(MONEY Magazine) – By the time he was in his early forties, Joshua Winston was ready to coast. He had already built a million-dollar veterinary practice in Long Island, N.Y., but he was also working upwards of 70 hours a week. So in 1997 he sold the practice and, soon after, moved to Arizona with his wife and infant son. He didn't think he'd ever need to work full time again: By the peak of the stock market boom, his net worth was $1.2 million and he had no mortgage or any other debts.

Then trouble. Winston and his wife divorced and subsequently divided their assets. And the stock market tanked. "When the crash came, it really hit me hard in some areas," he says. That's putting it mildly. Winston had hand-selected tech stocks like EMC and Sun Microsystems for his retirement fund in particular, which he says dwindled at one point to a paltry $30,000. After that, Winston ran for cover—and currently has more than $160,000, or 38% of his portfolio, stashed conservatively in cash. He also has a vet practice again, partly out of necessity but also because "I missed being a vet," he says. Now 50, Winston, a part-time stand-up comedian, says he wants to live comfortably, not extravagantly. He owns a modest house, which he shares half the time with his young son. But he wants to figure out how to recoup his losses. "My biggest worry is getting myself nearly back to where I was," he says.

To have a shot, he'll need to find a sensible way to become more aggressive, says Columbus, Ohio financial planner Peggy Ruhlin. Winston wants to whittle his cash stake to $100,000, and once he does that he'll have a total of $325,000 in the market. Ruhlin says that a little over 90% of that should be in stock funds. Winston owns a large number of similar large-cap funds; Ruhlin recommends selling those with the smallest capital gains (or, even better, capital losses) in favor of Meridian Value midcap fund and two small-cap funds—value-oriented Ariel and moderate Third Avenue Small-Cap Value—to balance an aggressive small-cap fund Winston already owns. Winston has 4% of assets overseas, and Ruhlin recommends he get that up to 20% by buying Oakmark International and Dodge & Cox International Stock. Since Winston has a big cash cushion, he can afford to take on moderate risk with his bonds to get a higher yield. Ruhlin suggests intermediate-term Dodge & Cox Income. —M.J.

Get Back in There Winston got burned in 2000 and has been too conservative ever since. By putting more in stock funds, and adding small-cap and midcap picks, he should be able to get growing again.

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