MoneyWatch with Jill Schlesinger

My rent is currently $1,800 a month and I am able to save $3,000 each month. Should I keep renting or look to buy?

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I keep hearing about retirement milestones and I'm spooked because I don't see myself reaching any of them.

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We're recently retired and trying to figure out if we have enough saved to make it work.

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Between my mother and myself we must have dozens of funds within our various accounts. How can we streamline things?

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

As we look to do a retirement reset, we're having a hard time making a major real estate decision.

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We’d like to have enough money for me to take three months off when our baby is born on top of the three months maternity leave I will be entitled to. Is this doable?

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I recently started a new job and have the option of taking some insurance coverage with me from the old employer. Should I take it?

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I am a high school teacher in my 29th year and I will turn 52 this year. I read The Great Money Reset and I think I may be ready to try a new career.

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

My wife and I both owned properties prior to getting together and have purchased another summer home that is now being gut-rehabbed. Should we keep all three?

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We are going to sell our home soon and will be left with a large chunk of money after paying off the mortgage. How can we best use the proceeds to fund our early retirement?

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

At 32 years old, it feels like I am very short on having enough saved to be able to retire. Not just to retire comfortably but to retire at all.

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I recently got a payout from a company I was a part of and now find myself wondering what to do with the money.

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I’m wondering if I should move money from my brokerage account to superfund our children’s 529 plans?

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

As I map out my long-term retirement game plan, I'm facing some questions regarding possible Roth conversions.

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

My husband will soon be 55 and wants to retire from corporate America and get another lower stress/fun job. Can he do it?

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

I'm a 37 year old separated dad of two currently going through a divorce and would like to get a check up to see if I'm still on track for retirement after this reset.

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Ever since I left my financial advisor in early 2023, I’ve become a bit obsessive with optimizing our financial situation. It’s obvious we’re in good shape for our age but how can I find a happy medium in managing our finances and not let it take over my life?

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

My husband of 34 years passed away about a year and a half ago. I am successfully on my feet working as a professional, maintaining our home and figuring out what the next steps should be. Am I on the right path?

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

We recently found out that my husband got a great job with a large tech company in Dublin, so we're trying to figure out if we should participate in the Irish pension option.

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

As I prepare to turn 40, I feel like it's a good time for my first real financial checkup.

Have a money question? Email us here

Subscribe to Jill on Money LIVE

YouTube: @jillonmoney

Instagram: @jillonmoney

Twitter: @jillonmoney

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.