Over the course of one week five years ago, the U.S. financial system was brought to its knees. Throughout the show, I tell you where we stand five years after this momentous week, when it comes to jobs, income, housing, stocks and much more!

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To recap the action over that horrible 7-day period in September 2008:

• 4 investment banks vanished (Lehman Brothers declared bankruptcy, Bank of America swallowed the ailing and near-failing Merrill Lynch, and Goldman Sachs and Morgan Stanley were forced to become bank holding companies in order to access the government’s discount window)
• The government bailed out global insurance giant AIG
• There was panic in the money market fund industry after the Reserve Primary Money Fund “broke the buck,” dropping below the standard $1 per share valuation
• The Treasury Department introduced the first version of TARP, which was intended to grant the government the authority to purchase $700 billion of mortgage-related assets for two years.

Meanwhile, listeners were equally as interested in NOT repeating past financial mistakes. Margaret from MA started us off with a question about where to invest the proceeds of a CD that is coming due. Kevin followed up with a retirement planning question: how to create a stream of income from a $500K nest egg?

Joe from IN needs to access funds for his daughter’s education: which should he tap first?

Reeves from MO and John from KY are both in their 20’s and starting their first retirement accounts. We discuss their options and the advantages/disadvantages of 401 (k)s and Roth IRAs.

William from WI wrote in about a good problem: a large estate. If you are fortunate to have an estate larger than $5.25 million (for individuals) there are a number of options for addressing your potential estate tax.

Thanks to everyone who participated and to Mark, the BEST producer in the world. If you have a financial question, there are lots of ways to contact us:

• Call 855-411-JILL and we'll schedule time to get you on the show LIVE 

• Send an email: askjill@jillonmoney.com 

• Tweet me: @jillonmoney

A tepid August jobs report had little impact on "Jill on Money" fans, who were more interested in financial issues that hit closer to home.

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Joe from NY started the show, with a question about early retirement. Have he and his wife accumulated the assets ($2 million at retirement) necessary to call it quits at age 50?

Ron from NJ wants to know my opinion of the Social Security strategy called “File and Suspend” (sometimes referred to as “Claim Now, Claim More Later”)

File and suspend is a feature of the system can be useful for married couples, especially where one spouse has earned significantly more than the other spouse during their careers. In these cases, the lower earning spouse is usually better off claiming half of the spouse’s benefit because it is higher than the individual benefit.

File and suspend allows the primary wage earner to apply for benefits, then suspend collecting, while allowing the other spouse to start collecting spousal benefits immediately and then continuing to collect. Here’s the best part: the primary wage-earning spouse can wait to claim benefits until age 70, which increases the future individual Social Security benefit by eight percent each year between ages 66 and 70.

On the subject of Social Security and retirement income, Ang wants to make sure to factor in taxes when determining the proper amount to withdraw.

Robert from Buffalo is weighing whether or not to refinance an adjustable rate mortgage, while Scott from MO is trying to determine whether or not to pay off his outstanding mortgage.

Daud asked about the ratings of long-term care insurance providers. Finding any company willing to write LTC is difficult enough, but finding a highly rated one is even tougher. Check out the American Association for Long-Term Care Insurance for more information.

A few investment questions this week. One of particular note was from JG, who needs a plan to rotate a portion of his retirement funds into stocks. Meanwhile, John is worried about the future value of dollar-denominated assets.

Thanks to everyone who participated and to Mark, the BEST producer in the world. If you have a financial question, there are lots of ways to contact us:

• Call 855-411-JILL and we'll schedule time to get you on the show LIVE 

• Send an email: askjill@jillonmoney.com 

• Tweet me: @jillonmoney

Over the Labor Day holiday weekend, "Jill on Money" fans were working to prepare for what could be a volatile September. According to the Stock Trader's Almanac, September has been the worst month for stock performance over the past 50 years!

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Alex kicked off the show with a question about how to invest in bonds, while Jane followed up with concerns that perhaps her choice in a financial advisor might have been...well, ill-advised.

Rebecca and Jackie are looking for the best ways to pya down debt, while Linda is contemplating withdrawing money from her retirement account without generating tax liability.

Richard and Kane are receiving disability income, while Bill is trying to come back from a foreclosure

Stan and RJ are each weighing the purchase of an annuity to create a stream of retirement income, but in each of their cases, there are more affordable options.

Thanks to everyone who participated and to Mark, the BEST producer in the world...One question: what do Mark do to the intern to make her disappear on us? If you have a financial question, there are lots of ways to contact us:

• Call 855-411-JILL and we'll schedule time to get you on the show LIVE 

• Send an email: askjill@jillonmoney.com 

• Tweet me: @jillonmoney