Category Archives: philosophy

Sketched Book – The Obstacle Is The Way: The Timeless Art of Turning Trials into Triumph – Ryan Holiday

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.

2015-01-05 Sketched Book - The Obstacle Is The Way - The Timeless Art of Turning Trials into Triumph - Ryan Holiday

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!)

Anyway, if you’re curious about the book, you can buy it from Amazon (affiliate link) or get it from your favourite book sources.

Like this sketch? Check out for more. Feel free to share – it’s under the Creative Commons Attribution License, like the rest of my blog.

A reflection on otium

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.

Sketched Book: The Stoic Art of Living: Inner Resilience and Outer Results – Tom Morris

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.

2014-12-10 Book - The Stoic Art of Living - Inner Resilience and Outer Results - Tom Morris

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:

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!

Categorical imperatives versus genetic algorithms

I was thinking about why I like thinking in terms of experiments, and how that’s related to how I generally don’t have strong disagreements with people.

I think most people I spend time with have a “live and let live” sort of policy similar to mine. We explore different life paths and have different opinions, but that’s okay. It results in more information and more insight.

Sometimes I come across people who express their opinions more strongly. Reading Reddit posts about people dealing with strong and probably well-meaning advice reminds me that there are people out there who are firmly convinced they know what’s good for you. I know I sometimes slip into that kind of advice-giving mode myself, especially around things that give me heebie-jeebies.

2014-09-12 Categorical imperatives versus genetic algorithms

2014-09-12 Categorical imperatives versus genetic algorithms

I like the idea that most of us are figuring things out in good faith. I haven’t thought through the limits of this idea yet (one’s choices might limit someone else’s, for example), but there might be something there worth exploring.

Appreciation and imagining loss

The Stoics have this practice of imagining loss in order to become accustomed to it and be less attached to these temporary things. You start by imagining that the loss of small things, and then move on to imagining larger losses like the death of a loved one. Seneca writes in his Moral Essays:

He robs present ills of their power who has perceived their coming beforehand.

and Epictetus advises in Discourses:

This is what you ought to practise from morning till evening. Begin with the smallest, the most vulnerable things, like a pot, or a cup, and then advance to a tunic, a paltry dog, a mere horse, a bit of land; next yourself, your body and its limbs, your children, wife, brothers. Look about on every side and cast these things away from you. Purify your judgements, lest something not your own have become fastened to you, or grown together with you, and cause you pain when it is torn loose.

You might think that this kind of meditation is depressing. I think it enhances my appreciation of what’s in my life, and thus contributes to my happiness. Reflecting on loss–or even non-existence–helps me appreciate how things and people have influenced me.

 2014-08-13 To know something's distinctiveness - #philosophy.png

Tangential story applying this to my life:

Actually, keeping my cool around cats and people is pretty easy. Probably the thing that I most need to practise patience with is Internet Explorer, as I occasionally feel annoyed and frustrated about it. (Not super-frustrated, but still pretty grumbly.) Maybe the next time I find myself peeved by cross-browser differences, I can remind myself of things to appreciate about IE. I’m sure the Internet would have grown slower without a default browser on lots of people’s computers, and IE keeps lots of people employed or consulting–all the things that need to be tweaked. And things are getting better now! At least I don’t have to code for IE6 any more, or even IE7. Besides, IE makes a good basis for humour. ;)

Philosophy. Not just for the big questions–also for the little tech annoyances opportunities to practise patience.

“Call no man happy until he is dead” – I think it’s okay to be happy

In a comment on my reflection on leisure, Thomas Worthington mentioned the story of Solon and Crœsus. Crœsus had asked Solon who the happiest person was, and Solon’s answers focused on people who had died admirable deaths. The idea is that you can’t say people are happy or blessed person until they die, since their luck could always go bad.

 I’d come across that idea before. Aristotle says something similar in Nichomachean Ethics:

He is happy who lives in accordance with complete virtue and is sufficiently equipped with external goods, not for some chance period but throughout a complete life. (1101a10)

It got me thinking about the differences between how I think of happiness and how I think they thought of happiness. I can see the point of those ancient philosophers, but it seems unnecessary to focus on what people would judge as happy.

2014-08-13 Call no man happy until he is dead - #philosophy

2014-08-13 Call no man happy until he is dead – #philosophy

For me, it’s much more useful and more real to be able to think of myself as happy, and to keep in mind that the ups and downs of fortune are small waves in a very deep lake. It’s like Louis CK’s rant, Everything’s amazing and nobody’s happy. I’m writing this on a computer and the text will be sent off through radio signals and electrons and photos around the world! And I have windows and indoor plumbing and all these other luxuries beyond those enjoyed by ancient kings.

But this kind of happiness comes easy to me, at least at this moment. We’ve learned a lot about how the mind works, but not enough – there are things that can take away your ability to appreciate and enjoy and hope. (Note to future Sacha: if this happens to you, remember that things will work out.) In the meantime, giving myself permission to be happy–not a tempting-fate sort of happy, just an appreciative sort of happy–makes it easier for me to enjoy life.

People have different ideas about happiness. Some people think happiness requires wealth, fame, pleasure, freedom. I doubt there’s much point in trying to change someone’s mind about happiness or get them to agree with you on your definition; and even your definition might change over time, as you learn from other people. Live your own life as well as you can. Perhaps by illuminating those possibilities, you might help other people explore their own.