10/10/23: We are at the point now where we are either going to push forward and put the pedal to the metal on our brokerage account, or max out our 403(b)s. What do you think?

10/9/23: Am I on track to have the option to retire in three years at the age of 62?

10/8/23: This weekend we're joined by Matt Abrahams, whose recently released book, Think Faster, Talk Smarter: How to Speak Successfully When You're Put on the Spot, will help you develop the life-changing ability to excel in spontaneous communication situations, from public speaking to interviewing and networking.

10/7/23: This weekend we're joined by Matt Abrahams, whose recently released book, Think Faster, Talk Smarter: How to Speak Successfully When You're Put on the Spot, will help you develop the life-changing ability to excel in spontaneous communication situations, from public speaking to interviewing and networking.

10/6/23: My wife and I had our first child, and we realize we will soon outgrow our one bedroom condo, and we're now looking to purchase a house. Can we afford both?

10/5/23: We have three rental homes and I'm wondering if we should sell them and invest in the market?

10/5/23: A financial advisor is suggesting I take $300k from my IRA and put it into a variable annuity. Do I need it?

10/4/23: How do you suggest we help our daughter pay on her $115,000 Grad PLUS loan that is restarting?

10/3/23: With retirement now just a few months away, my question is, do I need someone to manage my money?

10/3/23: I am currently contributing most of my 401(k) elections as Roth. My financial advisor told me to stop doing this and make all my contributions pre-tax. Is he correct?

10/2/23: With a lot of money sitting in cash, I can’t get past my fear of risk, or maybe it’s that I have very little tolerance for it.

10/1/23: This weekend we're joined by award-winning journalist Diana B. Henriques, bestselling author of The Wizard of Lies: Bernie Madoff and the Death of Trust. Diana joined us to talk about her latest book, Taming the Street: The Old Guard, the New Deal, and FDR's Fight to Regulate American Capitalism, a tale that takes readers back to a time when America’s financial landscape was a jungle ruled by the titans of vast wealth, largely unrestrained by government. Want more of Jill and Diana? Subscribe to Jill on Money LIVE to watch the full chat.

9/30/23: This weekend we're joined by award-winning journalist Diana B. Henriques, bestselling author of The Wizard of Lies: Bernie Madoff and the Death of Trust. Diana joined us to talk about her latest book, Taming the Street: The Old Guard, the New Deal, and FDR's Fight to Regulate American Capitalism, a tale that takes readers back to a time when America’s financial landscape was a jungle ruled by the titans of vast wealth, largely unrestrained by government. Want more of Jill and Diana? Subscribe to Jill on Money LIVE to watch the full chat.

9/29/23: I joined CBS Mornings to talk about what borrowers need to know before federal student loan repayments start back up in October.

9/28/23: With a new house purchase on the horizon, should we raid our brokerage account or take out a larger mortgage?

9/28/23: My husband and I are both full-time public school teachers and we are hoping to someday retire on our pensions. But will they be enough?

9/27/23: I am a working professional making good money, but I am considering getting an online MBA just to scratch my academic itch. Is it worth using a 529 plan?

9/26/23: I have recently gotten divorced and now I am house poor. How should I change things to make life a little easier?

9/26/23: With a mix of real estate, employee stock and inheritance issues on the table, I was hoping to get a review of our financial situation.

9/25/23: With retirement on the horizon, my major concern is account consolidation and how I can manage any potential tax burden.