Category: The Obstacle is the Way

Practice Persistence

The most recent chapter in my continuing reading of The Obstacle is the Way is all about persistence and, to be honest, it’s exactly what you’d think.

The chapter starts with Ryan Holiday relating a story of General Ulysses S. Grant besieging Vicksburg. Challenges are enumerated, obstacles recounted. Distractions are mentioned. And, do you know what? Grant takes the town in the end, proving all the naysayers wrong.

The next story is of Thomas Edison inventing the lightbulb. You know that story, but it does include a cameo from Nikola Tesla, which seems worth recounting:

Nikola Tesla, who spent a fustrated year in Edison’s lab during the invention of the lightbulb, once sneered that if Edison needed to find a needle in a haystack, he would “proceed at once” to simply “examine straw after straw until he found the object of his search.”

The fact that that paragraph ends with “Well, sometimes that’s exactly the right method” pretty much sums up the whole message: get ready to work hard.

You can probably tell I’m a little sarcastic about the whole thing, partly because it seems cliché and partly because it seems like bad advice. (Some obstacles just won’t be overcome — you’re not going to head-butt your way through a concrete wall.)

However, later in the chapter, there is this paragraph:

Once you start attacking an obstacle, quitting is not an option. It cannot enter your head. Abandoning one path for another that might be more promising? Sure, but that’s a far cry from giving up. Once you can envision yourself quitting altogethr, you might as well ring the bell. It’s done.

I find that paragraph to be the most valuable of all that is in the chapter.

I guess that “work harder, not smarter” doesn’t seem like great advice. And, the “examine every straw” seems like the worst way to find a needle in a haystack. In fact, I think that we’re under an obligation to make the most out of the time that we have, and I think that if a certain approach isn’t yielding results, you have to start looking for the one that will.

(In an unrelated note, I seem to be happy to consider jumping between projects.)

I get the idea that you can’t give up too early, but I certainly think it’s just as wrong to never give up. Maintain the original objective, but be willing to rethink how you’ll get there.

More than simply saying “practice persistence,” I think it’s valuable to gain some insight into what kind of things you get better at with persistence (and what kinds of things just don’t get better, not matter how much you try and try) and how to benchmark, even informally, whether or not you’re making progress or just spinning your wheels.

So, my takeaway from this chapter is this: be persistent, but be willing to change what you’re being persistent at.


Get Moving

Continuing the ‘Action’ section in The Obstacle is the Way, this chapter is a call to action, and to a lot of it. It starts with a quote from my favorite President, Theodore Roosevelt:

We must all either wear out or rust out, every one of us. My choice is to wear out.

And continues with an anecdote of Aemilia Earhart receiving an offer to be the ‘token woman’ on a flight across the Atlantic. Though she wouldn’t be able to actually fly the plane and would be treated as ‘less than’ the men who did the flying, she swallowed her pride and accepted the offer.

The lesson is simple: she knew what she wanted to do, and making any kind of start at all was more important than her pride. We need to do more than swallow our pride: we need to say that, once we’ve identified the action to take, it’s time to get moving, even if it’s only an attempt or a symbolic gesture. Doing something is always preferable to doing nothing.

(I don’t know if I need to say this, but Ryan Holiday makes it clear in the text that “waiting for the perfect opportunity” is the same as doing nothing.)

Moving on to the story of the WWII German Field Marshall Erwin Rommel, the next lesson is that, once you’re doing something, anything at all, it’s time to do more.

Here, I don’t know how I feel about this. Sure, if you have Elon Musk’s overarching life mission, you need to be doing all you can to achieve it. But, if you’re balancing several projects with a family and a full-time job (I’m thinking of myself here), I don’t know that I can approach each project with an attitude of “how can I be doing more?” It’s a recipe for burnout.

So, for me, I think I’m going to be adapting this second lesson to be: don’t let any time in your life be wasted, know what you’re doing with it. If you need to recharge, recharge. But, if you’re just scrolling through Twitter because you don’t feel like writing a worksheet, it’s time to get started on that worksheet.

It seems as though my traditional closing to a post like this is to quote something from the end of the chapter, so let me do that here. I really enjoyed this (the beginning of the second-to-last paragraph):

We talk a lot about courage as a society, but we forget that at its most basic level it’s really just taking action–whether that’s approaching someone you’re intimidated by or deciding to finally crack a book on a subject you need to learn.

The Discipline of Action

We’re finally getting to the action section of the book. The perception section did seem as though it were getting repetitive, didn’t it?

This chapter starts with the story of Demosthenes, an ancient Greek orator who was orphaned young, had his inheritance stolen, was sickly… and went on to become a great orator. The story runs over a bit more than a page and is well told, but this paragraph sums it up:

Sure, Demosthenes lost the inheritance he’d been born with, and that was unfortunate. But in the process of dealing with this reality, he creted a far better one–one that could never be taken from him.

The first part of the chapter seems to be dedicated to one lesson: don’t feel sorry for yourself, get busy.

The second part of the chapter is less narrative (not as many stories) and more an inspirational speech for action, and, as the chapter draws to an end, for right action. (After all, action for action’s sake will most likely not work.)

[Fun aside, as I’m writing this, I’m waiting for SpaceX’s Falcon Heavy to launch. It’s been postponed, and in the meantime, I watched this video on the 5-year delay on the Falcon Heavy. One of the lessons I took from that video was the idea that SpaceX was wise to postpone the Falcon Heavy in order to take advantage of design improvements in the Falcon 9. It makes sense, and it’s the first thing that popped into my head when talking about right action.]

At the end of the chapter, right action is defined a bit more narrowly, and a rhetorical question is asked:

Therefore, we can always (and only) greet our obstacles

  • with energy
  • with peristence
  • with a coherent and deliberate process
  • with iteration and resilience
  • with pragmatism
  • with strategic vision
  • with craftiness and savvy
  • and an eye for opportunity and pivotal moments

Are you ready to get to work?

Isn’t that a great way to end a chapter? Why did I make the mistake of tagging a bit more on at the end?

An over-abundance of action, I suppose.

Prepare to act

It’s a bit funny that this is a ‘chapter’ in the book. And a whole page and a half, it’s more a segue from discussing perception to action. Because it’s so short, long excerpts would mean basically writing the whole chapter up.

Here’s the core message:

The demand on you is this: once you see the world as it is, for what it is, you must act. The proper perception–objective, rational, ambitious, clean–isolates the obstacle and exposes it for what it is.

And, that makes sense. After all, what good is seeing things for how they are if it just makes you apathetic.

I think what I like about Stoicism is that it requires action. We (I mean ‘I’) imagine a stoic person as a person who just sits there and takes whatever life dishes out, uncomplainingly. But, who needs a philosophy that reduces to “shut up and take it”?

Instead, a philosophy of “accept things for how they are, and then look at what you can do and do it.

When I’m rationalizing it in my own head, it’s like sitting down to card game every day and saying “what can I do to improve the cards I get tomorrow? Is it worth it? How can I play these cards to make the most out of today?” And then figuring out what needs to be done and doing it.

Finding the Opportunity

Continuing my The Obstacle is the Way reading, I was glad to get into this chapter, of only because it starts with WWII history. More to the point, we’re slowly finishing the section dedicated to perception and getting ready for the section dedicated to action (which fits: as I’m ready to incorporate a bit more action in my life).

The thesis of the chapter is simple: look for opportunity in adversity. But I love the fact that it starts with Eisenhower in WWII. After describing the German Blitzkrieg and some counter-offensives made after D-Day, Ryan Holiday says this:

Striding into the conference room at headquarters in Malta, general Dwight D. Eisenhower made an announcement: He’d have no more of this quivering timidity from his deflated generals. “The present situation is to be regarded as opportunity for us and now disaster,” he commanded. “There will only be cheerful faces at this conference table.”


By allowing a forward wedge of the German army through and then attacking from the sides, the Allies encircled the enemy completely from the rear. The invincible, penetrating thrust of the German Panzers wasn’t just impotent but suicidal–a textbook example of why you never leave your flanks exposed.

Fortunately, he goes on to name some situations that are closer to home for most of us than being a five-star general in the world’s largest conflict. One of my favorites was the idea of turning a job where you’re so miserable you could quit on its head by turning the job you’d like to leave into an interpersonal laboratory until you’ve got your next job lined up.

The chapter is long and full of other examples and wisdom, but that’s the core of it: when faced with an obstacle, learn to look for what you can get out of it, since you’re going to be enduring it anyway.

As seems to be a tradition, I’ll close with the last paragraph from the chapter:

No one is talking glass-half-full-style platitudes here. this must be a complete flip. Seeing through the negative, past its underside, and into its corollary: the positive.

Think Differently

Here’s a little thing you don’t know about me: I’m tired of hearing about Steve Jobs. I don’t know why, because I like stories from Elon Musk and his drive, but felt like the takeaway I got from the Steve Jobs biography was that people took it as permission to treat others poorly.

I say all that, because Steve Job is the focus of this chapter of The Obstacle is the Way. Better than Steve Jobs, though, is this quote that opens the chapter:

Genius is the ability to put into effect what is in your mind. There is no other definition of it.

-F. Scott Fitzgerald

I think that’s true. It’s what motivates me in my learning: finding the ability to make real (in some sense) the things I’ve only experienced in my mind.

The Steve Jobs part of the story can be summed up in these two paragraphs:

Steve Jobs was famous for what observers called his “reality distortion field.” Part motivational tactic, part sheer drive and ambition, this field made him notoriously dismissive of phrases such as “it can’t be done” or “we need more time.”

Having learned early in life that reality was falsely hemmed in by rules and compromises that people had been taught as children, Jobs had a much more aggressive idea of what was or wasn’t possible. To him, when you factored in vision and work ethic, much of life was malleable.

That seems to be the gist of the whole chapter: that a lot of our limitations are based on us having learned from an early age to be moderate in our expectations of ourselves and others. The lesson seems to be that we need to re-evaluate what we’re capable of and what we can expect from others.

Perhaps this will be the post that prevents me from ever being hired by “the next Facebook,” because I am not enamored of the “work seventy hours per week” startup lifestyle, and I believe in pushing yourself… but not in abusing yourself.

There is a story in the chapter about Steve Jobs telling his engineers that they couldn’t have an extra week to get something done… and the engineers eventually getting the project done within the initial time frame. And it’s framed as this great thing that Steve Jobs did.

However, I hear that and I think “those poor people’s families.” How much time at home did they miss? What are the chances that they were able to maintain whatever habits they had to keep their health and wellness up? What are the odds that any of them were the primary caregivers for their children? When their older, will they look back and think that moving a product a week earlier was worth the sacrifices they had to make?

I don’t know the answer to any of those questions, but I have a strong intuition…

So, in closing, this is from the next-to-last paragraph of the chapter, the same lesson stripped of the glorification of self-sacrifice:

An entrepreneur is someone with faith in their ability to make something where there was nothing before. To them, the idea that no one has ever done this or that is a good thing.

Live in the present moment

There is not a lot to explain about this chapter title in The Obstacle is the Way. So, I’ll jump to the first quote that jumped out at me further on in the chapter:

For all species other than us humans, things just are what they are. Our problem is that we’re always trying to figure out what things mean–why things are the way they are.

It’s true, and it’s something I think about often. I mean, I tell myself that a deer in the forest isn’t thinking about the looming Monday and returning to work… it’s just feeling safe or unsafe. (To be fair, the deer doesn’t have to go to work on Monday.  But also, its chances of dying of old age are worse than mine.)

The basic idea, the way I read this chapter, is to say that we shouldn’t have a programmed future, as that gives us something to measure ourselves against. Are we progressing towards that future? Is this moment the way we told ourselves it would be?

The book doesn’t say this, but I assume that there’s no indication that we shouldn’t make plans, only that we shouldn’t let those plans overwhelm us.

Something I like about this book is that the author, Ryan Holiday, makes some concrete suggestions:

You’ll find the method that works best for you, but there are many thigns that can pul you into the present moment: Strenuous exercise. Unplugging. A walk in the park. Meditation. Getting a dog–they’re a constant reminder of how pleasant the present is.

And, he goes on to provide one more great piece of advice:

On thing is certain. It’s not simply a matter of saying: Oh, I’ll live in the present. You have to work at it. Catch your mind when it wanders. Don’t let it get away from you.

When it’s not easy for me, it’s good to know that it’s not easy for anyone.