The retirement of previous generations reads somewhat like a fable: Once upon a time, individuals worked hard, bought a home, put children through college, amassed a comfortable nest egg, and passed along some wealth to heirs.

For millions of boomers, the housing bubble and stagnant economy seem to have made such a storybook ending virtually impossible. Instead, as the first boomers reached retirement age this year, a cautionary tale has emerged, and boomers are recalculating and reconsidering their options.

The boomer generation—those born between 1946 and 1964—is a force to be reckoned with at 78 million strong. With just the earliest of boomers reaching retirement age this year, the financial priorities of previous generations may seem very distant. Earlier generations, tested by the Great Depression, were generally more conservative with their spending and were participants in company pension plans, now becoming more rare. They also placed an emphasis on maintaining family wealth for the express purpose of passing it along to future generations.

Although boomers had an opportunity to accumulate great wealth over their careers, they also adopted extravagant spending habits, borrowing against ballooning equity in their homes and investment portfolios. As the housing bubble burst in 2008 and the markets took a steep dive, so did the lifetime savings of boomers. According to estimates by the Center for Economic and Policy Research, from 2004 to 2009, boomers between the ages of 46 and 54 saw their average net worth plummet 45 percent, while those aged 55 to 64 had their net worth cut nearly in half.

A slow-to-recover economy, now at risk for its second dip into recession, hasn't buoyed retirement portfolios. Throw in the needs of boomerangs—adult children returning home for support in a tough job market—and aging parents, and the boomer generation has experienced financial pressures from all sides. Today, leaving a legacy for future generations may be low on the list of priorities. Instead, boomers facing retirement may need to draw on all of their assets for future living and health care expenses.

For boomers with some distance to go before retirement, the recession's wake-up call is not one to be ignored. This is the time to take stock of retirement and other assets to determine if additional savings measures can and should be taken. During the next 10 years, we can hope that the markets and retirees' savings will rebound and more, but maintaining the status quo in terms of retirement contributions may not be enough. If your retirement is just a decade away, ask some key questions:

1. How much are you saving?

A survey by The Harris Poll earlier this year presented a distressing figure: 26 percent of those aged 46 to 64 had no personal savings and 25 percent had no retirement savings. While Social Security should provide some cash flow for boomers, it was never intended to be the sole source of retirement income. Take a close look at your spending habits to determine if and where cutbacks can be made without drastic alterations to your quality of life.

2. How much are you contributing to a workplace retirement account?

Many companies offer some sort of workplace retirement plan, such as a 401(k), and many match a percentage of an employee's contributions. For 2011, individuals can contribute up to $16,500 to their employer-sponsored plan; if an employer offers to match a portion of contributions, that's an additional boost to savings. Plus, for those 50 or older, the IRS permits employer plans to offer "catch-up" contributions, an additional amount— $5,500 for a 401(k) or $2,500 for a simple 401(k) in 2011—to be socked away with pre-tax dollars.

3. How much are you contributing to an individual retirement account?

Not everyone has access to a workplace-sponsored retirement plan, and fortunately, the IRS recognizes that many individuals must go it alone. Even if you have a 401(k), consider supplementing workplace savings with an individual retirement account. A Roth IRA won't provide immediate tax savings, but it will allow for tax-free withdrawals down the road. A traditional IRA can offer a tax deduction now, but you will be taxed on distributions; keep in mind that your tax bracket in retirement may be lower than your current bracket.

IRA contribution limits have increased in recent years, and for 2011, qualifying individuals age 50 or older can contribute up to $6,000, compared with $5,000 for the younger set. For two-earner households, each individual can open an IRA, if qualified; talk to your financial adviser to determine whether you're taking full advantage of the tax breaks.

4. How much is your property worth?

Capitol Economics recently calculated that home values have declined 33 percent from their peak in 2006, making a significant dent in boomers' net worth just as many are on the cusp of retirement. If you're relying on the equity in your home to pad your retirement nest egg, you may need to hold off on making a move. If you have adequate savings, consider leaving the equity untouched until home prices have had time to recover.

5. Do you plan to transfer any assets?

Leaving an inheritance is a meaningful undertaking, but given boomers' life expectancy and anticipated medical costs—estimated at anywhere from $200,000 to $500,000 after factoring in Medicare—it's important to use a practical approach. One option is to place assets in a living trust, ensuring that a benefactor's financial needs are addressed.

6. If you own a business, what is your exit strategy?

In addition to the complexities of retirement plans, distributions, Social Security, and Medicare, business owners have an additional challenge when it comes to exiting their organizations. The sluggish economy has taken its toll on many businesses, and the value of a company may not reflect what boomers have factored into their retirement plans. If profits have been low in recent years, the business simply won't fetch top dollar. Consider talking to an adviser to determine all the exit options, from a sale to retaining ownership with a less active role.

Every day, 10,000 boomers turn 65 and are faced with making a decision: retire or work. Many are opting to continue working in order to retain health coverage and pad their savings. While market volatility can spook near-retirees into moving all of their assets into ultra-safe cash vehicles, keep a long-term perspective about investments. Retirees can expect to live for 20 or 30 years in retirement, so some asset growth is still necessary.

While retirement portfolios can't be rebuilt in a day, boomers can improve their chances of an enjoyable retirement by taking some key steps. With planning, boomers may even be able to leave something of a legacy for their heirs, increasing the chances for a happy ending after all.