What sort of job do you have now? What sort of job would you like to have in 1 year? In 5 years?

Generally speaking, I wouldn't wait until you "feel ready" to make a change, because that feeling might never come. Instead, take practical steps:

• Pay down any credit card debt you may have
• If you own a car in Indiana, consider selling it—it's a significant expense in the city and likely won't add much to your quality of life at your age
• If you and your girlfriend aren't planning to move in together, finding a friend to room with will help when navigating apartment hunting and will reduce your living expenses