Part I: The limbo between high school and college

Singaporean students have about 9 months on average between high school/ NS and college. As far as I can tell, the most common ways to spend those nine months are:

1. Working as a relief teacher/ Teaching assistant. The MOE Teaching Internship programme is pretty good for those seeking this option. You get paid quite a decent amount and get CPF. Otherwise, you can approach a school directly and ask them if they need a relief teacher. It's a job most of you can do, since you've studied it all before and have a reasonable idea of what teachers need to do. It'll be fun to reverse the roles for once, after twelve years of being the student.
2. Being a tuition teacher. You can solicit on your own if you know people. If you can't get any requests, you can approach a tuition centre of sign up at independent tutor soliciting agencies such as Startutor. For the latter options, of course the agencies will charge a commissioning fee.
3. Working in a company as an administrative officer/ secretary. You'll need to be good at using computers such as microsoft windows applications.
4. Hospital Internships for medical school hopefuls.
5. Hospitality/ sales industry
6. Internships in an organization which deals with a subject you want to major in in College. Many organizations actually do take in high school graduates. Including certain law firms.
7. Some agency you want to get a scholarship from.

Brightsparks has a listing of possible jobs for high school graduates here.