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.

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.

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.

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:

1. 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.
2. 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.
3. 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.

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?

Beyond states: the core of meditation

After Jhourney, something unexpected happened: I felt empowered to take on longer meditation retreats. I suddenly had a toolkit of techniques to explore and enough confidence to debug myself. This was fortunate timing, because I had already signed up for a 17 day silent and unguided retreat. And until I learned this toolkit, I felt deeply ambivalent about it.

I spent 10 days futzing around with the rest of the jhanas until I had satisfied my curiosity. Then I began investigating the nature of consciousness in earnest. By this point, I had a very strong base of concentration power built up, so it only took another few days to discover that my subjective sense of self was often intertwined with the thought patterns causing the mental tension that I was repeatedly releasing. These patterns manifested as an inner coach that had my best interests at heart but that was nonetheless clearly trying very hard to solve the problems caused by its own efforting. How endearing, I thought: the self is trying so hard to solve the problem of its own trying. It doesn’t realize that the solution is to just stop trying!

On a good retreat, you meet with a teacher every day or two to get feedback on your progress, and they got very excited about this insight. I learned that others had solved this problem by letting that inner coach simply burn out and give up, which seemed a long and painful process. I was begrudgingly open to that route, but I had an idea for a gentler experiment to try first: I’d congratulate the coach on a job well done, thank it profusely for getting me this far, and tell it that it wasn’t needed for the next step and that it could finally rest. This strategy worked pretty much immediately. Over the next half day, my inner coach became quiet, my entire mental landscape became utterly still, I realized a sense of giddy lightness in my heart was beginning to grow, and I entered another of those temporary zany states that dramatically reduced my doubts. Again, the states aren’t the point, or even a reliable preview of what enlightenment might feel like, but they are fun, so I’ll describe it here. I went for a walk and felt like I was floating across the pavement. My sensory clarity was unbelievably bright and lucid, like the resolution and saturation of my peripheral vision was turned up. There was no need for me to control my reality: I walked around campus feeling as though reality was unfolding all by itself, one time step at a time. And I was able to flip this blissful giddy feeling on and off like a light switch for three days.

Again, a state like this is not the point. But it drove home for me that this subjective sense of self is deeply intertwined with feelings of suffering so subtle, pervasive, and habitual that you don’t realize how heavy you feel until the burden is temporarily lifted. The goal is not to delete the sense of self. It will always still exist in a relative sense. But you do transition your subjective sense of self from a vague area behind your eyes to the field of awareness in general. This change in subjective origin is called “awakened awareness”, and talented students can glimpse it in a single week with the right teacher. For me, it took about 3. Stabilizing this view in all times and all situations doesn’t feel like always being in the giddy state. The first time you feel it, it’s like taking off a corset and breathing deeply for the first time. But after a while the state fades and your moment-to-moment sensory experience is largely the same. I’m told the long-term benefits of stabilizing awakened awareness are more subtle than that. I don’t fully understand them but I know enough to go for it.

For what it’s worth, my actual path was more winding than this: I did two 6 day retreats and two 1-day retreats before Jhourney, none of which had much impact. But I don’t regret any of my choices.

Early impacts

Even though I’ve only glimpsed temporary states so far and haven’t yet stabilized any view, these 50 days of retreat have already had noticeable impacts on me. I'm doing about 50% less mental rehearsal. I was never quite conscious of this, but I realize that I constantly prep for upcoming conversations or repeatedly run through mental checklists or remind myself what I’ll be doing next and how. I always felt busy, even when I didn’t have much responsibility. This divides my attention away from enjoying the present moment. This is what an optimizer's brain feels like: busy. This controlling orientation towards my reality has benefits, but is outweighed by the costs: it makes me more tired, tense, and inflexible.

The other change is more dramatic. I now intuitively respond to most of my thoughts and emotions with compassion instead of with analytical problem-solving. It’s so wholesome! During my most stressful periods as a founder, I would sometimes lie in bed in the morning for 30-60 minutes, ruminating, trying to think my way out of my problems and uncertainties. I've been amazed at how these anxieties simply dissolve in the face of self-compassion. It feels like a reduction in internal friction in my system. Have you ever felt dread around one stupid email, avoiding it for weeks, like there was a mental forcefield around it that made you resist thinking about it? Where I would previously try to enlist a friend to help, or just summon enormous willpower to overcome the forcefield, now I know to find the mental tension and give it heartfelt compassion, and it will just dissolve and I can see the problem clearly and just do the thing. This acceptance is what Buddhists mean by equanimity. As I heard once: "Nothing that comes up is a threat, it just needs your love."

This naturally extends into relationships, too. I'm noticing how often my "helpful suggestions" to others were really an instinct to leap into problem-solving action, where I would treat their anxiety exactly as I would my own anxiety. I have intellectually understood the value of emotional listening but until I started intuitively doing it to myself I didn't really feel the value. I had always regarded myself as someone who just preferred problem-solving. I strongly suspect that this path is transforming me from an unintentionally critical partner into a much kinder one.

The path ahead

So what's next? The current goal is to stabilize awakened awareness on the cushion, then gradually mix it into daily life, starting with easier situations. Once I feel confident that I can maintain this view while working, I'll return to my career. I think I can get to this milestone with another 2-8 weeks of retreat. After you practice mixing awareness with more and more parts of your life, it eventually becomes self-reinforcing. Once it's your default way of seeing, it just keeps deepening on its own.

I get why people are skeptical - I was too. None of my meditations amounted to anything before I discovered good retreats and was convinced to take them seriously. That's why I recommend starting with the jhanas: they're relatively accessible yet mind-blowing enough to convince you that all this baloney might work for you too. Save the longer and more gradual paths, like developing awakened awareness, for after you’ve developed more confidence in the path. Strong doubts are totally normal.

Looking back at all my initial skepticism - about becoming passive, losing my edge, or having to give up my normal life - I realize now how backwards those fears were. Meditation hasn't made me check out of life. I’ve been surprised to learn that it’s close to the opposite: I’ve already been partially checked out and I think these practices will help me live each moment more fully. Instead of making me passive, it's removed friction that made me indecisive. Where I feared it would reduce my agency, I now think it’s likelier to provide the opposite. The most agency-inducing question is “What would you do if you knew you could not fail?”, and in some real sense equanimity provides that by removing fear of outcomes.

Truthfully, I'd probably read versions of everything I've shared here before I began too. There's knowing something intellectually, and then there's knowing it in your bones. That's the thing I like about Buddhism: none of this requires any faith. At no point will a teacher tell you to just believe without evidence. It’s just a set of experiments that you can do. All of these experiences are baked into our consciousness already. Don't take my word for it. See for yourself.

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