Victor Guettlein, CFP®

Don't! The stock market is not a game; you don't "play" it. If you treat investing as a game, you will end up as a statistic. Rather, you should develop an investing PLAN around a set of financial GOALS. What you are trying to accomplish, the time you have to accomplish it, the amount you can save and already have saved, and the amount of risk you are willing or NOT willing to take, all combine together to produce a set of guidelines that will direct the type of investments you make. Your goals should direct your investments, not the other way around.

Yes; pixie dust! All investments, including "guaranteed" investments carry risk. That said, some are more safe than others. Many investors are buying annuities these days. While they may have principal guarantees, those guarantees are only as good as the company behind the guarantee, and if you examine the return proposition you will quickly realize that "safety" leaves you exposed to a loss of purchasing power, or "inflation". The best policy is to match your investments to specific goals, then create a well-balanced and globally diversified portfolio for your longer term investment goals - a portfolio that offers both offense and defense.

Alena, paying off high interest consumer debt is always a great idea! The only way to avoid short term gains, though, is to hold the stock for a year. If you have shares older than that, sell those first. Otherwise, my advice is that unless you are in a very high tax bracket, I wouldn't let the tax tail wave the dog; you'll probably be better off paying the tax and getting rid of the debt.