One of my favorite ways is with a reality fair! Our event was even highlighted on this amazing Scholastic Blog: http://www.scholastic.com/teachers/top-teaching/2011/05/host-reality-fair
Reality Day/Reality Fair is a ton of fun. Trust me, your students will be talking. I love tying it into my career research units and college prep talks. Here's the basics on how it works:
1) The students research future careers/college plans.
2) The day of the fair you give them a register for a career (ideally the career they choose during their career exploration) and the average salary after taxes (include lots of CCSS by having them figure it out themselves). Need help with the math? There are lots of paycheck calculators online such as this one.
4) Sit back and try not to cry tears from laughing to hard. Seriously I've heard some great lines over the years such as these: "The real world is really mean, and I probably shouldn't, own a farm and have 2 kids."
Ready to create your own fair? Well lucky you, I created an event packet that has everything you need to recreate your own reality fair. Get it at my TPT store and enjoy. Be sure to tell us how it went!
Read more details about Reality Day here.