Category Archives: stoicism

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.

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!

Stoic impressions: Weebles wobble but they don’t fall down

I’m with the Stoics rather than the Aristotelians on this one (or at least based on how I understand things): all you need for a good life is you. I’m not wise enough to know whether that’s true, but I think that it’s better for me to live as if that’s the case instead of thinking that happiness can be that much influenced by luck and external events. Challenge accepted!

I’m starting to understand what I’d like to aspire to be when I’ve infused whatever wisdom I can get from philosophy into my reflexive responses to life’s situations. I’m not trying to get through life completely unruffled and serene. Stuff happens. I get sad. I get excited. I get scared. I get delighted. I react to the world around me.

At the same time, I like this ability to step outside of these impressions. I can see myself even as I laugh or cry, working on separating the facts from what I think about them. I can enjoy the ups and downs and yet not get carried away by them. I can be happy that something I cooked turned out well and that people liked it; and I can know that in the grand scheme of things, it’s insignificant (but worth doing anyway). I can be scared about the possible downsides of something I’m going to try anyway; and I can know that in the grand scheme of things, it’s insignificant (but worth doing anyway). Something can happen, and I know that I could respond to it in many different ways.

Whatever life throws at me, I can choose to respond and not just react. Sure, the first few moments might be more instinctive–pain hurts, joy elates, sometimes I say the wrong thing–but what happens after that is up to me.

I’d like to avoid getting carried away by stuff, the way people get consumed by grudges or misled by temptations. I think that’s what the Stoics meant in their focus on ridding themselves of passions–not “passion” in the modern sense of “things I feel awesome about and enjoy doing,” but rather the kind of “passion” that takes over your reason and leads to suffering.


I guess I’d like to be like a roly-poly toy, like the egg-shaped Weebles of the slogan “Weebles wobble but they don’t fall down.” Then the Stoic idea of a passion might be wobbling so much and not quite being the shape that you need to be to bounce back, ending up so far off your center of mass that you stay down (or at least until other people help you get back up, because really, sometimes people do get wobbled more than they can handle, and that’s an opportunity for other people to help out).

So far, I’ve been extraordinarily lucky. It’s been easy to return to normal from the little things I’ve come across so far. You know how some video games are designed to gradually help you learn different skills and others throw you in the deep end? So far my life has been like the former. When things come, they’re within my range and I have the support structure that makes them easier to deal with. So I guess that’s like I’m playing a game where you get just enough wobbling so that you can correct your mass distribution or egg-shaped profile in order to wobble back better.

Which is sort of Stoicism, I think. Stoicism helps with adjusting so that you can deal with bigger and bigger wobbles if you need to. Stoicism reminds you that you are not the wobble that pushes you. You don’t control the wobble, so why bother stressing out about it? You can get better at bouncing back. You can work on becoming the weebliest Weeble.

I sometimes hear from people who are playing a much harder game, where they have to deal with pretty darn big wobbles before they’ve been able to sort things out. I’m not sure I have that much to offer. Newbie tips aren’t as useful for people stuck playing life on the “hardcore” setting, I guess! I can say that I’m working on being a better roly-poly toy and that it seems to be working out so far, but I definitely haven’t wobbled as much as other people have. But maybe reflections from someone living an easier version of the game can help people think about little aspects of their own games, either from the actual thoughts or even just the process itself.

One of the thoughts that helps me is this: wobbling’s what makes Weebles Weebles. So as much as I’m sure people wish for care-free lives, I’m okay with there being some wobbling in mine. I might not actively seek out really wobbly situations, but if they’re there, they’re there, and they can help me be better. Eventually, perhaps, experience will let me bounce back quickly from minor disturbances (or even ignore them entirely); and more and more things will seem minor, too.

In the meantime, wobbling away!

Simplifying with Stoicism: examining negative feelings

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.

Mapping a path to understanding Stoicism

Mapping a path to understanding Stoicism

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.

Exploring negative feelings

Exploring negative 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.

Recognizing potential fears

Recognizing potential fears

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.

Taking a closer look at the impostor syndrome

Taking a closer look at the impostor syndrome

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.

Extrapolating my futures

Extrapolating my futures

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.