8/17/23: We're only in our 30s, but I want to make sure that we are actually on the right track towards retirement and not falling behind without realizing it.

8/17/23: As I approach my 37th birthday, I really want to get a better understanding of where my wife and I are on our financial journey. 

8/16/23: I was an early retiree failure, and now nearly four years later, I'm at the point where I am done. Will I fail again?

8/15/23: I recently inherited a traditional IRA and I have ten years to drain it. What should I do with the distributions, invest in a brokerage account or use a Roth IRA?

8/15/23: With the new rules on being able to roll $35k of a 529 into a Roth IRA after its been open at least 15 years, I was wondering if it might be a good strategy to start a 529 for myself to get the state tax benefits with the plan to eventually roll it into a 529?

8/14/23: I've been handling all my mom's finances for over a year now, and as we prepare to move her into an assisted living facility, we're not sure what to do with her house.

8/13/23: I'm newly retired and considering some Roth conversions, what should I be factoring into my decision?

8/12/23: With significant surplus cash flow each month, where should the funds be going?

8/11/23: If I can get better returns with CDs and high interest money market funds, and my managed brokerage account is essentially holding even, why do I even need a brokerage account?

8/10/23: I'm 65, still working, and would really like to retire by 67. Do I have enough money saved to make it happen?

8/10/23: My husband just got a new job, and we are thinking of moving to NYC in a few months, but I recently bought a condo in Denver. What should we do? 

8/9/23: I have $55,000 in consumer debt, yet I have plenty of assets, including plenty of accessible cash. Should I just wipe the slate clean?

8/8/23: I feel like I'm late to the investment game, so what should I be doing going forward in my 40s?

8/8/23: I'm considering buying into a small business, and while I am familiar with real estate loans, I'm not very familiar with SBA loans.

8/7/23: As we think about building wealth, what's the best strategy for us going forward? Real estate? Brokerage account?

8/6/23: We've all had the desire to travel through time and see what our lives will be like later in life. But while we want the best possible future for ourselves, we often fail to make decisions that would truly make that version of the future a reality. The recently released book, Your Future Self: How to Make Tomorrow Better Today, provides practical advice for imagining our best future so we can make that vision a reality. Author Hal Hershfield joins us this weekend to discuss. Want more of Jill and Hal? Subscribe to Jill on Money LIVE to watch the full chat.

8/5/23: We've all had the desire to travel through time and see what our lives will be like later in life. But while we want the best possible future for ourselves, we often fail to make decisions that would truly make that version of the future a reality. The recently released book, Your Future Self: How to Make Tomorrow Better Today, provides practical advice for imagining our best future so we can make that vision a reality. Author Hal Hershfield joins us this weekend to discuss. Want more of Jill and Hal? Subscribe to Jill on Money LIVE to watch the full chat.

8/4/23: Did I make a huge mistake by buying a fixed MassMutual RetireEase annuity from Fidelity?

8/3/23: We have been pretty good savers all of our working years but I'm still not sure if we're going to be okay in retirement.

8/3/23: In this fast paced housing market, should we consider changing our approach to be more competitive or be patient and keep looking?