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!)

Atul Gawande’s The Checklist Manifesto: How to Get Things Right (2009) emphasizes the power of checklists for improving reliability. Errors creep in when we forget things entirely or skip over things we should have done. In medicine, these errors can be fatal.

Gawande draws on his experience as a surgeon, the research he conducted with the World Health Organization, and insights from construction, finance, and other industries that take advantage of checklists to improve processes.

The book discusses ways to address the cultural resistance you might encounter when introducing a checklist. It recommends making sure that checklists are precise, efficient, short, easy to use, and practical. You need to develop a culture of teamwork where people feel that they can speak up as part of a team. You may even need to modify supporting systems to make the checklist doable.

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.

I like the reminders that you should design your checklists around logical “pause points,” keep checklists focused on the essentials, and treat people as smart instead of making the checklist too rigid.

The book distinguishes between “Do-Confirm” checklists, which allow experienced people to work quickly and flexibly with a confirmation step that catches errors, and “Read-Do” checklists, which walk people step-by-step through what they need to do. I’m looking forward to applying the book’s tips towards systematizing my sharing. For example, I’m working on a YASnippets in Emacs that will not only display a “Read-Do” checklist for doing these sketched notes, but will also assemble the links and code to do the steps easily. Sure, no one will die if I miss a step, but I think discipline and thoroughness might yield dividends. I also want to develop a good “Do-Confirm” process for writing and committing code; that could probably save me from quite a few embarrassing mistakes.

I’m interested in the diffusion of ideas, so I was fascinated by the book’s coverage of the eight-hospital checklist experiment the WHO conducted. The book discussed the challenges of getting other people to adopt checklists, and adapting the checklists to local conditions. Here’s an excerpt:

… By the end, 80 percent reported that the checklist was easy to use, did not take a long time to complete, and had improved the safety of care. And 78 percent actually observed the checklist to have prevented an error in the operating room.

Nonetheless, some skepticism persisted. After all, 20 percent did not find it easy to use, thought it took too long, and felt it had not improved the safety of care.

Then we asked the staff one more qusetion. “If you were having an operation,” we asked, “would you want the checklist to be used?”

A full 93 percent said yes.

There’s a comparison to be made between the reluctance of doctors to accept checklists and the committed use of checklists by pilots and builders. I came across a quote from Lewis Schiff’s Business Brilliant in this comment by Rich Wellman:

The following quote sums up the essential difference between a checklist for a doctor and a checklist for a pilot.

“How can I put this delicately? Pilots are seated in the same planes as their passengers. Surgeons are not under the same knives as their patients. To paraphrase an old joke, surgeons may be interested in safety, but pilots are committed.”

So checklists are a good idea when you’re dealing with people’s lives, but what about the rest of us? Checklists are good for catching errors and building skills. They’re also great for reducing stress and distraction, because you know that the checklist is there to help you think. That’s why packing lists are useful when you travel.

Already a fan of checklists? Tell me what you have checklists for!

Somewhat related:

• My new Google Hangouts on Air checklist
• Forgot my keys; automating memory

David A. Fryxell’s Write Faster, Write Better (2004) is a journalist’s collection of tips that might help you write faster. Fryxell focuses on eliminating waste: wasted research, wasted interviews, wasted notes, wasted words, wasted drafts. You can do this by organizing, planning ahead, keeping your focus in mind, and writing a good-enough draft the first time around (instead of revising loose drafts that run too long or circling around a never-finished perfectionist draft).

I’ve sketched the key points of the book to make them easier to remember and share. Click on the image to get a high resolution version that you can print if you want.

One of the things that I struggle with is that I often don’t have a clear idea of what I want to write when I start writing it. I don’t have a focused high-concept phrase that explains my angle and the surprise twist. I don’t have a clear outline that tells me what kind of research I need to do, who I should talk to, and how everything fits together. I don’t have an editor who’ll force me to come up with a clear concept.

Maybe I’ll get there with experience. It might be okay to do this kind of exploratory writing – a little like journaling in public – and then apply Fryxell’s techniques to extract and polish a chunk that would be useful to other people.

It seems almost given that you should follow your passion, but what if you don’t know what that is? Or what if following your passion prematurely can lead to failure?

In So Good They Can’t Ignore You: Why Skills Trump Passion in the Quest for Work You Love (2012), Cal Newport gives more practical advice: Instead of jumping into a completely unknown field to follow a passion which might turn out to be imaginary, look for ways to translate or grow your existing capabilities. Develop a craftsman’s mindset so that you can improve through deliberate practice. Often it’s not a lack of courage that holds you back, but a lack of skill. As you build career capital, you can develop your appreciation of a field, possibly leading to a clear passion or a mission. You also can make little bets that help you move closer to the cutting edge so that you can make something remarkable. This qualifies you to do greater work that involves creativity, positive impact, and good control.

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.

I agree with many of the ideas in the book, although I’m not entirely sure about the dichotomy that Newport sets up between passion and craftsmanship. Many of the passion-oriented books I’ve read encourage you to try out your ideas before making major changes to your life – for example, by working on your own business on weekends or by taking a second job. Very few people advocate leaping into the unknown, and if they do, they recommend having plenty of savings and a network of mentors, potential clients, and supporters. So the book comes down a little harshly on a caricature of the other side rather than the strongest form of the opposing side’s argument.

Amusingly enough, although the book describes What Color is Your Parachute as “the birth of the passion hypothesis”, I remember coming across the idea of gradually transitioning to a new field by first exploring something more related to your current one in What Color is Your Parachute, which recommends it as a way of lowering risk and clarifying what you want. I also remember the What Color is Your Parachute book to be less about impulsively following your whims and more about identifying and exploring the skills that gave you feelings of accomplishment.

Anyway, I think you start with curiosity. Then you develop a little skill. This makes you more curious, which helps you learn more, and so on. That–combined with feedback and appreciation–helps fan a spark of interest into a flame. So it’s not really that you start with passion or that you spend many years developing your craft before you can enjoy it, but rather that you gradually figure out both. (I have a feeling this somewhat agrees with what the book would’ve been if it weren’t trying so hard to distinguish itself from advice about passion.)

We just don’t normally express ourselves that way, I guess. It’s almost as if people are expected to either have strong convictions about their life’s work, or to be lost at sea. If you say, “I’m still figuring things out,” it’s like you’re a drifter. If you say, “I’m not passionate about my work right now,” it’s like you’re just going through the motions. I don’t agree with this, which is why I like the book’s emphasis on forming hypotheses about what you want to do, and testing that with little bets that also develop your skills. (This is particularly apropos, since J- will be choosing a university or college course soon.)

Anyway, after reading this book, the specific take-away I’m looking forward to following up on is that of exploring adjacent possibilities more systematically. How can I move closer to the edge of discovery in myself and in the fields I’m interested in, and what new areas have been opened up? I’ve been thinking about designing more focused projects that result in things I can measure and share. That’s similar to the middle layer of the pyramid that Newport suggests:

1. Tentative research mission – figuring out what you want
2. One-month exploratory projects with concrete results
3. Background results

On the whole, the book has a good message. You don’t have to love something to get good at it. Sometimes (often?) getting good at something will help you like it or even love it.

But the book feels a little… uneven, I guess? The anecdotes feel like they’re making too-similar points. The ones about failure feel unsympathetic and hand-picked for straw-man arguments. I imagine most businesses are not started out of the blue because of some grand passion. People prepare, they minimize risk, they work hard. Passion for something – either the work, the customers, or even just the life that’s afforded by the work – pulls them through the toughest parts and keeps them going. Sometimes they succeed for reasons unrelated to their skills; sometimes they fail for reasons unrelated to their passions. Sometimes things just happen. There are everyday businesses that don’t have the creativity, grand positive impact, or full control that are idealized in the book, but that still give people enjoyable lives. I think that the techniques and ingredients described by Newport in his book are good, but they are not essential to an awesome life.

On a somewhat related note, in the past few years, I’ve been learning to let go of the desire for either passion or mastery, Instead, I’m embracing uncertainty and beginner-ness, setting aside time for things I don’t quite love yet. It’s a challenging path, but it tickles my brain. =)

Anyway, if you’re looking for a counterpoint to the usual “Follow your passion!” advice and you want to check out So Good They Can’t Ignore You, you can check out this book.

Enjoy!