I wish I had started preparing as early as you are! My best advice to you is to browse lists of boarding schools, pick a few that sound interesting, and then start doing research on them. Keep in mind that there are good schools outside of the super-prestigious New England loop-one of my favorites that I applied to was actually Episcopal HS in Virginia-that can sometimes be a bit easier to get accepted to. Once you have an idea of where you might want to go, request information packets from them (it was always exciting to find them in the mail!) and start working out the logistics of visiting, touring, and doing interviews. I recommend doing the tours and interviews pretty early on; that way, you’ve got a feel for the school by the time you start writing essays. Be straightforward in the interviews; though you might feel that you won’t seem impressive to these schools, chances are if you be yourself you have some unique interest that’ll set you apart. Plus, you still have plenty of time to volunteer, join a club, or even kick your school work into high gear and improve your grades. After the interviews, schedule a day to take the SSAT and start studying asap (I recommend using the SSAT website). Take one of the full practice tests early in the process, so you know what areas to focus on. Remember, if you bomb, you can always retake it. As for the essays-they may seem daunting if writing isn’t your strong suit, but if it’s not fine writing you can showcase, then showcase your originality. Try to think of an answer to the prompt that no one else could possibly write; you want to stand out, after all. Email coaches of any sports you play, send in a portfolio/video of any art you feel you are strong in, and stay in contact with the admissions officers. Anything you can do to make yourself stand out, do it.
Boarding school might be the right choice for you; it also might not be. Make sure that you want to apply for all the right reasons, and be aware of how much work the applications process is. This past year, I had to put far far more effort into preparing, writing and studying than into homework from all of my classes combined, so make sure this is something you really want to do. Since you need financial aid, your parents will also have to fill out their own application, so make sure that they are willing and ready to do so. No one in my family had ever applied to boarding school before, and we live in an area where it’s basically unheard of, so my parents and I entered the process pretty blindly about nine months ago. We did lots of research, overcame lots of hurdles, and I recently applied to Exeter, St. Paul’s, Hotchkiss, Taft, Lawrenceville and Episcopal. I truly feel that I did the best job I could have, and if I don’t get accepted anywhere, it just wasn’t meant to be. I encourage you to have this attitude if you apply; it has greatly eased my anxiety.
I know it seems like a lot, and it is, but don’t freak out if you really want to apply. Take it one hurdle at a time, and it’ll all fall into place if it’s meant to be. Best of luck!