(FORTUNE Magazine) – I am so nervous. In the April 1 issue I wrote a column called "Smart Man, Foolish Choices" about how I couldn't bring myself to invest in the stock market because I knew--or thought I knew--too much. I knew that, post-Enron, companies were about to go through the audit from hell and that we could still see a few unpleasant surprises. I knew that insiders weren't buying their own stocks, despite falling prices. And I couldn't bring myself to hand over my hard-earned IRA and 401(k) money to a mutual fund, which is as far as my stock investing can go because of possible conflicts of interest as a market journalist.

But I also said that what I wanted was cash on hand so that I could buy stocks on the cheap once prices crashed. Well, they've crashed--and then some! And that's just in the six months since my column ran. That's why I'm so nervous. With equity prices clobbered, it's time to put up or shut up. But when it comes to putting up, the Fred Mertz inside me doesn't want to part with a dime. It's not because I'm cheap! I'm worried because I really think we're headed for another round of bad audits, which are sure to hurt stocks even more. Yet I also know it's foolish to try to pick a bottom. And with a 15-year time horizon before retirement--that's more than a full business cycle--any coming near-term lows should be a distant memory by the time I get there. (Yeah, try telling that to people in Japan, who've been waiting nearly that long for a rebound!) Finally, I'm more concerned than ever about the prospects of all-out economic Armageddon, especially if the housing bubble bursts--when everybody who has been living off home-equity loans finds the equity wiped out. (When, you ask, did low interest rates ever cause a housing bubble to burst? When they rise, that's when!)

On the other hand, executives worth watching are starting to nibble on shares of their own companies. Or so says my insider-trading contact, George Muzea of Muzea Insider Consulting, who was so prophetic in my April column when he said that a true bottom in stock prices might not come until October (see "What Are Insiders Buying Now?" on fortune.com). At the same time, if we've learned nothing else, it's that the moment to buy is when everybody else is selling--and right now so many people have lost so much in the market that the last thing on their mind is buying stocks. I mean, look at the major indexes: All of them are lower by a long shot than they were when I switched jobs in April 1998 and rolled over my pension into a Schwab money market fund, earning a comfortable (and safe) 6%--entirely missing the bubble.

Those returns have now plunged to around 1%, which leads to the question: What's a know-it-all to do? Well, I always trust my gut, and my gut tells me it's time to start sticking my toe in the water--my little toe maybe, but my toe, nonetheless.

My wife, Mary, and I both like the concept of dollar-cost-averaging, so here's what we're thinking about doing: I'll shift 15% of the IRA into three funds. The first--we'll call this my international exposure--is the Matthews Asian Growth & Income fund (MACSX), which has been a surprisingly strong performer year-in, year-out, with average annual returns of 7.4% since it was started in 1994. When Americans think international, they still don't think Asia, even though that's where much of the real growth is. This fund, which has no exposure to Japan, focuses on high-growth markets like South Korea and Hong Kong. My second pick, and the aggressive mid-cap portion of my portfolio, will be the Olstein Financial Alert fund (OFALX). I'm willing to pay the steep 2.18% expense ratio and overlook my concerns about some of the fund's top holdings, including Merrill Lynch, because I love knowing that fund manager Bob Olstein, a former accounting professor, avoided the likes of Enron, EDS, and Tyco. I fully expect to buy more of the fund at lower prices. Finally, for some bond exposure, I'll take the large-cap Dodge & Cox Balanced fund (DODBX), run by a no-nonsense, disciplined management team that shuns publicity.

As for the remainder of my IRA: Another 45% will be earmarked for a laddered portfolio of CDs or Treasuries, with investments scheduled to mature yearly to minimize yield fluctuation. The rest will stay in cash for now, ready to buy incrementally when the S&P falls 100 points or the Dow falls 500 points--whichever comes first. (We'll call this the Greenberg modified dollar-cost-averaging plan.) My initial plan is to sit tight during whatever sucker rallies come between now and whenever, shifting to regular investments every quarter--maybe even more frequently--when I feel the market has been so wrung out that people simply don't care about stocks anymore.

My 401(k), sadly, is another story. I kick in the full allowable annual contribution of $11,000--but only because of the tax break. I don't like being held hostage to one or two fund families and just a dozen or so investment choices. But that's what I'm limited to with my company's plan. It's infuriating, and few if any of the funds fit the bill. So what am I really left with? Well, the Pimco Total Return fund (PTTAX), for one. But do I really want to invest in a bond fund when interest rates are this low? (Bill Gross may be a genius, but one thing that hasn't changed is the inverse relationship between rates and bond prices. When the Fed finally starts to raise interest rates, bond prices will inevitably drop.) Still, my bet is that rates are headed lower; remember, I'm in the Armageddon camp. And the fund is sufficiently diversified that, given my lack of choices, I'll give ol' Bill 10% but watch the fund's performance like a hawk. For stock exposure, I'm not sure any of the choices can, with consistency, perform better than the market as a whole. So I'll put another 10% into the Vanguard 500 Index (VFINX)--partly in deference to Vanguard founder and all-round good guy John Bogle--buying more as the indexes fall.

My plan sounds great on paper. But I'm still incredibly nervous, because I know one more thing: I'm going to lose money before I make it.

Herb Greenberg is a senior columnist for TheStreet.com. Questions? Comments? E-mail herb.greenberg@thestreet.com.