Very often, when I need someone's help (be it a little advice or the need of an item, be it at the work or among friends, and so on) a feeling of stress comes over my mind.
I found out it has various reasons:
the fear of talking to someone,
the fear of looking weak, dumb or desperate,
and most often, the fear that other, irrelevant people also notice that I have a problem.
Since I'm quite sure I'm not the only one, I decided to ask: what is it possible to do against it?
Overcoming anxiety can be a long process requiring a great deal of introspection. This introspection is generally more effective when led by a trained therapist (Cognitive Behavioural Therapy in particular for anxiety).
However, overcoming anxiety in specific situations can be done. We must learn to :
recognise situations that make us anxious (as you have done in your question)
Learn tools to relax ourselves so that we can sufficiently distance ourselves from the anxiety to challenge our fears.
Challenge our fears, even if it is in our imagination that we challenge them.
You have already identified situations that you find anxiety provoking. So, once you recognise those occasions you can use techniques such recognising that your breathing has become shallow and slowing it down, taking deeper breaths, relaxing your shoulders, changing your posture. There are many such techniques that can be found online (if i find some good ones I'll edit and link here)
Once relaxed we can challenge our thoughts. When anxious situations can become distorted in our heads. For example someone anxious about germs may believe they will die from shaking someone's hand. This is an obvious distortion of what is likely to happen. So we recognise and challenge these beliefs. This can be done by looking at evidence for your anxious thoughts, and testing out the reality of negative predictions.
This does not only have to be done mentally, as this is a long process. It is possible to challenge these thoughts by conducting experiments. Observing others doing the same behaviour and seeing the evidence that nothing bad happens to them, before testing assumptions ourselves. We must weigh the pros and cons of avoiding the thing we fear and determine the realistic chances that what we're anxious about will actually happen.
From there we replace these negative unrealistic thoughts with more relalistic ones.
So. skipping the process:
Negative thought: People will judge me and think I am foolish
This is a distortion of being blown out of propotion.
Realistic replacement: People are more likely to understand and look for ways to be helpful as people like to be helpful. (evidence - the existence of stack overflow :P)
This is obviously difficult because you are replacing patterns of thought you have built up over your lifetime. However, if you can learn to recognise the triggers that create anxious moments and calm yourself then you can practice challenging them every time.
I am not a therapist This is best done with a therapist. I am aware there are many CBT self help courses online and a great amount of online documentation in this area. I cannot vouch for any of them. I get all my information second hand from my Significant Other who is a trained therapist. (giving you this information so you can evaluate this as a source information. I may get my SO to edit it for me)
Anxiety is similar to fears, you can't just wake up one morning, decide to "not be afraid of it" and carry on. Overcoming anxiety requires a fair bit of work, and approaching it in steps usually helps. These are just some steps I've thought of, but if you'd feel more comfortable doing other things that build up to your end goal, or want to do them in a different order that's what you should do, you know you best.
Ask someone for help with a task that's impossible for one person - For example if you're trying to lift something heave, or doing something that requires someone else to do something in order for the original task to be completed. You physically need their help, and you can't come across as weak seeing as they wouldn't be able to do it alone yourself.
Ask someone you know for help - Be it family, friends, or work colleges, asking them is often much better than asking a total stranger. If you tell them what you're doing/going through, they can often help make it better/easier for you.
Get someone else to ask for you - If someone else asks, you don't have to worry about the awkwardness of asking, but then if you help alongside them, meaning that they are effectively helping you. Simply by judging their response (or lack of) to helping you, you'll realize that they don't mind helping you, so there's no need to be worried about asking. You can even ask yourself if you have a friend/family there with you to help reassure you.
Go out and ask people for help - Similar to with spiders, you can't decide "I'm not afraid of them" and just not be afraid of them. At some point you'll have to cross the barrier, like swimming for the fist time, and just jump in there. The more you do it, the more comfortable you'll feel doing it. Just keep doing it more and more.
What's most important to remember is that most people really don't mind helping you, if they're too busy to help then odds are then they'll tell you why they can't. When I help people (or ask others for help), they often don't think of me as weak, and I'm sure with many other people that sort of thought is the last thing that may pop into their mind (and I'm sure they never do think of it).
This doesn't cover your whole question, but for technical issues, I like the 15 minute rule. I forget where I read it, but the gist is: if you take <15 minutes, you haven't really researched, but if you take >15 minutes, and you're on a team, you might be hurting the team.
Setting a time limit for searching for an answer before outright asking has helped me a lot. It helps take emotion out of the question.
Also, be confident you can follow up with "How can I look at things in the future to see the answer and not have to ask?" So you're not just asking how to do something, but you are showing you want to do better and more next time.
I've always struggled with social stuff, but in the last few years, I've been working on myself. The best thing I've learnt is to just do it. I used to struggle to say something because before it had left my mouth I'd overthought it and thought it was stupid, etc. The worst thing that can happen is they think what you say is stupid, or they just ignore it. If you force yourself to do the things that terrify you they won't bother you after the thousandth time, and you'll just get what you need to do, for example I'm terrified of height, so I'm going skydiving next month.
You need to do the thing before letting your mind talk you out of it. You could start by just asking strangers on the street for the time, then as you get more comfortable with that you ask for more, like directions or their thoughts on something.
"Just do it, make your dreams come true" - Shia LaBeouf
