Good luck, Meg. You’ll need it.

October 13, 2011, 4:40 PM UTC

By Kevin Kelleher, contributor

FORTUNE — Most seasoned executives have their share of career ups and downs. And then there’s Meg Whitman.

Whitman presided over eBay’s rise from a scrappy startup to an e-commerce giant worth $75 billion — then presided over a decline that struck $30 billion out of that market cap. She joined Goldman Sachs (GS) board, but soon resigned after receiving shares of IPOs Goldman underwrote. She spent $144 million in a gubernatorial campaign, only to finally admit, “We’ve come up a little short.

In January, she resurfaced as a new director of Hewlett-Packard (HPQ), joining a board that has become one of the most questioned in the history of Silicon Valley. That same board circumvented its nomination process to name her as HP’s CEO. While some question whether she is the right leader for HP now, the real question may be can HP be fixed at all? Is Whitman setting herself up for failure simply because turning HP around may be a thankless task?

So far, Whitman seems to be making the right initial moves. She took a Steve Jobs-like annual salary of $1. (Plus lots of options.) She vowed to address this month the biggest immediate question facing the company: whether to sell off the PC business. She hired an investment bank to defend itself any activist investors who may demand the company be broken up. (That bank was, yes, Goldman Sachs.)

In the three weeks since HP announced Whitman would become CEO, its stock has risen 10%. But it’s still down nearly 50% in a little more than 8 months. It’s too early to say whether HP is rising because of the kind of technical bounce that follows a precipitous drop, or because investors have recognized it’s trading at bargain-basement levels: Five times its earnings (the S&P’s ratio is 14) and 0.39 its annual sales.

To listen to analysts and investors, though, the road ahead for HP is a rough one. “It’s a big, complicated mess,” said hedge fund investors Bill Ackman, who had recently visited the HP campus. “It was depressing walking around there.”

Mark Moskowitz, an analyst at JPMorgan (JPM) said last week he expects HP to continue to underperform its peers in revenue and earnings growth. Moskowitz said HP may be cheaply valued, but is still unattractive because of the “chronic downside” of its earnings potential. Furthermore, he notes, when big-tech turnarounds do work, they are slow and painful. “There are few examples of value stories in large cap technology where high-profile turnarounds both worked and occurred in short order. We can name only two that worked, IBM (IBM) and Apple (AAPL), but both of those took more than five years to achieve positive outcomes. HP is just entering year two, implying more pain ahead.”

Others seem to agree. Citigroup’s (C) Richard Gardner, cutting his price target from $45 to $28, pointed to declines in server revenue and tablet cannibalization of HP’s personal computers. But as Barclays (BCS) Ben Reitzes pointed out, “the software and services businesses have not yet been optimized to a point where the company can live without PCs.” So PCs are HP’s albatross, but an albatross it needs around its neck.

Beyond a sale of the PC business, it seems there’s little Whitman — or anyone — can do to revive earnings growth in the next year or so. HP can help companies get into cloud computing, but that was one of Léo Apotheker’s big initiatives during the 11-month tenure that led to his firing. Another campaign was the TouchPad tablet, which saw disappointing sales. Then again, which company not named Apple has seen tablet sales that didn’t disappoint?

As a recent board member, Whitman has the support of the board and is likely to act on its ideas. But HP’s board is one with poor instincts in managing crises. It’s a high-profile tech turnaround attempt, like Yahoo (YHOO), that chews up and spits out experienced CEOs. In six years, the company has fired three CEOs — with experience leading Lucent, NCR Corp. (NCR) and SAP (SAP) — and now it’s hired one who once led eBay . And the stock is still trading at the same price as it did 15 years ago. In other words, Whitman should enjoy her ascendancy to the CEO’s desk. What comes next is likely to be much harder.

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