think it would be weird to find someone who can retouch one of my photos so that I’m more crinkly? Usually people want to go the other way around.

Anyway. Growing older has its perks. While I wait for the aura of respectability to settle in, I’m working on accumulating knowledge and skills. They’ll come in handy someday.

I was going to say, this girl looks like she’s 16, what does she know? … but she says she’s 29. A little better.

from a forum post

I think it’s about deliberately growing my circles of authority: understanding my limits and then gradually expanding them. Here’s a snippet from a recent HackerNews article that made me think about this concept of “authority”:

3. I built a bigger product than I had authority for

I started up Happy Bootstrapper in April with no followers or authority. I planned to write a book about metrics first. The reason is simple – I know my metrics, but I’m not a growth consultant or a SaaS owner. Starting with simple info-products would have bought me time to grow my authority at the same speed with my products.

Then I just happened to stumble into a problem/pain that I knew I could help people with. I didn’t stop to think if I had the authority to actually sell the product. And if you aren’t selling something trivial then you’d better have something to prove people that you know your topic. Teaching people about the topic does the job, but it requires time.

3 Lessons From My Almost Failed Launch

Authority isn’t just for selling things. It can help when asking questions or sharing thoughts. It’s like the way open source mailing lists strongly encourage people to show their work when asking a question. Don’t just ask a question out of the blue, show how you’ve tried to find an answer on your own. Experience (even a little bit) earns you conversation.

It’s also about making it easier for people to identify with you, which is essential if they’re going to listen. I did a lot of technology evangelism as a consultant, coaching teams and communities on social business and internal collaboration platforms. It was always about finding a few people within the group or in a similar group with whom people could identify. Few people were going to listen to me say that something was easy to learn. In many cases, I was the same age as their sons or daughters, and they were used to being confused by stuff that their kids found easy. If the advocate was someone in their group – especially someone who’s not always the first adopter of new things – it was much more effective. One of the most useful techniques for influencing people is Feel, felt, found: I know how you feel. I felt that way when… I found that… You can tell it with other people’s stories, but it’s more effective with your own.

As I go through life, I’ll probably collect more experiences that can help me identify with people and vice versa. I’ll probably also diverge (like with this semi-retirement experiment thing!), but with experience, I can get better at emphasizing similarities. It’s the ethos of rhetoric’s logos, pathos, and ethos: character is part of persuasion.

And I’ll learn more, too. I’ll learn things worth sharing. I’ll learn things that can save other people time or money, make ideas easier to explore, and so on. Here’s what I’m a semi-authority on (based on what people have asked me about) and my current limits:

• Emacs: getting started, playing around with it, some coding – but not yet working with Emacs core or doing lots of Emacs Lisp wizardry
• Sketchnotes: getting started, working digitally, publishing, learning from others, using in presentations and blog posts – but not paper, and not graphic recording/facilitation
• Quantified Self: tracking time, analyzing data, working with Excel, basic stats – but not R, and only a few types of measures
• Blogging: learning through writing, blogging about tech and life, working with a large archive, adding sketches – but not yet e-books or other information products
• Bulk cooking: filling the freezer with individual meals (with an Asian slant), cooking frugally – but not vegetarian and not large-scale
• Hacking around introversion: connecting, taking notes, following up, speaking in public – but not networking events

I don’t want to turn into the “I know what’s best for you” sort of authority. I think good authority is more along the lines of being able to:

• empathize with people because you’ve been through something similar, and make it easier for them to understand where you’re coming from
• ask the right questions to help people think through things, share their experiences, and come to their own conclusions
• share experiences and pitfalls so that other people can avoid your mistakes or explore the secret bonus levels you’ve discovered
• enrich the conversation

What kinds of authority do I want to build?

I want to get really good at learning and sharing. I want to grok things and share what I understand. I want to inspire and help lots of people learn and share more effectively.

I want to get really good at working around my limits. That’s where Emacs, sketchnotes, Quantified Self, blogging, cooking, and introversion all fit in, I think. Emacs gets around the limitations of the tools I use. Sketchnotes and blogging help me get around the limitations of memory and introversion. Bulk cooking helps me get around the limitations of time. Quantified Self helps me get around the limitations of irrationality and forgetfulness. Not perfect, but useful.

I want to get really good at living life with equanimity. I want to weather the ups and downs and sidewayses of life. Frugality is a subset of this, I think – the ability to resist the temptations of consumption and desire.

So how can I build that kind of authority over the next few decades?

Primary insights come from doing things. As Washington Irving said: “One of the greatest and simplest tools for learning more and growing is doing more.”

Secondary insights come from reading, talking to people, and learning from other people’s lives. I can make the most of being close to a library and speed-reading like crazy. Decent fill-in while I don’t have much experience.

At some point in time, maybe everything will come together. I wrote once:

If I can get a decade or two of great writing out right around the time I should have tons of experiences to write about, that should be fine.

Quantified Awesome: Time and building mastery

Let’s see how this works out. =)

Image credits: Brain tree: Christos Georghiou (Shutterstock), Book tree: Cienpies Design (Shutterstock)

What kind of authority are you building? How are you going about it?