How do I tell my family about it without jeopardizing our relationship?

Wait for the time to arise itself. While in casual conversation try to create an opening in which you can then tell them straight out what is happening.

Parents tend to have a difficult time watching their children grow into adults. Remembering this is important when opening up to your parents. Sitting them down to talk as adults, helps show them that you are not only serious, but you care and love them. It hasn't always worked out for the best for me personally, but the more often I did it, the more I felt my parents respected me. Especially when I was able to express clearly what was on my mind. Making a list before hand helped me with saying the things I felt needed to be said. Hope this helps!

Good question but once again I really don't have a good answer for you to do that. Maybe try to look at more people and ask.

Thats a tough one. I haven't told any of my family yet, but I'm gonna start with my sister, then hopefully my parents when im in college

Depending on what, chances are, your family will understand most any situation. Whether it be sexual orientation, life choices, etc. they may be stunned at first, but with time chances are it'll all work out.

I need more information. Tell your family about what? Be open with them, honest is often the best kind of truth

My first recommendation would be to not lean to one extreme or the other. Attempting maintain some balance between extremes is important. Situationally, you can determine what that middle ground is. Once you have a middle ground, you can validate your families feelings. While it may be difficult in the moment, validation goes a long way. It can help to say things like, "I know you are feeling stressed about this and I understand that." Anytime you can reiterate what your loved one is feeling is an opportunity to strengthen the relationship. This can be a huge thing in your favor when having a tough conversation.