Ancient Greeks hired philosophers to help their sons develop various skills, such as rhetoric and politics. I might not have that same kind of tutor now, but through books, conversations, and contemplation, maybe I can teach myself a little. It's like having an imaginary board of advisors with different perspectives that I can draw on, a technique that Napoleon Hill describes in depth in “Think and Grow Rich”.

It might help to ask myself; What are the life skills I want to learn, and which philosophers might be able to help me along those journeys? Let me take a look at some of the things I've already learned so that I can sketch out the next steps in that trajectory.

Equanimity: From Epictetus, I learned to focus only on what I can control: not what happens to me, but how I perceive and respond to that. I've also been learning about detachment from things I don't control. Why fear death? And if one doesn't fear death, why should one fear anything lesser? I'd already found it easy to take responsibility for my own happiness and outlook, but learning from Epictetus gave me a clearer way to see all those little decisions I make about how I see the world.

Self-improvement: From Aristotle, I'm learning to allow myself to use my leisure time to improve as a person. I occasionally worry that I should be spending this time building businesses and developing marketable skills, but I'm willing to experiment with Aristotle's assertion that philosophy is a worthwhile use of leisure time. I'm also learning that virtue is a muscle that you can exercise. As you get better at finding good activities that you enjoy more than activities that get in the way of your long-term happiness, and as you get better at wanting what's good for you instead of what's bad for you, virtue will become more natural. For example, I'm working on enjoying exercise and hanging out, and I'll work on appreciating art someday.

What else would I like to learn?

Getting along with people: I like this quote I came across in Bertrand Russell's The Conquest of Happiness:

“Fundamental happiness depends more than anything else upon what may be called a friendly interest in persons and things. … The kind that makes for happiness is the kind that likes to observe people and finds pleasure in their individual traits, that wishes to afford scope for the interests and pleasures of those with whom it is brought into contact without desiring to acquire power over them or to secure their enthusiastic admiration. The person whose attitude towards others is genuinely of this kind will be a source of happiness and a recipient of reciprocal kindness. … To like many people spontaneously and without effort is perhaps the greatest of all sources of personal happiness.

… The secret of happiness is this: let your interests be as wide as possible, and let your reactions to the things and persons that interest you be as far as possible friendly rather than hostile.”

I like a few people spontaneously, and others with some effort. If I can identify the things that are getting in the way of my appreciation of other people, use Epictetus' teachings to detach myself from those hidden fears and anxieties, and use Aristotle's exercises to eventually prefer things that are good for me, I think I'll be able to appreciate people more. =)

Developing a better appreciation of people is probably a good next step to focus on. It seems kinda weird to think of it as a skill to improve, but we take all sorts of things for granted (and our corresponding mediocrity as a given) when they're really skills one can learn.

How do I develop opinions? What is good to develop opinions about? How can I improve this process?

I've been working on teaching myself design. Good designs and bad designs both take effort to implement, so I might as well focus on good designs. I can read all the usability guidelines I want, but I need an aesthetic sense in order to bring things together into a coherent whole. Hence the need for opinions.

Lots of other areas benefit from opinions, too. Opinions can speed up decisions, save time and money, and help me appreciate subtleties. I'd like to form useful opinions while still being open to changing my mind in the face of good arguments or new evidence.

I don't have a lot of strong opinions. I tend to take things as they are, see the value in multiple viewpoints, and not get too attached to things. I can identify and let go of decisions that don't matter that much to me. In university, I nearly flunked my classes in literature. Art and music are still pretty opaque for me, although I do have a fondness for representational art and self-referential or otherwise punny music. Even when watching movies, I rely on IMDB reviews and TVTropes pages to shape my appreciation of what I'm watching.

W-, on the other hand, has a surprising breadth of well-informed opinions about things like kitchen knives, bicycle frames, and other areas. He has had quite a head start, though, so I don't feel too bad.

Anyway, I have a lot of catching up to do. I want to set some parameters on my opinion-forming, however.

• I want to still be able to enjoy simple things. I don't want to refine my palate to the point of feeling that I need luxury goods, particularly if this involves artificial distinctions instead of true value. So it's permissible to develop an opinion about different kinds of lettuce that I can easily grow or get from the supermarket, but I'm not likely to spend several hundred dollars on a brand-name purse.
• I want to be flexible in my opinions. I should be able to acknowledge situations where the opinion is inapplicable and consider alternatives.
• I don't necessarily have to have an original opinion. It's totally all right to follow other people's opinions. As much as possible, though, I'd like to be able to articulate the reasons for my opinions (even if I'm choosing someone else's position). In the beginning, I'll probably lack the words and self-awareness, but I'll get there if I keep explaining things to myself.

Okay. It seems that there are four stages in my opinion development:

1. Anything goes. No opinion on these things yet.
2. Do some quick research and pick a recommendation.
3. Go deeper. Compare several approaches. Critically think about them. Pick one approach or synthesize several.
4. Go a little further from the crowd. Come up with my own hypotheses and test them.

1. Anything goes: There are a lot of things I don't particularly care about. I'm willing to take other people's recommendations on them or follow my general principles. For example, I don't have a strong opinion about most of the ingredients we buy from the grocery store, so I usually pick the lowest unit price and then move up from there as needed. Decisions that have low costs (time, money, attention, risk, etc.) generally stay in this category, although I occasionally invest time in thinking about things based on the frequency of the decision.

2. Quick research: I read a lot, and I'm comfortable digging through whatever research I can find online. Many of my decisions are in this category. I do a quick search to see what other people are saying or bring up points from books I've read, and we use those ideas when choosing an approach. W- knows a lot about comparison shopping, and I tend to be the one with notes for communication, personal finance, and education. Sometimes I turn these into blog posts as well, especially if I can follow up with the results of applying that opinion.

3. Going deeper: Sometimes research doesn't turn up a clear answer, or I have to do the work in putting things together myself. I often request several books on the same topic from the library, reading them all over a couple of weeks so that I can see their overlaps and disagreements. Since it's easy to forget key points and it's easy to fool yourself into thinking you've made sense of something, writing and drawing help me a lot.

4. On my own: Some things are so uncommon, I can't easily find relevant research. For example, I'm not the only one who's done some kind of a semi-retirement experiment at an early age, but I don't think I'll find any books or online communities that already have reflections on all the questions I have. For topics where I'm on my own, I have to break things down into smaller questions that I might be able to research or test. Then I can write about what I'm learning, come up with ways to experiment, and share my reflections.

In terms of process, I tend to form most of my opinions by reading, writing, and trying things out. I rarely talk to other people in order to get their opinions about something, aside from the occasional people-related question where I'm curious about the approaches they've used. I don't debate my opinions since I'm hardly ever interested in arguing with people. There's no changing other people's minds, anyway; only presenting approaches and helping them change their mind if they want. Ditto for me – people might disagree with something I write about, but I'm more likely to acknowledge a difference in opinion than to change my mind unless I really want to.

So, what do I want to get better at forming opinions about?

I've already mentioned design as one of the areas I plan to focus on. Philosophy is another: forming opinions about how I want to live and what I will do. Developing opinions on exercise will involve trying things out and paying close attention to how I feel.

I could probably work on my opinions about business, too. Reflection might turn up more opportunities that are in line with my current interests.

In terms of tech, I can become more opinionated about good programming practices, patterns, and frameworks.

Some consumer things are probably worth developing more opinions about because of their cost or frequency in my life. It may be good to develop an opinion about bicycling.

Cooking is a good area for opinions, since it's all a matter of taste anyway. I can learn more techniques, get better at those techniques, and try different recipes. It might be good to develop opinions about gardening (particular cultivars? gardening practices?), although I'd probably need to develop the skills and infrastructure to start plants from seed first. Maybe start with salad green types? That'll have a faster growth cycle, and I can also test things by buying different kinds of greens from the market.

Do I want to continue with my current process? Are there ways I can improve it?

One easy step for improving my opinion-building process is to capture more of it as blog posts. If I write about opinions as I'm forming them, I benefit from the explanation and the review. Other people might be able to share tips, questions, or ideas. There are lots of little opinions and opinions-in-progress that I haven't shared on my blog yet. It could just be a matter of making blogging even more a part of my thinking process.

I can experiment with talking to more people while I'm forming opinions. I should probably be careful with that, though, since advice is a funny thing.

It might be interesting to be more explicit about the assumptions and hypotheses related to my opinions.

Hmm… Is this something you've thought about? How have you improved your opinion-forming processes?

Following up on my reflections on Aristotle, I've been thinking: what kinds of relationships can help me build a good life, and how can I help others in turn?

Aristotle distinguishes among relationships for utility, pleasure, or virtue. I have friends whose company and conversation are agreeable. There are a few whom I would go out of my way to help. I'd like there to be more of the last category. Getting to know acquaintances more will probably turn up a few, and I'll likely bump into more with time and familiarity.

I get along the best with people who are positive, self-efficacious, and temperate. I'm biased towards people who are confident and articulate. This probably means I'm missing out on appreciating otherwise awesome people. I feel a little odd and uncharitable that I don't feel that kind of appreciation about lots of people – I can wish them well and be nice to them, but there's something missing there. C'est la vie, I suppose. Something to work on from my end, or perhaps to accept. Anyway, Aristotle says it's quite rare to have good friends.

It would be interesting to have a lunch or dinner club of maybe six to eight people, meeting once a month or so. What kind of conversation would help us grow? Maybe something like “Here's what I've learned so far about life; here are the things I'm figuring out; I need help with this; I can help with that; let's make a difference in this; what did you think about that?” Different perspectives on the same things, similar perspectives in different situations… Many things are improved by conversation.

What would I bring to something like that, and to the individual friendships that comprise it? The basics might be location, food, organization. I tend to be cheerful, rational, and research-oriented. I'm getting better at sharing what I think, and at structuring and doing small experiments to learn. It might be interesting to connect with other people who like taking a step back, thinking about stuff, and then stepping back in and doing things.

If I found such people, though, would I share what I've been thinking about? I'm biased towards writing online instead, since the asynchronicity lets me think at my own pace. Online, I can reach more people and receive more insights. When I'm in conversation, I tend to listen to what's going on in people's lives instead of talking through what I'm trying to figure out. I prefer groups because of variety and lack of obligation (I don't have to carry as much of the conversation), but I also tend to step back even further into the background – I guide the conversation with questions instead of adding my own tidbits. So there's probably work to do there too. I wonder what a well-running potluck club would look like…

Hey, wouldn't you know it… There's actually a book called The Philosopher's Table: How to Start Your Philosophy Dinner Club. Requesting it from the library.

Anyway, how would I need to develop in order to bring more to and get more from conversation? It might be interesting to ask about my friends' lives, and share more from my life (more like “Here are some odd things I've been learning; maybe they'll be useful to you” rather than “me me me me”). I can practise that even without major changes. I can also invite people to things and check with them more often to see if they have plans. Maybe people might even be up for trying a few months of this dinner club thing.

What are the ends I pursue, and how do I pursue them?

I agree with Aristotle in that my ultimate end is happiness. For me, happiness is more along the lines of equanimity or tranquility: being able to appreciate the good parts and being confident that I can weather the tough parts. From stoicism, I understand that things aren't good or bad in themselves; it's more about my responses to those things. So for me, a good life is one where I can respond as I want to and as I should.

More specifically, what would that good life look like, and what are the goals I want to strive towards?

One easy goal to plan for is a good financial foundation. It's easier to act freely when you're not worried about food or shelter. I also work on keeping frugal, moderate tastes and a detachment from things. “It's just stuff,” W- and I say as we drop things off for donation or resist buying more things.

I value learning, too. I like feeling concepts click together, learning how to build more complex things. I particularly like it when I can use what I'm learning to save time, especially when I help other people avoid repetitive, mechanical work.

I enjoy learning and working the most when I can create something distinctive that takes advantage of an unusual combination of skills or experiences. For example, I like the social business consulting that I do because it's uncommon for people to be interested in large organizations, collaboration, workflow, change management, data visualization, programming, and design. I enjoy working on Emacs or on self-tracking because both lend themselves well to idiosyncratic questions and personal curiosities.

I've been self-consciously writing about leisure for what feels like too many days now. I'm trying to figure out how I want to spend my time, since that's a decision I'm going to make repeatedly over decades. My answers will change over the years, too, but if I think about it a little, I might be able to make better decisions.

Most of the time, we think of relaxation and recreation as ways to recharge ourselves so that we can get back to work with more energy. Aristotle prizes the contemplative life, where you use your leisure time not just to amuse yourself, but to improve.

What does that mean to me, though? For example, I could spend some time learning languages, or developing my drawing skills, or picking up a new technology. There's so much more to learn about all sorts of other subjects. An easy answer to the question “What shall I do with my time?” might be to volunteer, but I would also want to do that with deliberation. What will help me grow, and what's just a nice-to-have?

Let's say that I don't know enough to choose those topics from the beginning. How can I get better at observing myself and learning from how I use my leisure time? What would make a difference when I look back over a long life?

One of the things that has helped me a lot and that I'd like to get very good at is the ability to notice (as the Less Wrong community phrases it) that I am confused, and to explore that confusion. Reading helps me notice the gaps and find words to describe things, and writing helps me start to untangle the knots. If I keep getting better at this, then when I'm much more experienced, I might be able to spot opportunities for growth, catch myself before I make mistakes, and also help friends think through their own lives.

Learning various skills (tech, DIY, cooking) helps improve my self-efficacy. I can make more things myself, and I can imagine more things too. Besides, it's fun, and occasionally economically useful.

I'm still not as keen on conversation and friendship as I probably should be, at least according to Aristotle. I enjoy conversations with W- most of all. I like the mix of practicality, growth, and whimsical puns. On occasion, I enjoy conversations with other people, especially those I think well of and want to support. Other times, I talk to people for variety and social exercise. I'm comfortable with that because I'm not trying to be popular, entertaining, or entertained. I don't mind taking my time with the slow collection of interesting people I can learn from and help.

I can use my leisure time to learn how to prefer things that are good for me. For example, I'm working on that exercise habit. I'm sure that once I've gotten into the swing of things, I'll be able to enjoy it – I just have to stick it out until then. I have much to learn about music, art, design, and literature, too.

I think a good life is one where I have the space, awareness, and control to respond to life the way I want to, and that I've learned to want what's good for me. I'd like to be able to say, looking back, that I've deliberated on how I wanted to live and that I've lived pretty darn close to what I decided. We'll just have to see how it all works out!

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.

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.

• 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?

It’s really easy to get caught up living someone else’s dream. It makes sense to want what other people want. You see the visions that other people paint for you and say, “Yes, that looks pretty good.” Sometimes being influenced by other people can be very useful. We surprise ourselves by reaching goals that we didn’t even know that we could try. Other times, we drift away from what matters to us. This is why it’s important to check in with yourself once in a while to make sure that you’re still going towards your dream.

I’m a person of small and simple dreams. I want to have enough, to know that I have enough, and to know that whatever I have is always enough. Of these three things, I think the last is the most important. After all, people do well with more and with less, and people do badly with more with less. Reading all these books about stoicism reminded me that having enough is one power that we always have, no matter what our situation is.

I’ve been thinking a lot about the motivations and values that underlie my questions. Safety is surprisingly important to me. I plan for different scenarios, and I look at other people’s lives to get ideas for mine. I want to make good decisions: decisions that consider the true range of choices, take potential consequences into account, and leave me with enough space for both mistakes and opportunities. With the basics taken care of, I can focus on doing well. Knowing my tools helps me make the most of them. Learning from other people and sharing what I know helps me grow. I like taking advantage of low hanging fruit, the little things that I can do to move things forward.

Just as motivations are behind questions, values are behind motivations. What do I value? When does my life feel like it’s consistent with who I am, and when does it feel inconsistent? I really like exploring the things that make me curious, especially if they lead off the well-worn paths. I like helping people learn. I like building things: a good home life, tools, processes, knowledge.

What kinds of questions can you ask yourself to check if you're following your dream, not some dream that other people have given you?

The more I can master myself, the less I need, and the freer I am.

I dug into a collection of Epictetus' discourses to learn more about Stoicism. While I've never been much worried about death and I'm unlikely to run into issues with jail, exile, or hemlock (!), I have a lot to learn about dealing with aversion and negative emotions. I live a happier and luckier life than most people do, and I wonder what it would be like with even more understanding.

How can I learn more about this through practice? I can start with negative feelings, then move to attachments, and then get even better at understanding what I do and don't control.

When do I feel negative emotions? What situations disrupt my feelings? Mostly these emotions are directed at things or at myself: frustration with . I'm getting pretty good at not being perturbed by people, even though sometimes other people think I'm annoyed with them when I'm more annoyed with the situation. That said, I'm becoming less inclined to do the emotional work of reassuring people that it's not about them, so sometimes I just take responsibility for what I can control and let them be responsible for their feelings.

Hmm. Frustration and annoyance tend to be outward-directed, while anxiety and embarrassment are internal. I can deal with frustration and annoyance by accepting that the world is what it is. Anxiety can be addressed by faith that things will work out, and embarrassment is just ego in disguise.

So what are those anxieties about, anyway? Let me dig into those further.

Come to think of it, there's not much to be afraid of. I don't have to worry about missing out. Life is pretty darn good even like this, and the rest is icing on the cake. Likewise, I don't have to worry about falling short of expectations, since proper expectations are other people's responsibilities. Messes and mistakes can teach me a lot. As for the fear that pressure or other forces might sway me into making bad decisions… Being able to recognize the warning signs will help me slow down, and mistakes are good for learning anyway.

The fear of falling short is at the root of the impostor syndrome, something I've written about a few times before. I remember reading about the impostor syndrome when I was in school, and recognizing myself in it. You might think that the validation of programming competitions, newspaper articles, and personal projects would boost my belief in myself, but that often made me feel even less like the image I thought people had of me.

But the impostor syndrome, too, might be ego disguised: part desire for validation, part aversion to embarrassment. If I can let go of both, I'll be more free to concentrate on the things worth thinking about, and I can take better risks. So out to the curb they go.

As for the fear of missing out, of not quite doing enough… I've been thinking about how to learn more and how to increase the difference I want to make in this world. In particular, I want to get better at learning from people, which includes learning from coaches. I hear coaches are good for accelerating your growth. I'm careful about how I frame this to myself, because it's much too easy to become unhappy with how you're growing and to want more, more, more.

I realized that I could actually get a pretty good sense of what my life might look like in thirty to forty years, even if I continue in my current trajectory. My parents are in their sixties and I have other mentors around that age, so I know roughly what to expect. Assuming that my skills and tools stay roughly the same, I'm probably going to end up with an even bigger archive of ideas and notes. However, I already know what it's like to have more notes than I can remember and more sketches than I can grasp. Even if I continue with the same strategies, things will probably already be wonderful. If I learn from experience, adapt to the changes in technology and society, and explore new ways of doing things, then it will be even better.

This means that I can probably let go of the fear of missing out, of not living up to my potential or not maximizing awesomeness. Life is already wonderful.

I like thinking through this in advance, when I can reason about them with a clear mind. When situations come up, at least I'll have rehearsed some options. The real tests are when I'm tired or hungry or sleepy, or when something major happens. We'll see. =) In the meantime, it's good to look at the things I might unconsciously avoid looking at, to see what I can do to let them go.