If you're struggling with severe shyness and want to break free from your shell, you're taking a step in the right direction to reach that desire, just by viewing this article.
I have been shy my whole life, and have always referenced myself as being a shy introvert. That's mistake number one. Adding a label to yourself restricts what you allow yourself to be and limits you to a standard that you may not necessarily favor. For example, part of me has always wanted to be more easygoing and put myself out there. But I've held back and blamed it on my shy personality.
Your thoughts are very powerful. What you think about yourself greatly influences your actions and shapes the person you become. So the first step to overcome introverted ways is to break the pattern, cut the label, and re-wire your brain. "I don't want to be shy, therefore I won't be." That is what I tell myself when walking into a social situation. It provides a sense of power, confidence, and self-assurance. Confidence is key when engaging in conversation, and most people are naturally drawn toward that confident persona. People are also attracted to those who radiate positivity, so don't forget to smile!
So you've decided that you no longer want to be a shy, reserved individual. What now? How do you become more outgoing when you have little to no social skills? Practice. For me, I actually looked to YouTube to learn a few social skills, conversation starters, and even flirting tips. I came across a man named Matthew Hussey, who has uploaded hundreds of videos and published many books on the topic of "how to get the guy." He gives advice on not only how to make a guy interested in you, but also on various other topics including how to start and keep conversations. I highly recommend looking into his channel if you're struggling to be more outgoing or make the first move. I became inspired watching these videos, so I picked up a few skills and put them into practice.
There are countless ways to start a conversation, and it all depends on the setting, who you're trying to talk to, and the motivation or reason why you want to talk to this person. You don't want to overthink a conversation too much, though. You may want to have some sense of control, but don't edit your thoughts so much that you don't get the chance to voice them. Once you engage in conversation, you don't have to stick to routine. For instance, you may ask someone what their occupation is. Instead of replying with a vague response, ask further questions about what their job entails. Allow them to talk about their expertise. That lets them know that you're truly interested and engaged. Plus, people love to talk about themselves, especially to someone who wants to hear about it. It also makes you appear as an interesting and curious individual, which is attractive.

Now I know this article is about how to not be shy, but that is not to say that being shy is a negative quality. Being shy is simply a personality trait that some people are comfortable with and some are attracted to as well. But for those of you who long to break free from your shell, my advice to you is: don't restrict yourself with a label, seek guidance, step out of your comfort zone, initiate conversations, even if its simple small talk, and do it with a bright smile on your face that radiates confidence.