The Discipline of Will

As I continue in the home stretch of my The Obstacle is the Way project, I thought a chapter on will was especially welcome today. As I’m trying to fit more into my days — more work, and more superpower activity — I’m learning to value willpower.


This is another one of the chapters that focus mostly on a single person as an example: Abraham Lincoln. And, it focuses on an aspect of his life that I hadn’t been aware of.

This is the opening chapter:

Because he has become more myth than man, most people are unaware that Abraham Lincoln battled crippling depression his entire life. Known at the time as melancholy, his depression was often debilitating and profound–nearly driving him to suicide on two separate occasions.

The thrust of the chapter following that is that Lincoln learned from his suffering — not just his depression, but poverty, and ballot box defeats — to develop a fortress of will that kept him safe.

Ryan Holiday makes the argument that we’ve come to believe that we can control anything, but that that is not true. That Lincoln excelled in learning what he could from experiences and allowing them to make him stronger and wiser and better prepared to confront the next hardship.

Of course, there is a reference to a stoic maxim, as well:

Lincoln was strong and decisive as a leader. But he also embodied the Stoic maxim: sustine et abstine. Bear and forbear. Acknowledge the pain but trod onward in your task.

And, there is a last bit of wisdom from this chapter that I will carry with me:

If Perception and Action were the disciplines of the mind and the body, then Will is the discipline of the heart and the soul. The will is the one thing we control completely, always.

When few other things seem to be in our control, it’s nice to know that there is one thing that is. When I’m busy with work assigned to me by other people and unable to do the things I’m passionate about, it’s nice to know that I still have the opportunity of training myself in the art of willpower.

It’s something that’s always available to me, and it’s something I’ll always be able to make use of.

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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.”