Since I've graduated college, I've had a lot of time to think about what the hell my life has been like for the past eight years. I'm actually really pleased with my high school and college experiences, but here's what I'd tell myself at 14 (just starting high school).
Dear 14 year old Lana,
Congrats! You made it out of eighth grade alive! The next few years are going to be integral to the rest of your life. So, take them seriously (you will), but not too seriously (you might). Lighten up! There's more to life than just studying. Make sure you make time for your friends and family.
Parts of high school are going to be great. You'll finally be challenged in your classes, which will be a big change from elementary school! Make sure to keep your head up, and don't be too hard on yourself when you don't get straight A's (you won't). Just keep doing your best (you will) and you'll be fine.
The kids you meet in high school will be pretty awesome. For the most part. There will be a significant portion of the school you may not want to interact with - but try. Some of them are very worthwhile people.
Don't be too frustrated with boys in high school. The fact that you haven't been kissed yet (at 14) is really not that big of a deal. It'll happen, and when it does, it'll be great. Don't get too upset at your first break up - it happens. Learn from it. Analyze what happened, what could have been better, and what was already good. Use that to guide your next relationship.
Even though you attend a Catholic school, don't let religion get the better of you. Eventually, you'll figure out a better way to live (non-religiously). Don't put too much stock in "eternal life." Try to be the best person you can - be loving, caring, and continue to nurture your desire to help others. Stay true to this ideal - it will be the guiding force in your life.
When you apply to colleges, pick one that's in the area, but not so close that you will have to live at home. It'll be healthy for both you and your parents if you move out; however, you can continue to build a strong relationship with your younger brother if you stay close enough so that you can see him regularly. Remember, he's about to be going through what you've gone through. Be there for him and lead by example - but be open to the idea that there ARE other ways, and encourage him to find his own way. He's a very talented guy.
When you start college, pick a major you love. However, DO NOT be afraid to change it! Experiencing something is always confirmational, but acknowledge the fact that it can be confirmed in the negative - as in, "I do NOT want to do that!" If you do decide to change your major in college, let it be your own choice (not your parents' choice or your friends' choice). Choose what really makes YOU happy, and keep in mind that it is your duty when you graduate college to find a job and support yourself. It's not Mom and Dad's job to support you indefinitely.
Once you get to college, don't be afraid to get out there and live a little. You'll be very focused on your studies, and eventually will encounter some financial issues. This will take a LOT of time, patience, and persistence to deal with, but don't give up. You'll make the right choice. Remember, however, that part of the fun of being in college is that you'll get to meet lots of new people and experience new things. So don't be afraid to go out to a party, or to introduce yourself to your new classmates or folks at the library. You meet the most interesting people that way.
Boys will be another story during college. You probably won't find anything too important until your senior year, so take some time to have fun (and be safe, of course!). You don't have to marry the first guy you date in college (thank goodness!), and as long as you're clear with how you want the relationship to go, get involved as much (or as little) as you desire. Remember NOT to commit to someone more than they're willing to commit to you. You love helping people, but keep this in check. You have a tendency to always put others' wants and needs before your own, but don't let this be a downfall at any point during college. Don't be afraid to walk away from a relationship when it turns into something with which you're unhappy.
Lastly, in college, build your connections wisely. Remember that you don't have to work in a field that's directly derived from your college major. You're creative, you'll figure it out. :)
Most of all, keep doing what you're doing, because looking back from age 22, your life is going to be pretty damn amazing. So brace yourself, honey, cause you're in for a wild ride.
Your present-day self.