I was shy when I was young (until mid way through college). My shyness was labeled as a problem. My family and friends said that I should enjoy going to basketball games and meeting new friends, going to parties, being social, etc.

As I grew up I realized that I really didn't enjoy what most people in the world enjoy. I don't enjoy going out to bars, clubs, big sports events, dancing, etc. I don't like attending parties and networking with new people. I really don't enjoy meeting random people while traveling. There are of course exceptions. But in general I've accepted the fact that it's OK to put myself in situations that I am most comfortable in.

I think a few things need to be clear to people that are shy now. First there is nothing wrong with not enjoying excessively social environments, there are (likely) other people out there who enjoy the same things you do. Second, it is OK to choose your friends and surround yourself with other people that stimulate and interest you. One really good insightful friend is worth 1000 contacts from all these social events that everyone thinks we should be attending. Third, ditch all the negative people around you because they will only add to any shyness. Lastly, you only live once. This has been a surprising motivator when deciding to attend or get involved in some social environments.

I think a blog like this is OK but it is also misleading. There are people who tend to be introverts, and that is OK. Our society does not encourage or allow introversion. It is considered "unhealthy" by the psychology and medical types. I argue that this is not always the case. A person can be introverted and private and do just about anything. For example: I know a circumstance where an introverted private person owns and runs a medium size (1000+ employee) company. I have seen him at social events where he attends (quietly) for whatever the least amount of time is to be polite and then he'll leave. I know another introverted private person who is a retired Vice President at a DOW 30 company (his division did $300+ million a year revenue). He is an excellent communicator with his core team and in small meetings or one on one. He, to this day, still struggles and is uncomfortable giving speeches or attending large events. It is absolutely possible to be successful and still be uncomfortable in large social situations.

Addressing a self esteem or self consciousness problem is important. It'll in fact make life easier and increase the likelihood of success. But it will not make you less shy or less introverted. It will make you better able to deal with those feelings. It'll allow you to put yourself in a situation that you wouldn't otherwise be in. But from my experience you will just be able to deal with being uncomfortable better than before.

Some additional background:

In college I decided I was missing out on something. That maybe there was something to all this socializing. So I went through similar steps to properly socialize myself and fend off my shyness. I began to attend house parties (even though I don't drink or smoke). I began to attend university clubs. I went to more spectator sporting events and extra curricular sports. Eventually I took on leadership rolls in a few different clubs. Later on I ran for senate at my university and was a senator for two years. By the time I finished college, my experiment complete, I decided that I would avoid uncomfortably large social situations whenever possible. There was no huge advantage to socializing on a large scale.

Now-a-days I'm a software developer. I lead a small group of people at a small company. Occasionally I have to lead meetings with 6-12 people in attendance. Rarely I'll get called on to participate at larger meetings. I'm still uncomfortable but I just do it.

On a personal note I socialize with a handful of close friends. I avoid most parties, clubs, bars, loud crazy restaurants, etc whenever possible. I prefer long in depth conversations with a few people. Done are the days where I'd meet 20 new people and talk to them about fluff. I go to dinner at places that provide some semblance of privacy and allow conversation. Occasionally I'll meet a new person and they end up being a close friend (which is great!). I no longer feel any societal pressure to attend uncomfortable social situations.

I think the best words of advice when it comes to shyness are "Just do it" and "You only live once".