What does your retirement portfolio look like?

You've probably got a 401(k) or other workplace savings plan, and hopefully you've been contributing enough to collect your employer's match. And unless your plan has a "directed brokerage" option that lets you invest your savings in stocks, you probably have your money in mutual funds or in something that generally acts like a mutual fund, maybe with a name like "managed pool" or "separate account."

Something, in other words, where you aren't actually picking the stocks all by yourself. You direct your contributions into the asset class or investment style that suits your needs -- large-caps, growth stocks, small-cap value stocks, whatever -- and a pro manages the actual portfolio.

That's no accident. Study after study has shown that novice investors -- folks who don't take the time to learn how to choose stocks, and how to manage their investments in stocks -- tend to crash and burn when they "play the stock market."

Now, if somebody gets a $3,000 windfall and loses most of it while trying to pick stocks, that's not usually the end of the world. In fact, if that experience leads them to learn how to do it right, that $3,000 loss can end up being a cheap education.

Losses you can't afford
But if you lose a big chunk of your retirement fund, that's a different story. And this happens more often than you'd think to people with IRAs.

These days, many folks with IRAs have them at big discount brokerage firms like Charles Schwab (NASDAQ:SCHW) or E*Trade (NASDAQ:ETFC), where you can buy most any stock or bond or ETF or mutual fund you like.

When you change jobs and roll that old 401(k) balance into a Rollover IRA, you can end up with quite a hefty sum in that sort of account. In fact, some folks have most of their retirement savings in a Rollover IRA -- myself included.

It's very tempting to buy a whole bunch of stocks with that money. And this being The Motley Fool, and me being a stock-picking enthusiast, it's very tempting for me to tell you that that's exactly what you should do.

But the truth is, for many people it's a huge mistake. If you don't have a lot of experience investing in stocks successfully, it might be a mistake for you, too.

Picking stocks the right way
Compared to engineering an iPod, successful stock investing isn't all that difficult. But that doesn't mean it's easy. It takes knowledge, and discipline, and practice. And it takes self-knowledge, an understanding of one's own biases and bad habits, and the willpower to work around them.

Most people who are good at picking stocks acquired their skills via trial and error. The insight to have bought Apple (NASDAQ:AAPL) at $65 two years ago was acquired at the cost of having bought something like Juniper Networks (NASDAQ:JNPR) at $200 in the fall of 2000. And even then, there are plenty of good investors who bought General Motors (NYSE:GM) near $40 just nine months ago, when it looked like the company's turnaround was finally shifting into high gear.

A few clunks in the world energy markets later, and GM's at $11. Ouch. For most of those investors, life will go on. But if you had put a big chunk of your retirement portfolio in GM, thinking it was sure bet to double, that could have been a disaster.

Get it right the first time
When you take the time to learn how it's done, and you keep your emotions in check and make some good buys and hold them, it's a great feeling. Buying a stock like Contango Oil and Gas (NYSE:MCF) and watching it triple in a year? That's a blast.

Even if you've never bought a stock before, you can still safely experiment with stock-picking in your IRA -- if you're smart about it. How? In this month's issue of the Fool's Rule Your Retirement newsletter, available online at 4 p.m. today, lead advisor Robert Brokamp looks at this question in detail.

First, Brokamp recommends that you keep most of your retirement portfolio in mutual funds while you're learning your way around stock investing. The Rule Your Retirement model portfolios and fund recommendations provide an easy roadmap for doing just that. But it's OK to take a small portion of your portfolio -- 5% or 10% -- and invest in stocks directly. In fact, it's a good idea.

Brokamp also says -- and I totally agree -- that if you're going to take the time to learn to pick stocks, you might as well swing for the fences. Look for the next Apple, the next Microsoft (NASDAQ:MSFT) -- the small companies that will be tomorrow's global giants.

At the Fool, we call that Rule Breaker investing. This month's issue of Rule Your Retirement is focused on the ins and outs of Rule Breaker investing for retirement portfolios, complete with a how-to article and an in-depth interview with the Rule Breaker-in-Chief, Motley Fool co-founder David Gardner.

Even if you're totally new to stock investing, this issue will help you find your way to successful stock picking in short order. And if you're a stock market veteran, Gardner's exclusive insights are still worth a look. (Have you seen his track record?) Not a Rule Your Retirement member? Click with confidence -- a free 30-day trial gives you full access. There's absolutely no obligation to subscribe.