There's two ways to effectively "bring out a side of you you never knew existed." One is to go somewhere where you're not worried about being "judged." The other is to "fuck it" and just do it.
You must figure out based on your previous experiences and behaviors which people "hold you back" socially. This might be authority figures, people you consider similar to yourself, people which look up to you, or people who already know you a certain way and wouldn't want to see you change. These are the people who you feel "judged by," and who you wouldn't want to let down.
The first option is to distance yourself from these people for a while. So that you can try out a different personality. Perhaps a more outgoing personality when you're normally shy and introverted. Find other people who you can test jokes with and you wouldn't worry if the situation goes sour. Try new behaviors to see how people react. Explore how people unconsciously interact with each other.
The second option is to "fuck it." If you are sure you want to make a change and you feel like it doesn't matter anymore whether your current friends and family accept you or not.
If you want to test out a new personality and see how your own friends react to it. You can go ahead and be a different person. You can slowly ease into being a new person, or you can suddenly from one day to the other change personalities. Your friends will start to reevaluate your friendship, your family will start to question your choices. They might or might not be against it, you'd be surprised.
There's not a right and a wrong way to do it, as long as you intuitively follow the option which you feel suits you best.
Be different my friends.
Learn to control your intuition.
In order to create adventurous friendships,
explore the outdoors, and avoid being stuck in the house with nothing to do.