(MoneyWatch) If you're like most people who are approaching retirement, you've thought long and hard about the answers to these two questions:

- How much money do I need to retire?

- How can I generate a steady stream of income from my retirement savings that lasts the rest of my life no matter how long I live and what happens in the economy?

These are critical questions for most baby boomers who are planning for a retirement that could easily last 20 years or more. And that leads us to the most important question of all: When exactly can I retire?

These three questions have become particularly significant as companies continue to abandon traditional pension plans, meaning plans in which your employer takes responsibility for funding and paying you a monthly retirement income for the rest of your life. Without these safety nets in place, retirement planning now falls heavily on the shoulders of employees everywhere.

With the demise of pension plans, as an employee you're now much more likely to participate in account-based plans, such as a 401(k), 403(b), 457, profit-sharing or cash-balance plans. You might also have substantial savings in an IRA or regular investment accounts. And some of you might elect a lump sum, rather than monthly income, from a traditional pension plan, in which case you face the same challenges.

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With these types of programs, however, you're on your own when it comes to making your money last for the rest of your life. And when your money is exhausted, there'll be nobody there to bail you out, unless you have very generous relatives or friends. Many surveys show that employees approaching retirement are struggling with these issues and need help.

A tale of two retirees

I'd like to tell you two stories about people I know who've had to manage their own retirement savings. These stories contrast the potential outcomes of the challenge of managing your own savings and offer important insights about the strategies that will help you achieve your retirement goals.

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Your most critical retirement planning challenge