I learned that failure is by and large due to not accepting and successfully dealing with the realities of life, and that achieving success is simply a matter of accepting and successfully dealing with all my realities. — Ray Dalio, Principles

When I was a kid, I was stuck in a very silly cycle.

I’d get home from school every day and I’d avoid doing my homework for as long as possible. Why? I didn’t like homework, I guess. It seemed boring, tedious, unimportant. And I assumed I’d be able to do it really quick whenever I finally decided to do it.

I’d tell myself that I’d get it done before going to bed, and go on to watch anime, play video games, read books, etc. I spent all my time in the Dark Playground. Next thing I’d know it would be 1am, and I’d be really tired and sleepy with nothing done. I’d sit with my books for maybe 30 minutes to an hour, sometimes with a can of coffee or Red Bull. And I’d have the sinking feeling that I was somehow ‘mysteriously’ in a terrible, no-win situation.

Eventually (maybe around 2am), I’d get exhausted and try to bargain with myself. “I can’t work like this. Let’s sleep for a couple of hours, set an alarm for 4am, and get it done before school starts.” I’d almost always sleep through the alarm, or wake up groggy and decide that sleep is more important. Finally my mum would come into my room and wake me up to go for school. At this point I’d be panicking and anxious. I’d try to get my work done on the bus on the way to school, or I’d try to sneak off and do it somewhere. If I knew that the teacher was going to be especially mad at me, sometimes I’d convince myself I was sick. Sometimes I’d actually fall sick, and I’d feel sorry for myself for having to suffer so much.

The funny thing is, I never really questioned the assumption stated earlier.

I simply assumed that I’d be able to do my homework really quickly when I decided to. I systematically, consistently, repeatedly miscalculated how much time I would require to do the work. I never bothered to measure how much time it took me, and I’d get burnt over and over and over. And when I’d fail, it would never occur to me that my assumption might be wrong. It was like an optical illusion, a persistent bug in my mental software.

Why? It seems to me that it’s because it was easier and more comforting to maintain the illusion than to confront reality.

This weird habit has stuck with me my entire life so far. To this day I continue to overestimate how much I can do in a given time period, even when it’s now work that I recognize as important to me. I constantly assume that I’m somehow special, and that this time is different. The cycle of denial and bargaining is troublingly similar to the sort of patterns we see in alcoholics and drug addicts.

What exactly is going on here?

The Ray Dalio quote says it all: I was refusing to accept and deal with reality. (This is still a problem.)

Specifically, the reality of my own personal capacity and ability. It was somehow comforting or self-assuring to believe that I possessed some sort of superhuman capability, that one day I would wake up and be overcome with inspiration and completely decimate my todo list and take care of all my obligations all at once. (Hyperbole and a Half covers this quite well.)

The longer I live, and the more experience I accumulate, the more painfully obvious that this isn’t the case and will never be the case. I make fun of people who play the lottery, and yet inside my head I’m playing some kind of lottery too. I keep betting on vanishingly tiny odds that I’ll be able to do something I’ve never actually done before, and I keep getting burnt for it. I suffer from a sort of Gambler’s Fallacy– this dogged belief that somehow I am special, somehow I’m going to beat the odds, my day will come, yadda yadda.

So that’s the first trap. Believing in something that isn’t true, partially because it’s comforting, because it’s easy, and because it enables me to feed my addiction(s). It’s a lie that that the wily saboteur in my head tells myself.

Then there’s a second trap. After several failures in a row, and being confronted by the nasty outcomes of said failures– angry teachers, angry parents, stress, frustration, shame, etc– I often have a “moment of awareness”. A moment where I temporarily open my eyes and go “Wow, this is messed up.”

The correct thing to do would be to go, “I should do something to fix this,” and then execute the fix. But that’s hard, and boring, and painful.

The simpler, easier thing to do is to get fixated on my feelings. I feel bad. I feel guilty. I feel ashamed. I feel embarrassed. I resent myself. I beat myself up internally as some sort of penance for my sins. THIS IS A TRAP. It feels like there’s some sort of important emotional labor going on, but it actually achieves nothing. In fact, it actually distracts from the actions needed to be taken in order to rectify the problem.

Imagine an alcoholic crying and pleading with her loved ones, saying “I messed up, I’m so terrible, I’m so sorry,” and then getting drunk again afterwards because she feels so bad. That’s basically what happens.

Consider how, in the broader scheme of things, the intensity and seeming sincerity of the self-flagellation is actually far less relevant than the subsequent actions that the person takes. And yet somehow there’s often this strange impulse to focus on how big and important the feelings are.

Beating yourself up over your failures is every bit as egotistic as convincing yourself you’re amazing. This seems like an unpleasant thing to say, but I’ve found it to be true. And that’s not a coincidence– the more unpleasant the truth, the less likely anybody’s going to intervene, and now you’re trapped in this delightful ego bubble of Poor Little Me.

Let’s talk for a second about how people react to seeing a person like this. There are a few responses:

1. Comfort them (“It’s okay, you’re okay…”)
2. Confront them (“What is wrong with you?”)
3. Ignore them (This depends on the relationship between the two people– easy if it’s an acquaintance, harder if you live or work together. Sometimes people slowly disengage and distance themselves over time.)

The ego likes all of these responses. When comforted, it feels good, and nothing gets done about the problem. When confronted, it gets defensive, and now we’re fighting about other things instead of addressing the problem. When ignored, it continues to fester in its filth.

The only real solution I’ve seen is a sort of enlightened, questioning engagement. (My boss is really good at this. He has a way of simply asking questions in a non-accusatory tone, which my ego has no idea how to deal with. He’d ask, “How come this didn’t get done when you said you’d do it?”, and my brain would think, “Because I’m a horrible person!” — which is the ego talking, again. But he’d ask it in such a neutral, curious tone that he’d get me curious too, and make me realize that I personally avoid identifying the real causes. Because the real causes are boring to behold and painful to deal with– it boils down to things like sleep, nutrition, keeping a schedule and sticking to it, all the little things that require effort that don’t immediately yield nice payoffs.)

The ego, or the saboteur, whatever you want to call it– is only interested in narrow, unenlightened self-preservation. It wants to maintain the status quo, and it will cry and whine and rage and scream to do it. There’s a parent/child dynamic at play here, whether internally inside the person’s head, or between the person and others. And the goal of the child is to get away from the “problem” or “pain” of being held accountable. It will do whatever it takes.

If you’ve ever witnessed children manipulating their parents in order to get ice-cream or fast food, you’ll know how horrifying it can be. It sometimes literally looks like the child is possessed by some sort of demon. Then think about how there’s a demon inside you too– it cooperates when you do what it wants, but otherwise it raises hell.

There’s a third trap beyond the first two layers. The one where you think you’ve finally got it. Where you recognize the first two traps, and you’re convinced that you’ve got it figured out, that it’s not going to get you anymore, so you don’t need to “police yourself”. [1] And so you happily, confidently write a blogpost about it and share it with the world, problem solved!

Nope, that’s another trap. Everything about the ego resists examination, introspection, accountability. This is such a reliable, predictable thing that you can practically navigate by it: Whenever you start to feel like you’ve “solved the problem”, realize that you’re being hoodwinked. Instead, develop a taste and appreciation for doing the work.

I’ve actually written many variants of this blogpost many times over the years. “I didn’t do well because I didn’t study” [2013], “Killing the Saboteur” [2014], “Searching under streetlights” [2015]. Evidently, my ego really enjoys doing this sort of thing. Time spent writing about a problem and outlining a problem is time spent not addressing the problem. Commiserating feels good, but it ends up feeding the ego too.

The only way out is to confront and accept reality. To navigate not by feelings (which are misleading and manipulative if you have a saboteur in your head like I do), but by evidence. For me, this means taking a good hard look at my calendar every day, keeping track of the work I’m doing, seeing what my output actually is, how much I can actually do. It means developing a taste for pain and discomfort. It means revisiting and reviewing how each day goes, so that I can make adjustments and learn from my mistakes and do better.

And it means ending this essay here, and getting my ass to work. 😛 I hope this is helpful to somebody.

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[1] I’m not saying that you DO need to police yourself. That’s very loaded language, and it’s designed to fail the same way unsustainable diets are designed to fail. You need to discipline yourself, the way a musician or comedian is disciplined– they improvise on stage, but they put in decades of deliberate practice beforehand.

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