I had a modest portfolio that was guided by a traditional broker. He lost money for me every year. So finally I figured out that if he could lose my money, so could I and I started picking my own investments. I've never looked back.

The trick to making good investments is to make small investments at first. Get used to losing a little money. It's important that you don't get spooked after your fist 10% loss... or even your first 50% loss. I usually buy a small amount of a stock that I like and I'll buy more if I still like it later. Especially if the price goes down and I still believe in the company. The best time to buy is usually when everyone is selling.

A great way to get started "buying stocks" is to buy them with no money - Sign up for a free portfolio tracker at Yahoo finance or Marketwatch. It's free. You can add stocks with phantom purchases and "buy and sell" to your hearts content. After a couple weeks, you can see if you like it. Spend a few months doing this, you'll eventually get the hang of it. Use real investment amounts that you might make.

When you do finally decide to invest, make sure to only invest what you can afford to lose and you'll be ok.

Oh... BTW. These are great books. I'd buy and them before you start. They won't teach you how to invest, but they will show you the psychology behind investing, which I think is more important.
http://www.amazon.com/Reminiscences-Stock-Operator-Investment-Classics/dp/0471770884
http://www.amazon.com/Confessions-Street-Addict-James-Cramer/dp/0743224884/ref=pd_sim_b_4

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