How to Pick the Investment Strategy that's Right for You

Your most important investment decision is whether to pursue an active or passive investment approach:

With active investing your odds of succeeding range from 0 to 10%. With passive investing, your odds of winning are about 90% after taxes.

So which is right for you?

You can think of active investing as the classic "Buy Low and Sell High" investing strategy. It sounds right until we realize that we are buying and selling from other people who also think they are making a smart decision. And normally these other people -- the ones we are buying and selling from -- are very smart, capable and hard working. We've entered what economists call a zero sum game. In order for one party to win, the other must lose. Then it gets harder. It's not just a matter of half the players winning and the other half losing. Because buying and selling costs both money and taxes, many more people lose than win. After considering transaction costs, about 30% of the players win. After taking out taxes as well, the number of winners falls to 5% - 10%. The rub, however, is that if you do win with active management, you will make more money.

Passive investing is typically a "Buy and Hold" investment approach. It emphasizes diversification and keeping your investments for the long term -- usually decades. The beauty of this approach is that you don't need a sucker at the other end of the trade. Everyone who invests this way can win because as the stock market grows along with company earnings, everyone's investments go up. Because you are not buying and selling, your costs and taxes remain very low.

No one can tell you which approach to take. The answer depends on your appetite for gambling and whether you believe that the 5-10% who win are there by luck or skill.

Said another way: With a $1 million investment, would you prefer a 10% chance of making $120,000 or a 90% chance of making $100,000?

Beware the Roth IRA

... or at least the hype around the Roth. As you will soon learn, starting in 2010 anyone will be able to convert an IRA into a Roth IRA.

The brokerage firms see this as the opportunity of the year. As Fidelity excitingly promotes "With more than $1 trillion in IRAs ... advisers who get to their clients and prospects first ... will gain competitive advantage." The same thing is happening at all the big brokers ... the Roth is being actively promoted as a "no-brainer" for anyone with money to pay the tax now. Its highly likely that in the next few months some-one will try get you to convert your IRA to a Roth.

Simply put a Roth conversion allows you to pay all the tax on an IRA now and then withdraw the funds tax free in retirement.

The argument is that taxes will inevitably rise and so paying them now is just smart. While there are some cases where conversion makes sense, they are relatively rare among people with high current marginal tax rates.

The reason is that your high marginal rate - say 35% federal- is a function of you working and earning several hundred thousand dollars per year. In retirement you stop earning money - and your tax bracket plummets. If you retire with no more than $5 million in investments including IRA's - your federal marginal tax rate probably won't be much more than 15%. Rates would need to go up dramatically before conversion makes sense.

It is possible that you are a good Roth conversion candidate but its not a "no-brainer". Before converting make sure your adviser gives a detailed projection of your taxes in retirement and compare the rates to what you are paying now.