For the last two years, I've done a virtual guest lecture to Jeffrey Brown's class in Maryland. Both times, I talked about how the skills they are developing with the web don't lock them into any one particular career. There are lots of ways to make money on the web. I felt somewhat qualified to talk about that, since I do a lot of them myself. Here are some of them.
Do what your parents did, get a job sir!
The most obvious way to have a career on the web is to get a job doing it. I think most high school and college kids, when they imagine themselves in the future working in web, imagine themselves at some kind of web "job". I begin with this, because it is the most obvious and definitely a solid path to consider.
At an agency
If you are a designer, put a portfolio together. Meaning, a website that is well done and showcases only your best work, and send it to agencies. Send it to agencies that say they are hiring as well as ones that don't. Get creative with the email that you send.
At a web company
It's not just agencies that hire web designers. All kind of companies have in-house web teams. This could be a "glamorous" fancy web 2.0 company, or it could just be the furniture warehouse off I-5 that is expanding its web presence.
How to find these "jobs"
One cool part about the web community is that we like to build our own tools for stuff. This includes exclusive job boards. If you are looking for a web job, might as well browse the places that solely list web jobs. Check out Authentic Jobs, Smashing Jobs, the 37 Signals job board, or Design Jobs on the Wall.
Some call it irresponsible to jump right into freelancing after college. They think working for an agency first is a better route, as you'll learn the ins and outs and fine tune your chops before trying to stake out on your own. I'm not sure I have that strong of a view. If freelancing strongly appeals to you, you have the drive and motivation to get better on your own, and you already have decent, well-rounded chops, then go for it.
This has been discussed a million times a million ways, but it is important to consider all the advantages/disadvantages to freelancing. With a job you get a steady paycheck, benefits, retirement, and a sizeable buffer from the nitty gritty details of buisness. With freelance, it's you and you alone in the trenches. Writing estimates, talking with clients directly, trying to get people to pay you on time, doing your own taxes, getting your own clients. Once you factor everything in, the glamour of freelance fades and the scale is a bit more evenly balanced. It will come down to personal/life factors more than anything else.
After you've launched a few eCommerce sites for clients, it may dawn on you that all this money that they are making, you could be making, if only you had something to sell. If you DO have something to sell, by all means harness your web skills to build a kick ass store and start selling it. There are some pretty designer-friendly design tools to help you through the stuff you wouldn't want to write from scratch, like processing credit cards.
Sell a product
Know how to make something? Know how to get something cheap you think you can sell at a higher price? Or know anybody you can partner up with who does either of those things? Sell it!
Sell a service
Outside of the web, people make money all the time with services. People will do your taxes for you, walk your dog, clean your house, just about anything. On the web, you need to find another need that people have and target that. If the need is strong enough, you can have them pay you to do it. This may be something distinctly webb-y like, host a website or manage your accounting, or something cool the web is particularly well suited for like connecting people to trade items or sending a fax. The sky is the limit here.
Writing / Blogging / Advertising
In the greater scheme of things, this is a pretty small niche. For most people, including myself, it's more side income than something a full-blown career. But certainly, there is money to be made through writing/blogging, via either just getting paid to write or through advertising.
The cool thing here is that the topic could be anything. You could start a blog or find a site to write for on just about any topic. Like to travel? Be a travel writer. Love World of Warcraft? Write about that. Know your geckos? Be a lizard blogger. I enjoy the story of Chloe Spencer who was barely a teenager and making huge bucks through Google AdSense blogging about Neopets, which I still have never heard of outside of her story.
I recently spoke at Herzing College to Michael Freiman's class and to Jeffrey Brown's class at Damascus High School. I'm sure both of them would agree that there needs to be more people like them. They teach students practical skills using today's methods. Certainly there are academic institutions out there that want to stay or get more cutting edge with their web curriculum. You could be their ticket!