I've been thinking about how to respond to e-mails from former virtual assistants who are looking for additional work. I remember what it was like to feel that the world was a candy store of talent. My experiments with delegation led to interesting experiences. But at the moment, I can't really think of tasks that I want to specify or how much I would value someone else doing them.

Besides, I tend to get rid of tasks or write programs before I consider paying people to do things, so that tends to get in the way of delegation experiments. I find it more difficult to give instructions to people than to computers.

2015-02-03 Delegation and dreaming small dreams – index card #delegation

I tried thinking about ways I want to improve my life at the moment, and how I might want to accelerate those improvements. Compared to my answers from 2013, my current ideas feel closer to where I am, less of a stretch.

2015-06-12a Questions to revisit – index card #kaizen #experiment #delegation

Considering various ideas, I catch myself thinking, "Well, that would be nice to experience/be/have and I can imagine being happy with that, but I can also imagine being happy without that." I wondered whether that detachment came came out of avoidance or peace, and whether I wanted to tweak my balance of detachment and desire – ambition can also be quite a handy thing.

I know that a fuzzy brain dampens my ability to plan and anticipate. This is normal. I also know the fuzziness is temporary, so I'm not too worried about it. Still, I find it interesting to explore.

2015-06-12b Finding my own balance between desire and detachment – index card #stoicism #philosophy #detachment #desire

2015-06-12c Exploring this distance – index card #stoicism #philosophy #detachment #desire

On reflection, I think it's less about avoidance / running away from, and maybe more about not preferring something as much as I think I should. Consciously developing your preferences is an idea from Stoicism that I'd like to explore a little more.

2015-06-12d When I don't prefer something as much as I think I should – index card #stoicism #philosophy #preference

"Should" is a funny word, anyway. I avoid using that word with other people, but I sometimes still slip up and use that word for myself. So maybe it's more like I think it might be interesting if I had stronger, clearer preferences for things that were generally acknowledged to be good, but if I don't, that's more of an opportunity for learning than a personal failure.

In addition to general fuzziness, I think that gap happens when I have conflicting factors or motivations, and when I underestimate benefits or overestimate costs. I can untangle conflicting factors with reflection and honesty, even if sometimes that leads to uncomfortable realizations about my current self. I tend to overestimate costs more than I underestimate benefits, especially in terms of energy. In any case, my perception of one affects the other. I can work around this by giving things a shot, like the way skills often become more enjoyable the better you get at them.

Even when I have a good idea of the benefits and costs of different choices, sometimes it would be better for me to prefer things that have a lower short-term value than other things I could do.

A tangent: This might be pretty similar to how startups disrupt incumbent companies, actually. An incumbent company initially has lower marginal costs because of its investments. It would be more expensive for that company to shift to a new technology. On the other hand, a start-up doesn't have those sunk costs, so it's easier to invest in new technologies. Some startups succeed, getting to the point where they can beat the old technology in terms of return on investment. Other startups fail. But it's hard to tell which is which until you try, so it makes sense to have a bunch of start-up-like experiments even in larger companies.

2015-06-12e Thinking about disrupting myself – index card #experiment #disruption

So, what would it be like to use these tools to develop my preferences? There's the slow evolution of my preferences through reflection and incremental improvement. At the same time, it might be interesting to mentally budget X% of my time for exploring things even if I feel a little meh about them: not just "Hell, yeah" or No, but also things I still feel mediocre at. ('Cause you don't get to awesome without being mediocre first!) Doing those small experiments to play with my understanding and preferences might even be easier during fuzzy times than during sharp times, since my opportunity costs are lower.

I might keep my goals and experiments a little close to myself at the moment, focusing on elimination and automation rather than delegation. Maybe I'll branch out again when I have a little more brainspace to manage and train people, since I don't want to get to the point where I resent other people because of the consequences of my own mediocrity in delegation. In the meantime, little by little, I'd like to get better at understanding my preferences, and maybe shifting them ever so slightly.

I notice that even when I’m fuzzy-brained, there’s a part of me that observes it curiously. Even when I move slowly, tired, there’s a part of me that savours it. Even when it’s like there’s a big fuzzy blanket on my mind, there’s a tiny part that looks forward to being able to think about it.

I like having that little observer, the one who turns all sorts of things into learning experiences. I wonder how I can get even better at this.

In terms of drawing: Sometimes I feel a little odd circling around similar thoughts, like what to do when I’m fuzzy. But it’s okay to do so, especially if doing so clears away the surface thoughts so that I can notice little things to be curious about.

In terms of writing: If I have a bunch of posts scheduled, then I tend to skip writing when I’m fuzzy. But maybe that’s when I should write, so that I can remember what that fuzziness is like and dig into it deeper. There’s plenty of information out there already, so it’s okay for me to take some time to explore the things I haven’t figured out myself – even if they’re simple for other people.

In terms of learning: I like reading research. I pick up tools for understanding, and I can place my experiences within a bigger context. The more I read research, the easier it gets. I tend to be more interested in research than in popular science books or other non-fiction these days. Maybe it’s because the abstracts for research are so concise, and the occasional full-text article that I get to read goes into more detail than books usually do. Hmm, maybe I should learn more about the library’s research resources…

In terms of self-observation: Stoicism talks a fair bit about this. It might be interesting to make myself a reflection guide to use especially when I’m fuzzy. Even if it means reviewing the same thoughts, that should be fine. After all, the Meditations of Marcus Aurelius works well despite – perhaps even because of – the repetitive exercises.

What would it be like to have this part of me even further developed? I imagine being able to keep my calm in trying situations, and to appreciate life as it comes. I imagine being able to notice the tiny new things in each rotation. Even when I walk in circles, I can go somewhere new.

Since my childhood, my parents have always told me to follow my dreams. It wasn't just the usual maxim passed on from books and the child-raising culture of the time. I had proof of the power of dreams in the adventures of my father.

I talked to my parents last weekend. They're a little worried about me during this amorphous 5-year experiment with semi-retirement. Am I doing okay? Am I following my dreams?

At that moment, I realized that I'd found something that resonates with me even more than dreams do. I'm not following my dreams. I'm doing something stranger and more exciting to me. I'm experimenting.

I'd reflected on the difference between plans and experiments, and dreams are like that too. A plan has a certain end. A dream is a plan with passion and maybe a long-term story: "I've always wanted to…". There's that sense of certainty when you're following your dream. You know where you want to go, and you know what progress you're making towards it. You can feel it in every fibre.

I want something else.

I want the experiment. Uncertainty. Learning. I seek out in myself where the vision is still uncertain, where there's not enough data from other people's lives.

It's neat being able to trace my growth over time. In 2012, I became more comfortable with saying "I don't know." In 2013, I started letting go of the need for certainty, for clearly defined passions. In 2014, I found a metaphor that resonated with me: exploration. Now I know that I want this more than I want to check off boxes. I find myself the most curious about the things that are hardest to explain, going further away from common experience.

I could not have dreamed what I'm learning now. I'm well into territory that my younger self couldn't have imagined. I didn't know it was possible, then. Even now, I don't know the full range of possibilities. I'm not entirely clear on what awesomeness would look like. But I'm curious, and exploring is its own adventure. Wherever I end up, I'm sure it will be somewhere my present self can't picture.

I don't dream of being happy, and it's not something I pursue. That's is because I am happy. I see happiness as a deliberate response to the world: a steadfast focus on what's good about life.

If I strive for anything, it's equanimity. But even that is in my grasp as soon as I want it. Equanimity isn't a destination to arrive at. It's something to practice. Only time and trial can tell.

Aside from equanimity, what else is there to want? I'm as comfortable as I could be: roof, food, resources, tools, community, access to knowledge. Even those things are not essential. People have lived greater lives with less.

I don't dream of mansions or influence or fame. I don't need to wait for these things. Knowing that makes me free to appreciate and make the most of my current life.

I want a mind that takes everything as fuel. I want to turn both victories and obstacles into springboards. A thought: How can I intensify this experiment? How can I get better at learning?

• Reading and re-reading can help me identify role models, build on other people's wisdom, find the words to describe what I'm thinking, and combine interesting ideas.
• Developing practical skills increases my independence and enjoyment. Sewing, electronics, and woodworking might be good candidates to focus on.
• Writing and drawing might help me find people who resonate with these ideas. If I'm lucky, we might even explore them together.
• With self-care as a solid foundation, I can slowly grow outwards to encompass more within my circle of influence.
• To do that, I'm learning more about playing with the world: negotiating changes, developing relationships, applying energy and enthusiasm. We'll see how it turns out!

It's odd – I'm still not a big fan of uncertainty when it comes to physical space. Spur-of-the-moment road trips? That would drive me up the wall. I like having autonomy and being able to manage my levels of stimulation. But there are some kinds of uncertainty in life that have a different flavour to them, and that's what I want to explore.

Is this, then, my dream? It seems so different from the usual dreams that it's understandably hard for other people to understand. It feels constantly novel and evolving, instead of being a fixed North Pole for my journey. It is what it is, I guess, and I'll explore it while I have the space to do so.

One of my friends told me that he couldn't quite square Stoicism and what he knew about me. The general impression of Stoicism is, well, the "stiff upper lip" sort of stoicism, and quite a few people have told me that I'm one of the happiest and most optimistic people that they know. So I figured I'd write about it a little.

2015-04-20d What does Stoicism mean to me – index card #stoicism

I get my understanding of Stoicism from people like Epictetus, Seneca, Marcus Aurelius, the people who translated their books, and more recent authors like William Irvine. The philosophy was pretty similar to how I saw the world growing up, and reading about the ancient Stoics (and similar schools of thought) helped me flesh out those thoughts further because I could take advantage of other people's insights.

I really appreciated having inspiring role models, time-tested tools, and a wider vocabulary for recognizing and working with my thoughts. I liked the validation of equanimity as a goal in itself (not just pleasure or happiness). I found negative visualization and other Stoic practices to be really good at helping you develop appreciation and deepen your joy. I liked the sharp delineation between things you can control and things you can't, and the radical freedom and responsibility this helps you realize.

More about equanimity:

2015-04-03d Equanimity – index card #philosophy #equanimity

On a related note, this might explain a little bit about the wonder that fills my universe:

2015-04-20c The glass is amazing – index card #philosophy #perspective

Anyway, so that's how that works for me!

After RJ's recent party, I realized that my perception of and approach to small talk had shifted quite a bit from what it was a few years ago. In the past, I used to feel annoyed with how small talk conversations tend to cover the same ground repeatedly ("So, what do you do?") and how they didn't often result in follow-up actions or connections. Now I see small talk as a way to explore and appreciate other people's stories (especially since few people blog) and discover which aspects of myself might resonate with other people (and vice versa). It's also a lot of fun to play with the mental models that other people build up, which is why I've been experimenting with introducing myself as a housewife and then letting the conversations bring out other weird aspects. ;)

2015-04-19f Small talk shifts – index card #small-talk #growth

It's also fun building up little chains of stories with the kinds of hooks that make people say, "Wait, what?" Some examples of things that are incongruous or that provoke curiosity: semi-retirement, step-parenting a 17-year-old, combining laser-cutting and sewing, disassembling a washer/dryer, wearing a vest with an unusual number of pockets.

Weirdness is useful. Ideally, this weirdness brings out disclosures of other people's weirdness, or prompts them to connect me with someone else they know, or demystifies something and encourages them to explore it. As for me, I like finding out if someone is the kind of person I might want to get to know further – perhaps collaborate with or mentally model. I look for people with shared values, interesting experiments, and a sense of growth.

2015-04-19e Different worldviews – index card #small-talk

Experiments are good because we learn from the divergences. That said, sometimes I can be too weird – when something I do or something I experiment with is just too far from someone's worldview to relate to or understand. For example, sometimes I talk to people who just don't get Stoicism, simple living, homebody-ness, tech customization (especially Emacs), quantified/experimental thinking, or blogging.

That's cool. I don't need other people to validate me and I don't need to convert other people to my perspective, so it's really more of an opportunity to explore.

When people ask questions about one of my experiments, I've been leaving it up to them to drive the conversation since I'm happy to answer questions. Sometimes these end up in unproductive loops. It occurred to me that it might be fun to take a more sociological/anthropological approach to this: to deliberately explore other people's perspectives and dig into why they think the way they do, possibly from the position that I make perfect sense to myself and it's other people who are odd and deserving of study. ;)

2015-04-19d On talking to non-Stoics about preferences and value judgments – index card #stoicism

Here's a more detailed example. I talk about value judgments surprisingly often because people often press for information on whether I'd like to have kids, which I suppose is a standard small-talk question for women around this age. Harumph. They usually have strong opinions one way or the other. This is one of the things that I'm careful to not have strong value judgments around or be attached to specific outcomes for. Sometimes I use this as an opportunity to prod people to be more considerate about things by considering a wider range of scenarios. Sometimes I frame my response in terms of being happy either way. It's pretty rare to find people for whom this position makes sense. Many people are quite boggled by it. But I talk about equanimity anyway in case that resonates with someone who's been looking for that concept, and even if it doesn't sink in, I can rest in the knowledge that it makes sense to me.

On the other hand, my favourite kinds of conversations are with people who have deliberately cultivated their own differences from the mainstream and who can reflect on those experiments. Then our conversations become a high-bandwidth sort of brainstorming and swapping of notes. =) We might be doing different experiments, but we can understand and learn from each other's perspectives.

So, small talk. It's an opportunity to discover interesting things about people (captured in quick notes after the party, because who knows), play with sharing aspects of myself and messing up people's mental models, and learn more about things I do differently. Even when I'm talking to people who find it difficult to understand external perspectives or whose conversational skills are somewhat impaired by alcohol, I can pick up useful information about other people and myself. As I meet more interesting people and as those people grow through their own experiences, I trust that small talk will become even more fun. =)

The book that got me into Stoic thinking was William Irvine’s A Guide to the Good Life: The Ancient Art of Stoic Joy (2009). Stoicism resonated with me: the reminder that my perception of things is separate from what those things are; the acceptance that I can control only how I respond to life, not what happens; the awareness of mortality that belies the insignificance of our drama and sharpens the appreciation of our short lives.

When I went through popular translations of the source books like the Meditations of Marcus Aurelius and Epictetus’ Discourses and the Enchiridion, I found them easy to read, with a wealth of ideas to apply to my life. Since then, I’ve been on the lookout for more applications of Stoicism to everyday life. Naturally, Ryan Holiday’s The Obstacle Is The Way: The Timeless Art of Turning Trials into Triumph (2014) crossed my radar.

The book expands on the idea that you can view obstacles as opportunities, taking advantage of them in order to grow. Almost all of the thirty-two chapters (covering aspects of perception, action, and will) are illustrated with an anecdote or two, followed by some questions and advice.

I’ve sketched the key points of the book below to make it easier to remember and share. Click on the image for a larger version that you can print if you want.

Let me think about how I feel about this book so that I can get past the initial “Yay, another book about Stoicism!”

I came across a number of anecdotes I hadn’t read before, and I liked reading stories of more modern figures instead of just the usual old chestnuts. I didn’t find any new ideas that made me stop and think; if you’re familiar with the key works in Stoic philosophy, you probably won’t get as much out of this book as someone who is completely new.

It feels oddly like the book is about this relentless drive towards a goal, but that doesn’t quite fit with what I understand about Stoic philosophy or what makes sense to me. Maybe I’m misreading the book. To me, the freedom described by Stoicism isn’t about achieving great victories after much perseverance and resourcefulness. It’s about realizing that things are what they are, you can choose how to respond to them, and thus you always have opportunities to become a better person as you learn to work with nature instead of against it–even if the path you end up taking doesn’t look like what you imagined.

It’s hard to explain the feeling I get from the drumbeat of anecdotes all throughout the book, but let me pick a passage that evokes this difference for me. The introduction (page xiv.) has this:

To act with “a reverse clause,” so there is always a way out or another route to get to where you need to go.

I could be wrong, but I think this refers to the reserve clause suggested by Seneca:

The wise man never changes his plans while the conditions under which he formed them remain the same; therefore, he never feels regret, because at the time nothing better than what he did could have been done, nor could any better decision have been arrived at than that which was made; yet he begins everything with the saving clause, “If nothing shall occur to the contrary.” … Without committing himself, he awaits the doubtful and capricious issue of events, and weighs certainty of purpose against uncertainty of result.

Seneca, On Benefits – translated by Aubrey Sewart

I understand this to mean that Stoics make well-considered decisions that anticipate opposition, but also remember that achieving goals is beyond their control. It isn’t about getting to where you need to go. It’s about being a tranquil person throughout the journey, free from being too attached to the wrong things – including fortune or misfortune.

Maybe this isn’t a book grounded in Stoic philosophy as much as it’s a motivational book that springboards from a few Stoic quotes and concepts. This is okay too. It helps me understand what I agree with and disagree with in the book, like the way I agree with and disagree with parts of Stoic philosophy.

In terms of presentation, the book’s density of stories appeals to some people and not to others. I’ve become less fond of books packed with short anecdotes. An overdose of the modern approach of aesops every other page, the shallowness and patness of the tales? In a book about obstacles, it would have been nice to see deeper struggles, maybe even with normal folks instead of famous ones; stories of frustration and suspense and everyday things that people can relate to.

I’ve long internalized the mental shift suggested by this book–of transforming obstacles and frustrations into things that can help you–but if I hadn’t, would this book help me flip that mindset? Would reading it help someone who’s struggling with perspective – would it add much more value compared to giving them a brief summary of the book? I’m not sure. If reading about other people who had it worse than you and who still achieved greater things is the sort of information you need to pick yourself up and get going, this might be a good book for you.

But I doubt that’s the case for many people who feel stuck. We’ve heard the story that the Chinese word for crisis contains the characters for danger and for opportunity (wrong, apparently). Corporate language guidelines might suggest replacing “problem” with “challenge.” Coaches exhort people to reframe their difficulties positively, listing aspects to be grateful about.

When I run into my own challenges, it’s not because I’m waiting for the perfect story or maxim to break me out. I get stuck when I don’t take a step back and really see what’s going on instead of what I think is going on. I get stuck when I don’t have a handle on the problem, when I can’t grasp it, when I can’t break it down. I get stuck when I accept the current framing instead of coming up with creative solutions. I get stuck when I’m stubborn and not listening to what the world tells me. These are all points somewhat addressed by the book, but it seemed to lack something. Perhaps I need to read it more slowly, dipping in and out of it for reflections. Although if I’m going to do that, maybe I should sit with the classics instead.

Still, there are people for whom this book is a good fit, so don’t let this talk you out of liking it. If you’ve been curious about but intimidated by Stoicism, you might try picking this up. If you’re doing okay with challenges but you want to get even better at transforming them into stepping-stones, flip through this book and meditate on its points. (Although if you’re dealing with depression, it seems remarkably insensitive to tell you to just think of your problems as good things!)