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.

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Iterate

I enjoyed this chapter of The Obstacle is the Way more than the last one. It didn’t seem to be as cliché, and it talked about iterating, which is something I’d already believed in.

The first concept introduced is the idea of the “Minimum Viable Product.” It’s something you’ll hear about if you follow startups much, the idea that you make the smallest possible version of your product and see what people say. (Rather than, as I seem to have done, making a full-featured product and then releasing it to the world.)

The idea is that, people will tell you what’s great, what needs to change, and your product can grow into greatness, rather than you needing to brainstorm that greatness locked away in solitude.

Or, on the other hand, if nobody likes what you’ve made, you move on to the next thing having lost as little as possible.

I like the idea.

Ryan Holiday goes on to say this:

In a world where we increasingly work for ourselves, are responsible for ourselves, it makes sense to view ourselves like a start-up — a start-up of one.

And that means changing our relationship with failure.

Maybe it’s because I enlisted back when “an Army of one” was a thing, but I loved that. And, I loved that he went on to say:

Our capacity to try, try, try is inextricably linked to our ability to fail, fail, fail.

It’s true.

The chapter is a good one, but that’s the core of it right there. (The only historical anecdotes are back to Rommel in the desert again.) but there is one more thing I wanted to quote, beginning with a question that the reader is hypothetically asking him or herself:

Well, why would I want to fail? It hurts.

I would never claim it doesn’t. But can we acknowledge that anticipated, temporary failure certainly hurts less than catastrophic, permanent failurE? Like an good school, learning from failure isn’t free. the tuition is paid in discomfort or loss and having to start over.

I think that’s all true and, on that note, I’m off to start paying my tuition.

(As an aside, the Work Life Podcast has a great episode about embracing negative feedback, but I can’t see how to link to individual episodes.)