1. Put your personal work out in the world so that it’s potentially vulnerable for negative comments. A video on YouTube, a piece of writing online – anything that can be complimented or critiqued, which will either boost your confidence or thicken your skin.
2. Do something over-the-top embarrassing to make a fool of yourself. Take part in a dance-off, test out cheesy pickup lines, make preposterous requests at restaurants.
3. Set a colossal ambition that will require you to discipline yourself and accomplish smaller goals first. e.g. Running a marathon that will require weeks or months of training.
4. Allow a friend to make plans for you, giving them creative control of a night filled with unknown festivities. Comfort is all about knowing what to expect and having limited surprises, this will be a unique change of scenery.
5. Read a book from a section you’d normally never set foot in. If autobiographies are normally your thing, check out a Teen-Fiction novel or Humor piece. Whatever is outside of the norm.
6. Perform some type of public speaking, such as a poetry or reading at an open mic night.
7. Pickup a new hobby that you currently have very little ability to do. Musical instruments, cooking, painting, writing, dancing, etc.
8. Go on an adventure and explore a surrounding city or an area you’re unfamiliar with, using no GPS or assistance from your phone. Enjoy being lost and getting around only by investigating for yourself, and asking others for directions.
9. It’s not always easy to express our feelings to the people we love the most. Make time for the people you consider yourself closest to, and vocalize your care for them, despite how much easier it can be to think “I love you” than to say it.
10. Go to a restaurant you’ve never actually been to and order something unique off of the menu. No cheeseburgers or salads, nothing you’ve had several times – and preferably something you struggle to pronounce.
11. If you’ve grown comfortable doing things solo, start doing those activities with a friend. If you only do things with friends, try going it alone. Trust me, seeing a movie by yourself is surprisingly pleasant.
12. Make a new friend. No – that doesn’t mean add a random person on Facebook! At work, in class or when you’re out, start a conversation IN PERSON, and make friends with someone.
13. Take an improv class to get comfortable with unscripted interaction which, most of life consists of.
14. Switch up your daily routine drastically. If you’re a night owl, try hitting the hay early and waking up at sunrise. If you’re an early bird, explore the wee hours of the night for a change.
15. Limit your television watching. Replace that newfound time being active and living your life, as opposed to watching others.
16. Take a financial risk that could result in a great reward.
17. Choose one of your fears and confront it head-on. Don’t like heights? Try skydiving, hiking a mountain or going on a rooftop – whatever you can do, as long as the idea of it makes you uneasy.
18. If at all possible, spend time around people more successful than you. Being surrounded by individuals who’ve accomplished more than you can be beneficial if used as inspiration and motivation.
19. Enter a competition in which the odds are stacked against you. Failure isn’t always a bad thing, especially if it’s utilized properly. By losing and feeling a letdown, you should become thirsty to try again or at least feel the glory of winning and success.
20. Say “yes” to every single opportunity that presents itself, big or small. From an invite to an event you typically wouldn’t attend, to a job promotion in a different city. Some things are life changers, and they should be embraced with open arms instead of shot down without consideration. 
