“With insomnia, nothing’s real. Everything is far away. Everything is a copy, of a copy, of a copy…When you have insomnia, you’re never really asleep and you’re never really awake.”


Fight Club


Given that I’ve spent most of the last ten nights struggling to sleep, I’ve had ample time to ponder how sleep can be seen as a metaphor. It’s actually the perfect metaphor for ‘waking up’ (enlightenment), which is ironic given the effects, goals, and methods of falling asleep and awakening are so radically different.

There I was, hour after hour, tossing and turning in the bed, waiting for sleep to come. It didn’t matter how fervent or earnest my desire was; it was pretty clear, in fact, that the harder I tried to fall asleep, the further I pushed it away.

So it was for many years with enlightenment. As I describe in my book, I dedicated myself wholeheartedly to ‘getting’ enlightened… and all I got in return was self-doubt, fear, and misery.

Just as I tried every position and remedy to fall asleep, I sampled all the various techniques and elixirs that I hoped would awaken me. I longed for enlightenment as an insomniac yearns to be released from his tortured state.



I should have known better, I suppose, than to think that bringing about sleep or enlightenment was merely a question of will. I should have been tipped off by the fact that we don’t use rise, climb, or any other verb that has an active connotation to describe sleep. No, we use the verb  fall asleep, because sleep is something that happens to us, not something we do.

For the process of sleep to overtake the body, or the realization of enlightenment to blossom, all ego-based effort must be set aside.  The ‘I’ who is trying so hard to attain something has to move out of the way for nature to take its course.

But there’s a paradox about this: we have to make much effort to arrive at the place where we make no effort!

With sleep, you have to switch off the lights and get in a comfy bed. And to arrive at a place where we embody effortless effort, where enlightened actions flow spontaneously, it’s helpful to set aside meditation periods and practice steadfast ethical discipline, generosity, and other virtues.

So it seems that waking up and falling asleep are both active and passive (or neither active nor passive).





My sleep issue was resolved a few days ago when I went to blind Thai massage master. For 10 minutes, he gave me the most excruciating shin massage, saying my sleeping problems were caused by “too much air in the muscles.” I have no idea whether that was literally true or not, but whatever he did, it seems to have worked (knock on wood).

[Aside: the whole atmosphere in that place was hilarious.The entire time the three blind masseurs/euses casually chatted while they put crazy pressure on our bodies. At one point, a fairly plump woman came in and started counting a huge bag of coins in front of me. Then her daughter arrived and the first thing she did was breathe in front of her mom’s face (to prove no smoking or drinking, perhaps?). The best part was the Thai guy next to me who was texting the whole time during his massage, then at one point just fell asleep (god knows how!).]

I can’t say that I’ve really resolved the enlightenment issue, however, since to make such a claim would mean that I’ve understood what enlightenment is. But to arrive at a place of peace, where I don’t feel absolutely tortured all the time, I also had to have the ego-air of trying so hard “taken out of me.” I had to cultivate the humility to ask for help and admit that I didn’t know any better.

When we have sleeping or spiritual troubles, there’s a lot of vulnerability and tenderness that arises. It’s tough to remember that this isn’t a bad thing, and that it can actually be quite powerful and instructive to let ourselves truly feel lost, desperate, and confused.

Even when we do all the ‘right’ things to facilitate sleep (reduce coffee, increase yoga) there’s no guarantee that we will have the results we seek. This is one crucial aspect of my biological wellbeing that is largely out of my control.

This is a microcosm for life as a whole. Who knows if I will get cancer, or get hit by a bus, despite doing all the ‘right’ things? Like most people, I operate under the illusion that I am the choreographer of my life, when the reality is that I am subject to countless forces and conditions outside of my personal control.

Perhaps the path of enlightenment is to familiarize and make friends with this uncertainty that is at our core, that never really goes away no matter how much we distract ourselves.