Overall Attitudes That Will Help You Improve Your People Skills
You could also call these "meta-attitudes". They don't directly have to do with being better with other people, but having them will help the learning process go more smoothly. Like all attitudes, attaining them is easier said than done, and not just a logical matter of deciding they're good beliefs to have. You have to slowly cultivate them.
You have a long-term, bigger picture perspective
This means recognizing that you're on a journey to some far off destination, and that getting to the end is much more important than all the little hiccups that happen along the way. The first reason having this perspective is helpful is that if you're fairly awkward and unconfident, then improving your social skills is a longer-term project. I go more into this point here:
Secondly, if your perspective is focused on the bigger picture, you'll be able to handle the day-to-day frustrations of working on yourself more easily. Whatever your long-term goals are, you're going to be repeatedly practicing various skills as you work toward them. You're going to make mistakes. It's a part of learning anything.
If your perspective is rooted in the short term then you'll get freaked out by every small thing that doesn't go your way. You'll let a bad week, or a single stilted conversation discourage you. From a broader perspective none of these little ups and downs matter. All that's important is that you're making steady upward progress over a longer period. If you're trying to get over your shyness, and the last month hasn't been too productive, what's it matter if a year from now you'll still be way more outgoing?
You're not too hard on yourself
Again, easier said than done, but the process of improving will be a lot less painful if you don't beat yourself up too often, or have unrealistic expectations about how you should be doing. Being a little shy or awkward is something billions of other people have gone through. It's not some curse that only you have ever been afflicted with. Some of this is covered in the previous section about not getting too caught up in short-term details. Another point is:
You realize you don't need to be flawless to have social success
It's pretty common for people to be too tough on themselves, think they have to be socially perfect at all times, and see little mistakes they make as the ultimate proof that they're unbearably awkward. Of course, that's not realistic.
No one has a defect-free personality or makes the right social choices every time. We all have flaws that sometimes annoy other people. We don't always come off the way we'd like. Sometimes our conversations are forced and go nowhere. Sometimes we make corny jokes that get a pity laugh at best. You're not perfect, but neither is anyone else, and by-and-large most people still get by.
Another thing, one that you've probably heard before, is that everyone has their insecurities. Good looking, seemingly together, confident people get nervous too. They worry about how they come across to their friends. They may also get insecure about little things that you have no problem with (e.g., feeling anxious when they first enter a party and everyone turns to look at them).
Finally, you can't win with everyone. Some people just aren't going to be drawn to what you have to offer. There are criticisms of Ghandi and Mother Theresa. As long as you can get enough people to like you that you can have a solid group of friends, that should be enough.
You try to see yourself accurately
It's hard to improve yourself if you have a blind spot to half your problems. Self-awareness takes a long time to develop. Putting your ego aside is important as well. If you're too invested in seeing yourself as perfect and flawless, your mind will keep you from seeings the spots where you can make improvements. We've all known someone with a ton of issues, who thought they were awesome, and that all the problems in their life were the fault of other people or outside forces. Of course, they were in no position to make any real changes.
While cultivating self-awareness is useful, so is finding ways to get objective outside feedback:
You have a healthy level of self-centeredness
By this I mean on your path of self-improvement you strike a good balance between focusing on your own development and considering other people's feelings. You don't become completely selfish and self-absorbed, but you also don't over-prioritize everyone else's needs and neglect your own. For example, you're at a bar and want to practice starting conversations with strangers. Not everyone may be open to chatting to you. Some may even find it bothersome to be approached by someone they don't know. However, you're allowed to speak to people in a pub. As long as you're polite and respectful and don't stick around when it's clear you're not wanted, you're not doing anything wrong. It's okay to value your social development, and risk bugging people in a minor, fleeting way in order to reach your goals. It would be self-sabotaging to never put yourself out there because someone might get a tad annoyed.
You're open to learning how you could do better in your interactions, while also accepting you can't control everything
After talking to someone it can be useful to take a few minutes to objectively think about how the interaction went, and if you can learn something from it. That's especially true if the conversation didn't go as smoothly as you'd like.
What did you do well? Did you make any mistakes? Did you go in with a counter-productive mindset? And so on. The idea isn't to mercilessly tear apart your performance, but to see if there are any corrections you can make going forward. You don't need to dissect every conversation for the rest of your life. But a little over-analysis is fine if you're in a period where you're really working to get past your awkwardness.
However, while it's good to consider how you could do better next time, you also want to remember that it takes two or more people to socialize. If a conversation goes badly it's not always your fault. Sometimes you can do everything right and still have the other person be closed-off or rude because they were just in a cranky mood that day.
You don't look at changes in a Black and White, Either/Or way
Viewing the world in extremes is a very common cognitive distortion. Some people have trouble improving themselves because they think of possible changes as being All or Nothing. They either remain totally true to themselves, or they completely sell out. They either never learn to make light small talk, or they become a vapid idiot who can only gossip about celebrities. They never teach themselves to mingle at parties, or they become a mindless drunk who kicks over mailboxes every weekend. They can't see themselves going to the other end of the spectrum, so they do nothing at all.
Most changes can be made in degrees. You can choose a middle ground that fits your goals. You can mostly remain true to yourself, but make a handful of pragmatic changes. You can make small talk when the situation calls for it, but still have deeper conversations whenever you can. You can get better at socializing at parties, but while choosing not to drink or be rowdy.
You have confidence in your ability to figure things out for yourself
When I look back over my own social improvements I don't think this was the biggest factor in getting past my problems, but it's one that stands out in my mind. I consulted tons of other sources for advice, but overall I felt that I was the one charting the course of my own development. I took and used piles of outside information when I needed it, but it all came back to me calling the shots.
If I didn't agree with some advice, and felt I had a good reason to disregard it, then I did, even if it had a good reputation. If I couldn't find a solution to a certain issue in outside sources, I cobbled one together on my own. Another big reason you need the ability to figure things out on your own is that no advice is going to cover every situation you'll personally encounter. So you have to be able to use your own intelligence to fill in the gaps. You won't always get it right, but you won't always get it wrong either. With time and experience your instincts will improve.
So what goes into this? The ability to critically evaluate what you read for one. A non-passive attitude is also important. Don't just wait for someone to tell you what to do, unconsciously assuming that any of your own ideas aren't worth considering.
Another important thing is not being too prone to hero worship. Or put another way, you don't put some person/author/speaker up on a pedestal, while simultaneously discounting your own views, or not bothering to form your own opinions at all. Yeah, you might respect a writer's work, and they may be more knowledgeable and experienced than you about an area you're interested in, but at the same time, you're closer to them than you think. They're people too. Their ideas aren't spotless. You know more than you give yourself credit for. You may even know more than some of the people you're taking advice from. They could just be hack marketers who anointed themselves as experts to sell you something.
All this isn't to say that you should become self-deceptive, hyper-critical, and arrogant and write off everything you don't agree with. A lot of the time you do need to turn to someone else's suggestions. I'm more saying to have confidence in your own ability to pull yourself out of your hole and to not feel it's only going to be other people's teachings that can do it for you.
You're able to carry over positive mentalities from other areas where you've been successful
People who are shy or awkward are often accomplished in other areas, but often have trouble carrying the attitudes that all helped them in those fields over to socializing. For example, a guy who would be persistent and power through a tough science concept, video game, or guitar song will be all too quick to declare he's hopeless after one poor conversation. Whenever you can, try to remind yourself that you've succeeded elsewhere, and that you can get the hang of socializing if you approach it with the same mentality.