Bryan-san comments on Open Thread, Jun. 22 - Jun. 28, 2015 - Less Wrong
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Does anyone know about any programs for improving confidence in social situations and social skills that involve lots of practice (in real world situations or in something scripted/roleplayed)? Reading through books on social skills (ie. How to Win Friends and Influence People) seems to provide a lot of tips that would be useful to implement in real life, but they don't seem to stick without actually practicing them. The traditional advice to find a situation in your own life that you would already be involved in hasn't worked well for me because it is missing features that would be good for learning (sporadic, not repeatable, can't get feedback from someone who knows what they are doing on your performance, have a lot of things going on beyond the aspects you want to focus on, things can move on without giving you time to think, etc.). For example, this might look like a workshop that involved a significant amount of time pairing up with other participants and practicing small talk, with breaks in between to cool down, get feedback, and learn new tips to practice in later rounds.
The Rejection Game using Beeminder can be a good start for social skills development in general
If you're interested in a specific area of social interactions then finding a partner or two in that area could help out. Toastmasters, pua groups, book clubs, and improv groups fall into this category.
Alternatively, obtaining a job in sales can take you far
My impression of Toastmasters is that it might be similar to what I'm looking for, but only covers public speaking.