Market timing sounds so simple and elegant; however, I think it pays to remember that it takes not one, but two correct market calls to be successful at it. You’ll have to sell before the markets fall and buy before they rebound, which I can almost guarantee they will once the dust settles.

I’ll leave that to the professionals, thank you very much. But how do I know when to buy stocks?

Strategy 1: Save up a set amount each year, and buy once in bulk.
On paper, this stock investing strategy seems like it’s guaranteed to yield the highest return because you’d ideally be buying when prices are lowest every year, and letting your profits run through bullish trends.

But keep in mind that a strategy like this is easy to produce on paper because in hindsight, we already know when the lowest point was for each year. In the day-to-day, there’s no way you can know if the next day will bring a bull or bear move in the markets, much less whether it’s the top or bottom for the year.

In this hypothetical, the investor buys as many shares of SPY as possible with $2,000 on the first trading day of the year. I didn’t take into account the “change” carrying over from year to year.

Strategy 2: Buy a set dollar amount each month to average your cost basis.
This is probably the easiest stock investing strategy for a novice to get accustomed to a disciplined strategy. But it’s not the most lucrative, because by definition, “averaging in” means some months you’ll be buying when prices are overvalued, and some months you’ll be buying a bargain.

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