I am a skeptical person by nature, and very few things trigger my skepticism as much as what could be uncharitably called "New Age bullshit." I used to put meditation squarely in that box, but that changed circa 2014, when I read Search Inside Yourself (and took part in a workshop based on the book offered at Google). The author of this awesome little book used to be a fellow software engineer at Google, and it seemed as if he had written it exactly with people like me in mind. Whenever, I would (mentally) exclaim yeah, right, my ass at his claims about something, he would promptly provide a citation to a study using fMRI or some other scientific technique I respected. So, I became a lot more open to the ideas. Unfortunately, meditation didn't have a stickiness factor for me. I would pay for an app like Headspace or Calm, and try to meditate for, say, 12 minutes a day. This should be enough to see some benefits, I would recognize them, but then life would get in the way and I after a few weeks I wouldn’t be meditating anymore. The reason for this was that even though intellectually I believed that meditation could be helpful, I didn't quite believe it really worked. I mean, yeah, sitting and relaxing obviously helped people who were stressed out, but I wasn't really buying the more out there claims of meditation enthusiasts.
One of the things that made me willing to try to give meditation another go was learning about the similarities between what happens in the brain of an experienced meditator and someone who took a psychedelic drug, like LSD. Sam Harris claims so in Waking Up, and if you are an aficionado you can read this paper co-authored by one of my favorite brain scientists, Robin Carhart-Harris. Learning this somehow warmed me towards both ideas. First, drugs like LSD are very tangible, they just attach to a receptor in your brain – nothing magical or spiritual about it. If Buddhist monks are able to push their brain into a state akin to the ones induced by drugs – there's definitely something more than relaxation coupled with powerful wishful thinking at work. Conversely, if psychedelics do something similar to what a Buddhist monk does after years of training, then maybe they are more respectable than just a substance giving you a particularly interesting high. (I am aware of, and slightly bothered by, the circularity of this argument.)
However, I still wasn't sure how to start in a way that would make it more sticky. This changed when my friend Amiran recommended to me The Mind Illuminated by John Yates (aka Culadasa). (Here's a review on Slate Start Codex.) This is a meditation book that reads almost like a technical manual. Do this and that, if you experience such and such problem, do this other thing. The author had a PhD in cognitive science, and it seems he was well aware of the stickiness problem. One of the first chapters is devoted not to explaining how to meditate, but how to kickstart your meditation habit (which used to be my problem). What is very encouraging is that since I started following the book, I am experiencing the thing it says I would experience, in roughly the order it describes. The book is also mercifully light on Sanskrit or Pali terminology, and makes extremely few ontological claims – it has very few ambitions of changing your worldview directly. All this changed my perception of meditation from some sort of magic to a skill that an engaged regular person can learn. What is more, as I became more serious about it the process turned out to be surprisingly not boring. I started studying the book at the beginning of the summer – ask me how it goes a year from now. (When I read a book I really, really like I usually want to learn more about the author. This was a bit of a downer in this case. Shortly before his death at 76, Culadasa did what seems to be a quintessential Buddhist master in the West thing and became embroiled in a sex scandal. Not as scary as some other sex scandals – apparently he had been cheating on his wife with numerous prostitutes for many years – but still too much for his Buddhist community. Again, Scott Alexander has an interesting blogpost about it. I think this book is so good it’s worth keeping the work separate from the author’s personal life in this case.)
Finally, when you get more enthusiastic about some topic you may feel that it helps you stay intellectually honest and not become... overly enthusiastic. The book that fits this bill is Altered Traits by Daniel Goleman and Richard Davidson. The former is a science journalist for the New York Times, who also wrote the book about Emotional Intelligence. The latter is an esteemed professor of psychology, and one of the OGs when it comes to meditation research. The book, as plenty others, explores what cognitive science is starting to know about meditation. However, two things make it stand out. First, the tone is a lot more personable than what you would expect, which makes it a pleasure to read. The authors describe their own trips to Asia to learn to meditate as young people, and there's plenty of complaining about unsympathetic older colleagues (back when behaviorism was psychology's de jour ideology). Second, it has a firm focus on methodology. The author dig deeper into the shortcomings of various studies, including their own work. So, you get to see how the science sausage is made (and how Davidson needed to throw away some of his early research results because he used the wrong kind of EEG paste), and you get the tools to assess for yourself how methodologically sound are various papers about meditation that are being published these days (tl;dr: many researchers tend to have weak controls or to have very little understanding of various meditation techniques and conflating them together).
For me, meditation stabilized in my routine once I managed to stop striving to “achieve” X, and find a frame where it’s a place of rest, nourishment, and meeting myself as I am in that moment. I’m a bit sceptical of the pragmatic dharma folks, because it often comes with a whiff of achievement, of striving. But that’s mostly my own hang ups - I haven’t given culadasa, Ingram, or the others a fair chance, and it’s possible I should.
The guy I’m currently most excited by, in a similar vein, is Rob Burbea - might be worth having a look at some of his talks or books. Quite a different twist on things, but very philosophically stimulating!