I really enjoyed this TED Radio Hour episode about getting outside of your comfort zone. My big takeaway was from the interview with Tim Ferris. He offered a wonderful writing exercise for risk-taking and processing your fears.
On the first page, make three columns:
Define: Name all of your fears/negative outcomes around a specific risk you might like to take. Be very specific and list everything you can think of.
Prevent: Look at each of the fears and consider if there is any action you could take to prevent the negative outcome. List any and all ideas.
Repair: Look at each of the negative outcomes and think about how you might be able to repair the problem and mitigate the negative outcome if it actually happened.
On the second page, write all of the benefits of taking actions.
On the third page, write all the costs of inaction.
Pretty straightforward! But it always amazes me what writing things on paper in black and white can bring up! I am a worst-case scenario thinker, so this helps me realize how silly some of the fears in my head are!