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.

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!

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!)

Still working on working on my own things.

Otio qui nescit uti . . .
plus negoti habet quam cum est negotium in negotio ;
nam cui quod agat institutumst non ullo negotio
id agit, id studet, ibi mentem atque animum delectat suum:
otioso in otio animus nescit quid velit
Hoc idem est ; em neque domi nunc nos nee militiae sumus;
imus hue, hinc illuc; cum illuc ventum est, ire illinc Iubet.
Incerte errat animus, praeterpropter vitam vivitur.

He who does not know how to use leisure . . .
has more of work than when there is work in work.
For to whom a task has been set, he does the work,
desires it, and delights his own mind and intellect:
in leisure, a mind does not know what it wants.
The same is true (of us); we are neither at home or in the battlefield;
we go here and there, and wherever there is a movement, we are there too.
The mind wanders unsure, except in that life is lived.

Ennius’ Iphigenia (~190BC), quoted in Wikipedia

I feel embarrassed to write about this because it’s such a privileged situation. “Oh, gee, whatever shall you do with your spare time? Gosh, I wish I had that problem! Now stop rubbing it in.” And I can imagine all sorts of quick answers I’d be happy with. I’m at least 80% happy with the solution of using my time to learn, code, draw, write, and share.

But there’s a question somewhere in here, and I want to explore it from time to time. I’m not sure what the question is, but maybe I can think around it so that I can sneak up on it.

What would answering this question look like? I don’t think I’ll get to the point where I’ll say to myself: “Aha, I have Answered This Question, and now I know how I should spend my leisure time for the rest of my life.” Hmm. No, I think I’m mostly looking for the feeling that I’m not making a huge mistake, that I’m not wasting my life, that there are people I look up to who have made similar choices.

Huh. That sounds promising. I think I feel more settled if I had more-developed mental counselors who’ve explored this type of lifestyle – something different from ambition and careerism, but also something different from private life or dissipation. The Wikipedia article on otium suggests people to learn more about, such as Seneca, Petrarch, Theophrastus, Aristotle, and Epicurus.

There’s also something interesting there about the idea of activities that justify leisure, lifting it up above idleness. Cognitio and contemplatio, studio and quies… (ref) And maybe both “contemplation and practical action” (ibid.).

So maybe there are three questions here:

• Who are the role models and companions who can guide me as I try to do this better?
• How can I improve how I use my leisure time?
• How should I feel about how I use my leisure time? Satisfaction reduces energy lost to frustration and opens up a relaxed way of thinking, but can also lead to wasted opportunities.

This reminds me of my post on Thinking about leisure activities: noble, advantageous, pleasant. Activities have differently-valued results. Playing video games sometimes leads to shared jokes and personal delight at the designers’ cleverness, but pales in comparison to other things I can do, so my LEGO Marvel Super Heroes languishes at 57.8%. Cooking results in temporary personal and familial value, but doesn’t benefit the wider world. Writing and Emacs geekery benefit a tiny niche, although sometimes I suspect that most of the benefit is personal rather than public.

Hence the temptation of consulting: clear benefit to myself (increased skills), my household (increased safety), and the team (increased capabilities), and possible benefit for tens of thousands of people.

And it’s also tempting to procrastinate the questions, focusing on easy answers like consulting and writing and geeking out about Emacs. They might be the sort of questions that resolve themselves, as my responsibilities and interests evolve. They might be the sort of questions that are easier to answer with more experience and skill. I’ve been reading about how the reasonable economic principle of ignoring sunk costs and focusing on marginal costs can bias established companies towards sticking with what they know, and it occurs to me that people are quite similar in this regard; the smooth groove of habit or expertise can be a rut that’s hard to get out of.

Hmm. I notice that some of the oddness comes from looking at leisure as work, as something to improve – to do more efficiently or more effectively. (This reminds me of this Yiddish saying: “Sleep faster, we need the pillows.”) If I want to, I can accept this attitude, managing myself with projects and timelines. But I’m curious about leisure as leisure, the thoughts you can think when you are unhurried. At the same time, there is this fear of being a slacker – the indolence of a couch potato or the isolation of an ivory tower.

So, something about people who set aside space for leisure, didn’t treat it like work, and yet accomplished useful things. This forces me to confront my definition of “useful.” What do I mean? An effect that lives beyond them. One could argue that spending time with friends or family can have diffuse results that outlive you, but I think I want something else in addition to that. Maybe to add to what we know.

And here something philosophical in me points out: “Why desire to be remembered? When you are dust, it won’t matter. Millions of people have lived and died without their names being remembered past a few generations.”

To which I say, “Okay, maybe it doesn’t matter that I am remembered, but it would be nice to know that something useful has been added.”

Then this inner philosopher says, “Were you waiting for a certificate? Here it is. You have done something that at least one other person has found useful. Whatever you leave undone, someone else will do, or it wasn’t needed anyway. How big of an impact do you need for your ego to be satisfied?”

And then I say, “Now that you put it that way, it doesn’t make that much sense. It’s one more thing to let go.” Slowly making progress. (The doubt pipes up again: “But should I let go? What if letting go is the wasteful thing to do here?” Tenacious, that thing.)

As for role models – I am not a special snowflake. There are countless people who live or have lived aspects of the life I’m figuring out. It doesn’t even have to be a majority-leisure life; I can learn from people who meditatively use the pockets of time they have each day. I can learn through habit and observation: instead of trying to think my way to the answers up front, I can try a little bit of this and a little bit of that, and I can reflect on the results.

It’s difficult to relax, but I’m learning.

Tom Morris' The Stoic Art of Living: Inner Resilience and Outer Results (2004) collects easy-to-read quotes from Seneca, Epictetus, and Marcus Aurelius. The author glues the quotes together with commentary, providing context and suggestions for interpretation.

I like the author's quotes from ancient philosophers, as other translations can feel stuffy. It's a decent overview of interesting thoughts, and you can follow the ideas to their sources. The book can feel a little light, though. There's something about the succession of quotes and topics that makes me feel like I'm bobbing up and down on a surface.

For comparison, I feel that William Braxton Irvine's A Guide to the Good Life (2009) goes into greater depth for fewer concepts. Ryan Holiday's The Obstacle is the Way reads more like a modern self-help book inspired by Stoicism, without as many quotes as this book.

If you've read a lot about Stoicism (and especially from the three philosophers featured here), you probably won't find a lot of new ideas here. However, you might pick up some good phrasings and ways to think about those ideas. As Pierre Hadot wrote in Philosophy as a Way of Life: “Ancient philosophy was designed to be memorized, so that it could be ‘at hand' when we are confronted with tumultuous situations.” Maybe you'll find the quotes in this book easy to hang on to. Enjoy!

If you want, you can check out the books on Amazon:

• The Stoic Art of Living
• A Guide to the Good Life
• The Obstacle is the Way
• Philosophy as a Way of Life

I get a small commission if you buy the books through those links, but getting them from the library is totally okay too. =) Have fun!