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.
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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.
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.
Let them fully state their point of view about the issue/conflict/problem without interruption. What do they feel people misunderstand about them? What do they want or expect from others?
The idea is to remain as neutral as possible. Just listening may be enough to allow someone to feel like they have the opportunity to say what’s on their mind.