Article from Succeed Socially
Many of the people who don't do well socially have poor self-esteem, and all the insecurities that come with it. Their feelings of inadequacy may even be the first problem they identify and seek help for. Before they start practicing things like their conversational skills they may have started looking at self-help websites for ways to feel better about themselves.
This article will discuss a handful of approaches for getting past low self-esteem. Obviously this is a complicated and wide-ranging problem. This one article can only suggest a few ideas, and can't totally solve the issue. Poor self-esteem comes in different flavors. Some people seem to have a negative self-image because they have real weaknesses. They may be down on themselves for being bad in social situations because they truly aren't successful in them. Aside from those problems their lives and upbringings may be fairly happy and average.
Other people may have a more deep-seated variety of poor self-regard. I admit that my knowledge about this area is much more shaky. They may feel worthless because of how their parents treated them when they were five, or from abuse they suffered at age twelve. They may still think they're fundamentally flawed no matter how much they achieve or improve. They may have everything going for them on the outside but still be totally insecure and down on themselves. In other words, their self-esteem is out of touch with how they're really doing. I can't say how much this article will help people in the second category. They may need other kinds of support.
Realize you can function even when you're feeling down on yourself
The strategies below may help in knocking away a lot of your self-esteem issues and insecurities... or maybe not. Either way there are always going to be times where you're feeling a bit down on yourself. You may always remain insecure about certain things. In these cases you can still choose to act as if you're not feeling that way, and still go after the things that are important to you. I'm not saying you have to act hyper confident, just that you can still carry out many actions regardless of how you're feeling internally.
For example, someone might eat lunch with their co-workers every day. Their mind might tell them things like, "Everyone thinks you're boring" or "Or they all talk behind your back about how short you are". They may not love having these thoughts, but socializing with their colleagues is something they value, and they can still do that even when they're doubting themselves, so they go through with it anyways.
Legitimately get over the weaknesses that feed your poor self-esteem
I think the biggest thing someone can do to improve their self-esteem in the long run is to chip away at their problems and accomplish the things that are important to them. This can do way more than a bunch of exercises where you list ten things that you like about yourself, but don't address the reason you're feeling insecure in the first place. For someone with interpersonal issues this may involve making friends, and generally becoming more socially competent. Sometimes you'll read that low self-esteem is caused by a discrepancy in how you compare your Actual Self to your Ideal Self. This point is about becoming more like the person you want to be.
This idea is not the whole story of course, it's just that I've read a lot of articles on how to improve self-esteem and hardly any of them mention the idea of actually improving in your weak areas. So I wanted to get that concept up there first because I think it's important and sometimes overlooked.
This approach does have it's limits though. Once you've reached your goals and smoothed over your biggest problems, you need to be able to move on to other areas of your life. In the process of overcoming their weaknesses, and feeling better about themselves as they do it, some people can veer off course and start base their self-worth too much on external accomplishments. They may think, "Well I started to feel better when I made new friends, so if I ever lose them it means I'm useless again." They may also develop this feeling that they have to keep attaining more and more in order to continue feeling good about themselves ("Well most people have a decent number of friends. I won't really think I'm worthy as a human until I have an absolute ton of them.")
As I mentioned, someone with deeper self-esteem issues may overcome their weaknesses and still feel bad about themselves. Getting over the weaknesses may have been part of the puzzle, but they'll have to address the more core issues as well.
Figure out a good plan to improve yourself
Getting over your real problems is best in the long run. A respectable bite may get taken out of your day-to-day insecure feelings as soon as you define your weaknesses and hit on a good road map for fixing them. Where before you may have more had these vague feelings of, "I suck. I'm a loser. No one likes me", your mind can now be more goal-oriented and think along the lines of, "Okay, I'm weak in areas x,y,z, and I need to do d,e,f to get to a better spot." Instead of seeing yourself as an unlikable dweeb, you can now view yourself as more a socially adept person in training. This can take the emotional element out of the equation somewhat; There's nothing wrong with you at your core, you just need to put in the time and the effort to get where you want to be.
Learn to cut down on your negative, harsh, and unrealistic thinking
Low self-esteem is all about how you think of yourself. If you work on your thoughts, you can make that thinking more positive. A lot of self-esteem advice falls into this area. These articles go into that thinking more:
Common Worries Shy Or Insecure People Have
Challenging Negative Thoughts
Cognitive Distortions
Seek reassurance from other people
This one should be used sparingly, and it only works in certain situations. Sometimes there will be some aspect of ourselves we're not sure about, but if we ask other people what they think, and they tell us everything is fine, it will make us feel better. For example, someone may not be sure how their new haircut looks. If their friends tell them they look good, they'll genuinely relax and stop worrying about it.
At other times someone may be so convinced that one of their insecure beliefs is true that no amount of reassurance will make them feel better. They may still feel compelled to ask their friends and family for reassurance over and over again, but it will never seem to work. In this case they may need to follow the point towards the beginning of the article, about acting in spite of what negative things their mind is telling them.
If you do think seeking reassurance from people will be useful, it's probably best to bring up your worry in a fairly casual, matter of fact way. Of course you don't want to go back to the same people day after day, with a new insecurity each time. This is more something to use every now and then.