Category: The Obstacle is the Way

Is it up to you

The seventh chapter in my The Obstacle is the Way project is titled “Is it up to you?” and opens with this quote from Epictetus:

In life our first job is this, to divide and distinguish things into two categories: external I cannot control, but the choices I make with regard to them I do control. Where will I find good and bad? In me, in my choices.

That is, basically, the entire chapter in a summary. The chapter talks a lot about Tommy John, a pitcher (I find it hard to relate to athletes) who played professional baseball longer than anyone.

The only bit that personally found inspiring was the part where he gets cut from the team and then asks his coaches if he would get a fair chance as a walk on at spring training the next year. They tell him they’d give him a look, and he trains up and (no surprise) makes the team.

Another bit of wisdom that I liked in the story was this:

He understood that as a professional athlete his job was to parse the difference between the unlikely and the impossible. Seeing that miniscule distinction was what made him who he was.

I hope that, someday, they’ll say “Toby was able to parse the difference between the unlikely and the impossible.”

The chapter talks a bit about the serenity prayer and how it’s easier to battle only alcohol than it is to battle alcohol and the fact that your childhood was miserable. I think there’s some truth in that.

Further, after a list of things that are outside of our control, Ryan Holiday includes a list of things that are in our control and I find it rather inspiring:

  • Our emotions
  • Our judgements
  • Our creativity
  • Our attitude
  • Our perspective
  • Our desires
  • Our decisions
  • Our determination

I like thinking that, in the mind of Ryan Holiday, at least, those things are under my control. It makes me think that I have a lot more tools in my toolbox.

Combine that with the overall lesson of the chapter: that there are far fewer situations that call for the use of those tools and it seems almost freeing to think that I have more tools than I thought I did, and need to fix fewer things that I had planned.

Even taking into account the additional time that will be required to wield “my desires” or “my attitude” as a tool, I should be freed up to do so much more of the stuff it takes to be me.


Alter your perspective

This is another post in my ongoing series on the individual chapters in “The Obstacle is the Way.” I don’t know how useful or interesting it will be out of context.

This is the first chapter in The Obstacle is the Way that didn’t really blow me away. The fundamental lesson seems like it can be summed up very briefly: how you look at things changes the way you react to them. And, either I haven’t properly internalized how profound that is, or it’s not Earth-shaking news following up on the previous chapters.

I get this. I was frustrated yesterday because I tried twice to make a sort of explainer video for the worksheet project. Both times, the webcame video didn’t record. (And I even put on a nice shirt for the occasion.)

I already said I was frustrated. I didn’t have time for a third run-through before work.

But, on the other hand, I had two great rehearsals. In the first, there were a few minor things that frustrated me. (I wanted it seamless, and there were a few vocabulary that didn’t have definitions in the system when I made it, to there were about two minutes of me entering vocab.) And the second one was smoother and much shorter.

When I get around to recording the same thing today, I expect it to be tighter, shorter. And that’s valuable.

I probably would not have, on my own, run through the whole video twice in preparation, but the whole webcam-not-recording thing upped the quality of the finished product.

That’s changing the perspective, according to the book. The obstacle itself cannot be changed. The idea seems to be that changing your perspective doesn’t necessarily change the amount of work you have to do, it changes your perception of the work, and that can be enough.

I’ll finish this with the two paragraphs that finish the chapter:

How we interpret the events in our lives, our perspective, is the framework for our forthcoming response–whether there will even be one or whether we’ll just lie there and take it.

Where thehead goes, the body follows. Perception precedes action. Right action follows the right perspective.

Practice Objectivity

This is another post in my ongoing series on the individual chapters in “The Obstacle is the Way.” I don’t know how useful or interesting it will be out of context.

In a chapter about how assigning values to things before we fully comprehend them, I think my favorite couple of lines are these:

Everything about our animalistic brains tries to compress the space between impression and perception. Think, perceive, act–with millisecond between them.

A deer’s brain tells it to run because things are bad. It runs. Sometimes, right into traffic.

I think I those lines for a number of reasons. I like the acknowledgment of our ‘animalistic brains,’ I like the visual aid, and I like the juxtaposition of the animal and the modern, because our animalistic brains weren’t made for the environment in which we live.

Which isn’t to say that they don’t offer anything of value, but that reacting to an upset boss the way you’d react to a predator–or even an upset ‘chieftain’ in a hunter-gatherer society–is counter-productive and one of the ways we repress ourselves.

I’m diverging away from the material of the chapter by getting into this territory, but something I’d like to examine better (or, read more about) is the fact that I don’t think people believe what they think they believe. When the animalistic brain reacts, the rational brain is a few steps behind and supplies reasons after the fact. (No, it would be tragic if my boss were to get angry at me, because…)

Getting back to the material of the chapter, the two paragraphs above are followed by the following two paragraphs:

We can question that impulese. We can disagree with it. We can override the switch, examine the threat before we act.

But this takes strength. It’s a muscle that must be developed. And muscles are developed by tension, by lifting and holding.

And, this is another thing that I think isn’t talked about enough: the importance of controlling yourself when it’s not super-important, because it will be much harder when it’s important. (For me, one example is being careful of how I speak to my kids when I don’t need to be careful about what I’m telling them, so that I have ‘muscle memory’ there for when I’m more concentrated on content than on how I say it.”)

The chapter only offers three strategies for doing this: contempt, describing things by means of their strict content, and thinking of your own problems as the problems a friend has. The rationale for this last one is that we’re more objective when thinking about our friends’ problems than when thinking about our own.

I think, if I could expand on this chapter, it would be to add priorities. Something that frustrates me is when a person complains about something in their life (the town where I live is so expensive!) but rejects all suggestions to make changes. Eventually, it usually comes down to something being more important (as long as my parents are alive, I want to live close to them). When a conversation reaches that point, I suggest “Instead of feeling sorry for yourself in such an expensive city, why not be glad that your parents are alive, and you’re happy to sacrifice having a big apartment for being close to them?”

It has been my experience that, if something is important to you, moving the ‘downsides’ of life in general into the appropriate ‘cost column’ in the accounting ledger of life makes a big difference. After all, we all think things along the lines of “there isn’t anything I wouldn’t do for goal.” That suggests, after all, that living in an expensive city is better than living in an expensive and dangerous city. You’re ahead of the game! The price could be much higher!

Control your Emotions

This is part of my continuing series on reflecting on The Obstacle is the Way, by Ryan Holiday.

This chapter begins with a quote from someone I’ve never heard of, Publius Syrus:

Would you have a great empire? Rule over yourself.

And, as you may have guessed, the rest of the chapter is dedicated to supporting that idea. The examples running through the chapter are primarily taken from NASA’s astronaut training and the idea that NASA had to–and was able to–train the panic right out of astronauts.

Obviously, we should learn to train the panic out of ourselves.

I think the paragraph that best exemplifies the thinking on panic presented in this chapter is this one:

Uncertainty and fear are relieved by authority. Training is authority. It’s a release valve. With enough exposure, you can adapt out those perfectly ordinary, even innnate, fears that are bred mostly from unfamiliarity. Fortunately, unfamiliarity is simple to fix (again, not easy), which makes it possible to increase our tolerance for stress and uncertainty.

So, because I think the sense of what he’s saying here is clear, let me begin with the obvious: I love the parenthetical “again, not easy.” Because there is a clear difference between simple and easy in this case.

I think that there are a few ways I can apply this to my own life. The last time I can remember panicking was probably during the fiasco of moving my software from the development system on my notebook to the Linux server I rented from Linode.

My emotions during the whole process were not helpful, and the thoughts they conjured up “the last months of work were pointless if I can’t get this software to work on a server” were destructive. I’ve since thought I should write a guide to putting your Django project on a Linode server — as much for me as anything else — and I realized that I no longer really know how I got it to work if I ever did know. I can recall several resets, and late evenings (with wine, which clearly didn’t help), where I would wind up changing things in configuration files “just to see what happened.”

Could I have managed that better? Certainly. Did I learn from it? I don’t know. Was the panic I felt in any way constructive? No. Should I have given in? Of course not.

I like that this chapter suggests that the exposure afforded my by having panicked once will help me face my panic next time. Now I know what it feels like, now I know how destructive it was.

But I’m not going to go looking for it.

The glorification of failure.

This all feeds into a minor rant that I could easily expand on. It’s this: from a distance, it seems as though silicon valley and, by association, startup culture in general really glorifies failure. I’ve heard things on podcasts like “nobody takes you seriously in the valley until you’ve had at least three failed startups,” and wondered “don’t they risk incentivizing failure?”

Incentives are a big thing in my life. I have three small kids, and I see the world around me in the terms of carrots and sticks. When parking fees are high, and tickets are cheap, isn’t the city incentivizing illegal parking? That kind of thing.

And I don’t like the idea that failure is incentivized. I think that trying should be incentivized, and failure accepted. There’s a clear difference (in my mind) and it wouldn’t have hurt whatever anonymous speaker made the “three failures” quote I mentioned above to have reworded: “Nobody takes you seriously in the valley until you’ve made at least three serious attempts at a startup.”

To me, there are worlds of difference.

Steady Nerves

In my continuing series on the individual chapters in “The Obstacle is the Way,” this is the third chapter, “Steady Nerves.”

The third chapter in The Obstacle is the Way is a short one, but it starts with a quote from Theodore Roosevelt, and who doesn’t love him?

What such a man needs is not courage but nerve control, cool headedness. This he can get only by practice.

The chapter is about the discipline of keeping your wits about you when it seems as though you should panic. It starts with some pretty impressive stories of General Grant keeping his cool even as things are exploding (or falling) around him.

Initially, I was a bit put-off by this chapter, because I’m going to get under cover if I’m fired upon, and certainly don’t intend to practice being unmoved by exploding artillery.

However, these are the two paragraphs that made it all much more approachable for me:

When we aim high, pressure and stress obligingly come along for the ride. Stuff is going to happen that catches us off guard, threatens or scares us. Surprises (unpleasant ones, mostly) are almot guaranteed. The risk of being overwhelmed is always there.

In these situations, talent is not the most sought-after characteristic. Grace and posie are, because these two attributes precede the opportunity to deploy any other skill.

I like that because I can see developing grace and poise as wise things to do, whether I’m strategizing how to be more effective or simply wondering how to grow as a human. And, there’s a wisdom in saying that, in addition to certain hard skills, you’ll need to be in control of yourself in order to develop them.

Like both the other chapters, it doesn’t take long for me to see where I can apply this lesson in my life:

  • Reading all the parenting books in the world won’t help  if I don’t have the self-control to apply what I’m learning in the heat of an exchange
  • Accepting that the worksheet app requires more administrative tools than actual worksheet-creating tools means I can buckle down to actually writing those tools
  • Learning to recognize when a ten-minute meditation would help me move my day forward is a good first step towards actually doing it

So, I guess I have something to think about in the coming week.

The Discipline of Perception

After reading the Obstacle is the Way, by Ryan Holiday, I recently resolved to re-read it more slowly, writing about what I read in order to reflect. This is part of that, and may only be of interest to me.


The first story in the Obstacle is the Way is of John D. Rockefeller, and the education he gave himself — basically — by remaining level-headed in times of panic. The lesson seems to be that there cna be a financial panic happening around you, but if you choose to see it as an education, that’s what it is.

My favorite line from the chapter is actually from Warren Buffet, who is credited with summing up Rockefeller’s mentality this way: “be fearful when others are greedy and be greedy when others are fearful.”

The actual lesson of the chapter seems best summed up here:

Outward appearances are deceptive. What’s within them, beneath them is what matters.

We can learn to perceive things differently, to cut through the illusions that others believe or fear. We can stop seeing the “problems” in front of us as problems. We can focus on what things really are.

This comes at a good time. In fact, I’m several weeks late in writing this. I’ve been working as hard as I can on the dynamic-efl worksheet app and consistently feel as though I’m almost there.

I’m so very almost there that I’m getting lazy. There is a (growing) list of minor things that I want to fix, once I get it so far that I can start asking others to take it for a test drive. But, it’s getting harder and harder to reach that point, because I didn’t do something I should have: I hard-coded everything to use the new domain name.

That means that it’s almost impossible to run in development mode on my notebook, and everything has to be tested out on the website. No big deal, really, except that everything is slowed down by committing every minor change to GIT, pushing it to Git Hub, and then pulling it to the Linode server and restarting the uwsgi service. Gah, it’s frustrating. (And that frustration is part of why the list of things I’m going to fix ‘later’ is growing.)

The reason I thought to read this now was that it was just this afternoon that I realized “I could be using this as an opportunity to practice overcoming problems, rather than feeling sorry for myself.” And that’s what this could be. Should be.

There are all kinds of lessons that I should focus on learning:

  • using django’s url tags to avoid hard-coding anything at all
  • setting up a project so that it can be easily changed over to ‘production settings’ with only a few changes in the settings
  • serving static files with django (turns out just copying a template from is not enough to make a landing page)

And that is what I’m going to try to do. There isn’t really a rush, as long as I can use it to make my own worksheets.

The trick is not seeing what it looks like, it’s seeing what it is.