9/3/23: At 48, and hoping to call it quits at 55, I’m wondering if I’m on track and will I be able to retire in seven years?

9/2/23: 55 and just retired, but in need of some help with my portfolio allocation.

9/1/23: After receiving a lump sum from my employer as part of a separation package, how should it be invested?

8/31/23: Can I retire and spend some time with my husband who is already retired?

8/31/23: Given the current real estate market, and the fact that our house has appreciated significantly, I'm wondering if we should sell and become renters?

8/30/23: I’m in my early 50s, and after a recent inheritance, am I okay to retire now?

8/29/23: I’m 64 and would love to retire at 65, is this a realistic goal?

8/29/23: After a series of emotionally driven financial decisions, I feel like I need help getting back on track.

8/28/23: As I approach 50, how should I be maximizing my retirement contributions to possibly retire in five years or so?

8/27/23: What’s the best way to make a Roth conversion as clean and seamless as possible?

8/26/23: With an extra $1,500 of cash flow each month, where should it be going?

8/25/23: Given that we’re both high wage earners, and we have three kids, do you recommend whole life insurance as a way to invest for the kids?

8/24/23: Even though I know it’s the wrong financial move, should I still throw every available penny at my student loans?

8/24/23: I’m seriously thinking about going back to school and getting my superintendent credential and doctorate. Good idea or bad?

8/23/23: Thanks to a recent divorce and the death of my father, I'm in search of a money reset.

8/22/23: I plan on retiring in 20 months, and I’m breaking down everything like a maniac, yet I feel pretty lost. Am I positioned correctly?

8/22/23: I recently received a chunk of money via a bonus and I want to know if we should continue to invest in Vanguard or pay off some of the mortgage on our primary property?

8/21/23: My husband thinks we're just fine for retirement, I'm not so sure. Are we on track?

8/20/23: This weekend on the show we're joined by Dave Stachowiak, host of the popular Coaching for Leaders podcast, a show aimed at helping you discover leadership wisdom through insightful conversations. Dave joined us on our most recent webinar to discuss all things related to the workplace. Want more of Jill and Dave? Subscribe to Jill on Money LIVE to watch the full webinar.

8/19/23: This weekend on the show we're joined by Dave Stachowiak, host of the popular Coaching for Leaders podcast, a show aimed at helping you discover leadership wisdom through insightful conversations. Dave joined us on our most recent webinar to discuss all things related to the workplace. Want more of Jill and Dave? Subscribe to Jill on Money LIVE to watch the full webinar.