Prepare for none of it to work

After writing up a pretty ambitious plan — to jump up two levels in my personal social hierarchy — it seems like this is a good time to reflect on the possibility of failure. This is a chapter in my continuing The Obstacle is theWay writing project.


This is a short chapter. Two pages. It could easily be one if there weren’t so much whitespace. Still, it includes an important message: things might not work out.

It begins with a quote from Seneca:

In themeantime, cling tooth and nail to the following rule: not to give in to adversity, not to trust prosperity, and always take full note of fortune’s habit of behaving just as she pleases.

Some things are out of your control. Fortune is a fickle goddess and cannot be forced by any measure of willpower to bend to our desires. Some things go wrong.

In this chapter Ryan Holiday points out that we can use failure as an opportunity to practice other virtues, such as humility. But, that doesn’t seem like it would make me feel better. I can’t imagine myself looking at the ashes of a project and thinking “well, at least I get to practice humility.”

My relationship with failure

In my heart, I’m a kid to whom things always came easily — or not at all. I was a good student and got a great SAT score without studying. My grades were fine and I got through college on my ability to read and be curious about anything. There was not much hard work involved.

In fact, the first time I really invested hard work over time — learning German — was more about proving something to people who thought I couldn’t do it. Even now, I can remember the feeling when I realized that my German was not bad, and that nobody but I would really appreciate the hard work and willpower that went into it.

It was a good feeling, and I liked to know that I had that in me.

Of course, I didn’t tap into that ability again for a long time. I made it through the National Guard based on an attitude of ‘do the minimum, but do it cheerfully’ and college was not super hard.

Not until I decided to get in shape did I need to remind myself that I had capacities that I had hidden away from the world.

Hidden is a good word, because I’d grown up with the philosophy of “if at first you don’t succeed, destroy all evidence that you ever tried.” Don’t let people see you fail, and they’ll think you’re a wunderkind. (Told you I learned German!)

It’s hard to run secretly, though. And people are going to look if you do burpees in the park.

Fitness — an area where I strive visibly for pretty modest success — was my first encounter with public failure.

Coding was a secret passion for well over two years before I began sharing it. And, even now, the teacher I respect most — my boss — doesn’t know that I have an amazing worksheet creation tool. If she doesn’t like it — or understand what it does — that would feel like failure to me.

I can’t fail

It’s a weird thing to say, especially in a reflection on a chapter titled “prepare for none of it to work,” but it’s true: I can’t fail.

The project might be a flop. It’s possible that it will always lose money and I’ll have to admit that the idea was only great for me. (Just yesterday, I heard a former and present student of mine talking about how much they loved the worksheets I make — so that seems unlikely).

And, I might spend years of my life with people asking “whatever happened to that website you talked about so much.”

The fact of the matter is, though, that I can’t fail. Already, I’m learning things like how AdWords works. As well as setting up a django site.

To that end, as long as I have a list of projects I’d like to apply that experience to, I can’t fail.

Something bigger than yourself

I’ve fallen behind in my weekly writings on the Obstacle is The Way, and I’m currently overwhelmed with work. But, I needed a break and decided to get the post about this chapter written as a treat to myself. I picked the chapter thinking I’d find it uplifting. I didn’t.


This chapter begins with stories that I’m supposed to find uplifting: the tales of U.S. Navy pilots who’d be shot down over Vietnam and were able to resist their captors in as much as they stuck together.

Unfortunately, the days of my looking up to John McCain are not likely to return because of a single anecdote in a single chapter, and so I mostly found myself thinking “Hmm, seems like moral fortitude is a resource that can get used up.”

And that’s not why I’m in this project.

However, later in the chapter, the musician Henry Rollins is quoted as saying this in the financial crisis:

People are getting a little desparate. People might not show their best elements to you. You must never lower yourself to becoming a person you don’t like. There is not better time to have a civic backbone. To have a moral and civic true north. This is a tremendous opportunity for you, a young person, to be heroic.

And I think I can get behind that. I can understand the idea that it’s worth remembering that, adversity is the only opportunity you have to really be heroic. Because anything you do that is easy for you is… well, easy.

Later, I got more into the idea when it was suggested that focusing on others could be a selfish coping strategy. (It’s the kind of thing I want to do, wrapped in the kind of thing I need.) The question is put like this:

If I can’t solve this for myself, how can I at least make this better for other people? Take it for granted, for a second, that there is nothing in it for us, nothing we can do for ourselves. How can we use this situation to benefit others?

[…]

You’ll be shocked by how much of the hopelessness lifts when we reach that conclusion. Because now we have something to do.

Of course the chapter continues, but it’s more of the same. That doesn’t matter, I like the idea of knowing that, when I feel helpless, it doesn’t mean there aren’t actions I can take.

Use Obstacles Against Themselves

I picked this chapter to write about because I was afraid that reading another chapter of “get to it, right now!” in my The Obstacle is The Way project would only serve to discourage me.


Gandhi didn’t firt for independence for India. The British Empire did all of the fighting–and, as it happens, all of the losing.

That’s how this chapter begins. And it covers, pretty well, what it’s about: the most direct, obvious action might not always be the best option.

And, to be honest, I appreciate this in the book, because there are clearly times in life when immediate action isn’t called for. Ryan Holiday goes on to mention more examples: He writes about Martin Luther King Jr. and the non-violent protests for civil rights. He even mention’s Alexander the Great breaking in his horse by simply waiting it out.

He even mentions the Mississipi river:

Before the invention of steam power, boat captains had an ingenious way of defeating the wickedly strong curent of the Mississippi River. A boat going upriver would pullalongside a boat about to go downriver, and after wrapping a rope around a tree or a rock, the boats would tie themselves to each other. The second boat would let go and let the river take it downstream, slingshotting the other vessel upstream.

The thing is this: there’s no real unifying theme behind all these obstacles, except that they all seemed insurmountable until they were surmounted.

That’s what, for me, this chapter is missing: some sort of tip that goes beyond “sometimes action isn’t the right action” towards explaining when it might not be the right action.

I don’t have an answer.

I do have a suggestion: perhaps rather than focusing on inaction, or using the obstacle against itself, another idea might be to say “what allies — including intangibles — can I find that might help me here?”

Ghandi was allied with moral right, and the fact that the British Empire’s behavior didn’t line up with its values. (Imagine a non-violent protest by Jews in the Warsaw ghetto and you’ll see that moral right alone doesn’t get you far.) Martin Luther King, Jr. saw that African Americans were in the same position and that the same strategies would work. The Mississipi boat captains were able to ally themselves with physics. And Alexander the Great was able to ally himself with patience, tenacity, and the limits to his horse’s endurance.

Even that, though, works applying it to the solutions found in the past. How does it help me with my problems?

At the moment, I’m frustrated by my inability to find users for my website. I’ll ponder it, but I don’t see how being unkown is the kind of thing that collapses in on itself.

But then, maybe this advice isn’t meant for me right now. Maybe I need to be doing more direct action.

Meditate on your mortality

It turns out that I accidentally wrote on a chapter out of order the last time I wrote in the The Obstacle Is The Way project. But, I liked it. So here’s another chapter chosen at random.

This chapter is a bit morbid, but my mind runs in these directions. It starts like this:

When a man knows he is to be hanged in a fortnight, it concentrates his mind wonderfully.

-Dr. Johnson

And that sets the tone for the whole chapter. It continues to the story of Michel de Montaigne, who nearly died in a horse riding accident and was left changed by his near-death experience.

Ryan Holiday describes it this way:

… Coming so close to death energized him, made him curious. No longer was death something to be afraid of–looking it in the eyes had been a relief, even inspiring.

Death doesn’t make life pointless, but rather purposeful. And, fortunately,  we don’t have to nearly die to tap into this energy.

The rest of the chapter can be summarized like this: we like to pretend we’re going to live forever, but we’re clearly not. So, let the fact that you have things you want to get done and limited time focus your mind.

Put another way: live each day as though you would soon die.

Normally, I get a little reflexively … frustrated by this line of thinking. I want to say “why should I save for retirement when I’m supposed to be living like the terminally ill?” “Who would have children in that circumstance?”

And it’s hard for me, even now, wanting to engage with the material, to not take that refuge.

But, the fact of the matter is, if I did die in a car accident tomorrow, I would be glad that I’d made time for my kids today. I’d hate for my last day with them to have been one in which I was “busy” with “work stuff” and left them feeling less important than they really were.

I did a good job today.

But, on the other hand, it’s a balancing act and the chapter doesn’t do enough to acknowledge that. On top of living each day as though I want my kids to have a great ‘last memory’ of me, I’m also trying to live each day so that we have the resources to do the same thing tomorrow and next year.

However, Ryan Holiday is right in saying that there isn’t time to complain about what isn’t fair, or how things should be (I tend to be guilty of this latter offense). If I’m already saying that the dual responsibilities of living correctly today and preparing to live correctly in the future are too much, then why would I take on the extra responsibility of letting everyone know that I’m unhappy with things?

And, as always, the chapter ends pretty well:

And so, if even our own mortality can have some benefit, how dare you say that you can’t derive value from each and every other kind of obstacle you encounter?

Anticipation (Thinking Negatively)

This chapter (in my continuing The Obstacle is the Way series) begins with an inscription from the oracle at Delphi:

Offer a guarantee and disaster threatens.

(Fun aside: I’d always heard that “Know yourself” was inscribed at Delphi. Realizing that there were other inscriptions lead me to this page.)

The core of this chapter is fairly straightforward: plan for things to wrong as much as you plan for things to go right, and you won’t be disappointed.

But, it’s a full chapter and it does include one reference to Seneca worth recording here.

…like all great ideas, it is actually nothing new. The credit goes to the Stoics. They even had a better name: premaditatio malorum (premeditation of evils).

A writer like Seneca would begin by reviewing or rehearsing his plans, say, to take a trip. And then he would go over, in his head (or in writing), the things that could go wrong or prevent it from happening: a storm could arise, the captian could fall ill, the ship could be attacked by pirates.

“Nothing happes to the wise man against his expectations,” he wrote to a friend. “… nor do all things turn out for him as hi wished but as he reckoned — and above all he recokend that something could block his plans.”

A good part of the chapter is reiterating that this premeditation of evils does not mean that the evils will be easy to bear, but that we are at least spared a shock and have the chance to prepare our ‘playbook’ before the emotional time of confronting a disaster.

I liked this chapter. It matches to me well, and to where I am. And, I like that there was reference to the process of thinking in writing (which is, basically, what this blog is).

So, maybe I’ll sit down and wrote a blog post as a premeditation of evils.

Do your job, do it right

Continuing my tradition of writing on each chapter in The Obstacle is the Way, and following my last post on this, continuing in my tradition of disagreeing slightly with Ryan Holiday.

This chapter begins with a story of Andrew Johnson being proud of his working-class origins, not as a link to the mythical ‘common man,’ but because he was a good tailor and continued to be proud of excelling even in humble work.

Then, it goes on to talk about James Garfield:

… paid his way through college in 1851 by persuading his school, the Western Reserve Eclectic Institute, to let him be the janitor in exchange for tuition. He did the job every day smiling and without a hint of shame. Each morning, he’d ring the university’s bell tower to start the classes–his day already having long begun–and stomp to class with cheer and eagerness.

Within just one year of starting at the school he was a professor–teaching a full course load in addition to his studies. By his twenty-sixth birthday he was the dean.

This is what happens when you do your job–whatever it is–and do it well.

I take objection to the last line. I could take objection because “hard work is its own reward” precludes doing hard work only because you expect returns of the sort that James Garfield got. But that’s not why. I think it’s ridiculous to hold up such a rags-to-riches story as an example of “what happens when you do your job” in 2018.

It’s not that I agree with the value of doing hard work. I believe that you are what you do, and if you consistently do sloppy work, you’ll be a sloppy person. The idea of “I can do it right when I have to” has proven itself wrong in my experience. (Naturally, I’m thinking of others when I say this, but I can think of at least one instance recently when I wasn’t able to perform like I should have on a job because I’d consistently slacked off with that company.)

In talking about this, Ryan Holiday eventually moves away from the idea of “you’ll get your just rewards in due time,” which sounds to me like something you’d say to someone who is being exploited, and gives better reasons for working hard:

The great psychologist Viktor Frankl, survivor of three concentration camps, found presumptuousness in the age-old question: “What is the meaning of life?” As though it is somene else’s responsibility to tell you. Instead, he said, the world is asking you that question. And it’s your job to answer with your actions.

In every situation, life is asking us a question, and our actions are the answer. Our job is simply to answer well.

I think that’s a better argument for doing the right thing, often, even when nobody is looking. However, I think that, if life is asking you “what is the meaning of life?” you’re welcome to answer: “not this.”

Follow the Process

This chapter of The Obstacle is the Way inspired me a little, but then I got a bit more… critical, I suppose. It starts off describing ‘the process’ in a sports metaphor. That’s not my thing, so I’ll use an example from later in the chapter.

After describing ‘the process’ as breaking tasks down into manageable chunks and focusing on them, the story of James Pollard Epsy is presented.

Unable to read and write until he was eighteen, Espy attended a rousing speech by the famous orator Henry Clay. After the talk, a spellbound Epsy tried to make his way toward Clay, but he couldn’t form the words to speak to his idol. One of his friends shouted out for him: “He wants to be like you, even though he can’t read.”

Clay grabbed one of his posters, which had the word CLAY written in big letters. He looked at Espy and said, “You see that, boy?” pointing to a letter. “That’s an A. Now youve only got twenty-five more letters to go.”

Espy had just been gifted the process. Within a year, he started college.

I don’t care how hard Espy worked, I can’t help but think that college admissions were easier back then.

Still, the idea is simple: if you know the steps to do, a project seems pretty basic. And, in his way Ryan Holiday mentions projects we can work on: a book, a novel, a new skill or an instrument. Each of them, he says, are about understanding the process and doing what needs to be done today.

And I get that. You won’t make progress if you only spend your time being overwhelmed.

However, if your process is simply to break a 50,000 word manuscript into 500 words per day, after a hundred days you’ll have your 50,000 words, but that’s not to say that you’ll have a novel. I think that the idea of ‘trusting the process’ only makes sense if you’re constantly re-evaluating the process (possibly that’s a process step that’s so self-explanatory that it needn’t be mentioned).

If, for example, you want to get good at making “things” online (as I do), how much should I focus on finishing up the one website I have working, and how much should I focus on the next thing? Either one of them presents enough work to fill all my free time.

I try to navigate this unknown territory by committing to having Dynamic-EFL.com finished, if only so that I know that I can finish things. But, the more I think “it’s almost finished,” the more I realize how much more could be added to it. So, I have one more review activity I want to add, and some polishing I want to do to the interface, and I’ll declare it done.

Then, I rationalize I can work on trying to attract users (something I’ve started doing) and get that extra experience and (hopefully) skillset while I work on the next thing.

Still, the idea of “a process” seems best suited to things like playing basketball or learning an instrument, where a lot of people have gone before you and signposted some best practices. When it comes to just getting the most out of my life, the “process” only tells me not to sit on my hands.

And, really, I knew to do that.

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.