12/20/2024

If you'd told me a year ago that I'd voluntarily spend 50 days in meditation retreats, I would've laughed. Meditation seemed like spiritual bypassing at best and self-sabotage at worst. I was sure it would dull my edge, make me passive, and rob me of the very drive that made me effective. Plus, I'd tried Headspace dozens of times and found it boring and useless.

What I wish I'd known #1: Meditation doesn't turn you into a peaceful zombie with no thoughts. It’s like plastic surgery: when it’s done well, other people might feel like something’s improved, but they won’t be able to put their finger on it.

Succumbing to the hype

For better and for worse, when you live in the Bay Area, there's no avoiding talking about it. So the idea kept reinserting itself into my consciousness. Bay Area Twitter is full of successful people making bold claims about meditation. They say things like: money is nice but hollow. Family brings meaning. But meditation? ”This is what you’re looking for, no doubt about it.” These people aren't monks or hippies - they're founders and engineers and researchers.

All this content primes you to reach for meditation when you’re feeling low (so I'm glad you're here reading this). What happened to me is that I tried my hand at founding a company and spent a lot of time mentally attacking myself for not being perfect. I didn't fully understand then why I was so often miserable, but fortunately I connected the dots and decided to give meditation another shake. So began 2024, my year of "emotional and spiritual fuck around and find out".

Despite being surrounded by supportive and inspiring friends, and having discovered real motivation, I still felt stymied. The meditation world can be frustratingly opaque about costs and benefits. I now understand where they're coming from. The purpose of meditation is awakening, but it’s like approaching a stranger at a bar: it doesn’t work if you're too needy. Learning too much about it before you start can therefore be counterproductive. But you still need enough information to make an informed decision about whether to invest your time.

What I wish I'd known #2: Yes, enlightenment is real, but most meditators avoid the word because it's got too much baggage. The highest stage is only possible for dedicated monks, but early stages of awakening are surprisingly accessible: most people can get life-changing results with less effort than a PhD. It’s easier in proportion to your baseline happiness, emotionality, relaxedness, and focus.

The gateway drug: pleasure states and their purpose

So I was so relieved to find Nadia Asparouhova's post about the jhanas, in which she clearly describes both benefits she felt (non-addictive yet intensely blissful absorption states called the jhanas) and the cost for her (about 20 hours of sitting). She is clearly an outlier, but at least I now had a lower bound. I also know and trust Nadia to be reasonable. And I was on sabbatical anyway. So I signed up for Jhourney and gave it a try.

What I wish I'd known #3: Not all meditation retreats are about sitting in silence for 14 hours a day and suffering through back pain until you spontaneously awaken.

The retreat itself was 8 days long. I had thought meditation retreats were about students sitting prostrate and receiving sacred teachings from some guru, which offends my unreligious tendencies. Jhourney, by contrast, establishes a frame in which you're an independent researcher of your own mind and the facilitators are like research managers that you meet for short interviews every other day. You're armed with all the content you might need on day 1 and then encouraged to go run your own experiments. The mood is akin to a search for buried treasure. And it only works if you’re feeling healthy and rested, so most folks were gentle on themselves as they explored.

This approach has a few outcomes that make it the ideal first meditation retreat:

It teaches you agency. Instead of receiving teachings too sacred for your feeble mind to comprehend, you realize that you're the only one that truly understands your experience, and that it's up to you to reflect like a scientist between sits and decide what to try next.
It gives you a clear signal that you're doing it correctly. Until your body feel awash in waves of bliss stronger than any emotions you've felt for 6+ months, and usually many years, you're not in a jhana. There's no mistaking it. I was astounded to feel the first two jhanas on my second day.
To do it correctly, you have to learn a lot of useful mental moves. The jhanas don't work unless you're sufficiently relaxed, which requires learning how to identify somatic tension and then doing the mental equivalent of unclenching your fist. You also have to learn to enjoy the process: think of the difference between an ox begrudgingly pulling a yoke and a husky enthusiastically pulling a sled. Poetically, they also don't work if you've suppressed too many emotions. As a result, many of the attendees spent their retreat learning to forgive themselves by crying in their rooms until their brains allowed them to let go into bliss. I think this is so, so poignant, and so funny. I just can't believe our brains work this way.

What I wish I'd known #4: For me, all of the meditation that I had done before my long retreats was useless. The whole game is about learning how to relate to your experience so that you suffer less. This view is subtle and unintuitive and you're unlikely to learn it without a great teacher and the extended focus that a retreat provides.

I'm lucky that I started my journey with Jhourney. Experiencing most of the jhanas was eye-opening and dramatically reduced my doubts about whether meditation is real and possible for me. But I also learned that collecting zany states is not the true goal. States are always fleeting. The real goal is to learn a view that reduces suffering, which requires investigating the nature of consciousness. But to get there, you first have to wrestle with your doubts. After Jhourney, my doubts had dropped by 50%, but I still had many potentially deal-breaking questions. Would equanimity make me a lazy slob? Can I really afford to add a daily sitting habit? Is happiness even what I was optimizing for in my life? I was already relatively happy most of the time, did I really need all this?

What I wish I'd known #5: Suffering is like being in a bad relationship. You don’t really know how bad it is until you’re out of it.

Beyond states: the core of meditation