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Make yourself step outside of your comfort zone by removing your usual precautions.
If you typically interact through e-mail or shop online, try picking up the phone instead. Once you are comfortable doing this, take care of business in person.
Find something you are good at doing, and do it. Finding a hobby in which you excel will help you because it relieves stress and builds confidence. You will then have an escape on those bad days when it feels like nothing is going your way.
Visualize the things that you like or admire and stop looking at yourself so critically. You are likely to be the only person who judges you so harshly.
Try to gradually overcome your tendency to feel insecure by introducing yourself to those situations slowly - as a sort of desensitization process.
If you have trouble in social environments, for example, ask trusted friends or family members to go with you and act as a buffer.
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