I can hardly believe it, but I'm actually thinking (rather impulsively) of getting a ticket and buying plane flights to the LessOnline conference in San Francisco that will be at the end of this month. My primary motivation is the one you'd expect: I want the experience of prolonged meatspace hanging-out and discussions with serious rationalist people. I could get this at the NYC Rationalist Megameetup, which is whole lot closer to where I live, and I have attended the Secular Solstice part of it these last three years, but I don't know if I'll ever make it to the full Megameetup since December is a very stressful month for me as an academic; late May / early June, on the other hand, is a very easy time for me to take a break from work. (I wouldn't even have to tell my colleagues that I'm leaving for a weekend, let alone what I'd be doing, which I'd prefer to keep separate from my professional life as long as that's in academia.) And the NYC rationalist crowd is obviously a different one from the (much more central) rationalist crowd I'll find in the Bay Area.
The other motivation, though, is that I'm at a critical point now where I seriously want to consider a career switch to coding, but I'm extremely agnostic on whether this is a good idea, especially with the state of AI, and I have a feeling there might be a coder or two at this conference that also just might have an opinion on the future of AI.
It also looks like the total cost of travel, lodging, and ticket, and main meals would come to $1000 or not much more (more than half of which would be the ticket!), which is something I can afford and doesn't feel too frivolous, especially given that I now pretty much know I'll still be gainfully employed after this summer.
One suggested activity mentioned on the LessOnline website is writing a small essay with a provocative thesis and being prepared to read the essay out loud and discuss/debate it with a small crowd. I'd be quite interested in doing this and even have an idea about what thesis I would defend (it's one I've never declared or defended head-on here, in fact).
Pros of going: I have an extremely blank and free summer ahead of me that needs enhancing with a little traveling and small diversion or two rather than just sitting with my head down trying to work on research; it sounds incredibly fun in every detail; I'd finally get to meet people I've admired from afar for years like Scott Alexander and Aella; maybe I could meet a few people I know from Tumblr as well; I'd learn something about the Bay Area programming world (which I'm entertaining thoughts of joining, if it can be in a way that doesn't involve physically moving there); I'd be inspired by and get to learn more about rationalist culture; there would be almost zero stress involved in terms of missing other responsibilities; not too many people would even have to know what I'm up to.
Cons of going: it'll still take me away from work for a long weekend; it's still an unexpected expense; travel (especially plane travel, especially across a long distance) tends to stress me out; my risk of blending my online-under-Liskantope life with the rest of my life would be increased; just as at the (much briefer) Secular Solstices, I would become depressingly aware of how not-a-true-committed-rationalist and how poor an effective altruist I am, not even having ever made a GiveWell pledge or been active on LessWrong; I would feel dumber than most of the people there and would have trouble following, let alone contributing, to many of the conversations; the sensation of being an imposter (outside of the possible essay-discussing activity mentioned above) would probably be severe. (The first three or four of these cons feel fairly minor, while the last ones give me pretty serious reservations.)