Jill on Money with Jill Schlesinger

Helping Mom Manage Her Finances

02 Apr 2025

Contributed by Lukas

I'm helping my mom (about to turn 80) manage her finances and I want to make sure I am helping her maximize her limited resources. Have a money questi...

Simplifying Inherited Accounts

01 Apr 2025

Contributed by Lukas

My father passed away last year and I inherited several accounts from him and now I need to figure out what to do with them. Have a money question? Em...

Variable Annuity With Death Benefit

31 Mar 2025

Contributed by Lukas

My insurance agent recently suggested a variable annuity with a death benefit. Yay or nay? Have a money question? Email us here Subscribe to Jill on M...

Federal Employee Recently DOGE'd

28 Mar 2025

Contributed by Lukas

I'm a federal employee who took the fork-in-the-road offer. I think we have enough retirement funds to make it but need some reassurance. Have a money...

Not Trying to Time the Market, But...

27 Mar 2025

Contributed by Lukas

It feels good to have avoided the recent market correction, but this only has value if I correctly time my re-entry. When do I pull the trigger and ju...

Funding a Real Estate Opportunity

26 Mar 2025

Contributed by Lukas

Can you help me determine the best option to purchase a piece of real estate without experiencing the biggest tax hits and also without having a mortg...

The Administration and a Market Crash

25 Mar 2025

Contributed by Lukas

Do you think it's possible that the new administration wants to take us into a recession on purpose? Have a money question? Email us here Subscribe t...

Allocating Cash Surplus

24 Mar 2025

Contributed by Lukas

With 12-15 years left until retirement, I want to be strategic about where to put our monthly surplus which is usually around $3,000. Have a money que...

State of the Economy with Diane Swonk

21 Mar 2025

Contributed by Lukas

With the first quarter just about in the books, I felt it was a good time for a heat check on where things stand, so I turned to Diane Swonk, the Chi...

On the Verge of Retirement

20 Mar 2025

Contributed by Lukas

I'm on the verge of retirement and looking for some guidance before I pull the plug. Have a money question? Email us here Subscribe to Jill on Money L...

Retirement Spending Check-Up

19 Mar 2025

Contributed by Lukas

We have a lot of money saved but it seems like we're spending a lot and we're starting to feel a bit concerned. Have a money question? Email us here S...

Feels Like We're Playing Catch Up

18 Mar 2025

Contributed by Lukas

My wife and I feel like we’re doing okay but we started saving for retirement and investing a bit late and are playing catch-up. Is there something ...

Should I Diversify My Financial Institutions?

17 Mar 2025

Contributed by Lukas

My wife and I, both in our mid-sixties, currently have over 90% of our financial assets in a variety of accounts held at the same institution. Do you ...

Ed Slott and the Five-Year Rule

14 Mar 2025

Contributed by Lukas

Here's a snippet from our recent webinar with the one and only Ed Slott. This is just five minutes, there's another 55 minutes of Ed behind the paywal...

Federal Worker Feeling the Uncertainty

13 Mar 2025

Contributed by Lukas

After working in higher ed for 15 years, I was able to find my dream job in the federal government, but recent events have left my personal and financ...

Unplanned Early Retirement

12 Mar 2025

Contributed by Lukas

I was laid off last November, an earlier retirement than I had planned, and now I'm wondering if I need to go back into the workforce. Have a money qu...

Can We Retire in 2.5 Years?

11 Mar 2025

Contributed by Lukas

With good money in our retirement accounts, and a few rental properties, I'm wondering if we'll be able to retire in roughly two years. Have a money q...

Help With the Big Picture

10 Mar 2025

Contributed by Lukas

I have been a lifelong saver and investor, and between my husband and myself we have accumulated a significant nest egg, yet I feel like I need help w...

Tune Out the Noise

07 Mar 2025

Contributed by Lukas

Academy Award-winning filmmaker Errol Morris turns his lens to an unlikely cast of upstarts who transformed the investment landscape in the documentar...

Should I Sell My DC Area Investment Properties?

06 Mar 2025

Contributed by Lukas

With the new administration firing so many federal employees, should I be looking to sell my investment properties in the DC area? Have a money questi...

The Gap Between Retirement and Social Security

05 Mar 2025

Contributed by Lukas

My husband and I have a plan for covering the gap between retirement and taking Social Security at 70. Is the plan solid? Have a money question? Email...

Should We Stay or Can We Go Now?

04 Mar 2025

Contributed by Lukas

We are at a crossroads, and while we think we have the savings to call it quits, we need a second opinion. Have a money question? Email us here Subscr...

On Track for Retirement at 65?

03 Mar 2025

Contributed by Lukas

I'm about to turn 60 and my plan is to call it quits in five years at 65. Am I on track to make this happen? Have a money question? Email us here Subs...

Early Retirement From Federal Service

28 Feb 2025

Contributed by Lukas

I'm a federal worker and have the possibility of accepting a voluntary early retirement. Given the current chaotic environment, I'm thinking I want to...

Additional Retirement Savings Advice

27 Feb 2025

Contributed by Lukas

Given that our retirement savings are so heavily skewed on the pre-tax side, I am wondering if increasing our Roth contributions is the right move. Ha...

Can I Take On More Risk?

26 Feb 2025

Contributed by Lukas

We both plan to work and invest until we are 70, and possibly beyond in part-time roles, so I am wondering if we can be a bit more aggressive for the ...

Moving From Saver to Spender

25 Feb 2025

Contributed by Lukas

We are just about to retire and the thought of spending the money rather than saving is a difficult shift. Any advice on how to make this transition? ...

Navigating Retirement in France

24 Feb 2025

Contributed by Lukas

Now that I'm living in France, I would like to review my financial situation and get some guidance on how to transition to living off my savings after...

Alternative Investing With Fundrise CEO Ben Miller

21 Feb 2025

Contributed by Lukas

Today we're joined by Ben Miller, co-founder & CEO of Fundrise, a real estate investment platform that uses technology to make high-quality real estat...

What to Do With Pension Lump Sum?

20 Feb 2025

Contributed by Lukas

My pension won't be coming for quite a few years, but I'm trying to plan now what the best course of action should be when the time comes. Have a mone...

Is Now the Time for Fixed Index Annuities?

19 Feb 2025

Contributed by Lukas

We found an advisor that we really like who claims to be a fiduciary, but he is suggesting we invest our "protected" money in fixed index annuities. S...

Can I Reduce My Savings Rate?

18 Feb 2025

Contributed by Lukas

My longterm plan of getting out of debt and having six months of emergency savings will be completed at the end of this year. Once that happens, can ...

Analyzing Deferred Comp Options

17 Feb 2025

Contributed by Lukas

My wife has a deferred comp plan that annuitizes if she stays with the company until the age of 60, otherwise all deferred comp is paid in a lump sum....

Romance Scams With Adam Levin

14 Feb 2025

Contributed by Lukas

This Valentine's Day we're joined by Adam Levin, cybersecurity expert and host of the What the Hack podcast. Adam joined us to talk about a plethora o...

Is Now the Time for Roth Conversions?

13 Feb 2025

Contributed by Lukas

With nearly a million dollars in tax-deferred retirement accounts, is now the time for us to consider some Roth conversions? Have a money question? Em...

Can I Quit in My 50s and Move to Europe?

12 Feb 2025

Contributed by Lukas

I'm wondering if I can retire in January 2026, just after I will have turned 57, and enjoy life in France. Doable? Have a money question? Email us her...

Can I Throw in the Towel?

11 Feb 2025

Contributed by Lukas

The idea of retiring and losing at least half my salary makes me nervous. Should I be or can I afford to do it? Have a money question? Email us here S...

Withdrawals in Retirement

10 Feb 2025

Contributed by Lukas

I need about $5k per month to live on in retirement but I'm not sure where I should be taking the money from. Have a money question? Email us here Sub...

Money Doesn’t Always Solve Anxiety

07 Feb 2025

Contributed by Lukas

I think my situation will lead to plenty of hate mail, but I'm also living proof that money doesn't always solve anxiety. Have a money question? Email...

How to Protect Assets From the Government

06 Feb 2025

Contributed by Lukas

How can I protect some of my assets if the government decided to take them away? Don't really rich people put money in the Cayman Islands or something...

I’m 56, Can I Retire in Three Years?

05 Feb 2025

Contributed by Lukas

I just turned 56 years old and am trying to determine if I can retire in three years. Have a money question? Email us here Subscribe to Jill on Money ...

Stock Price Movements

04 Feb 2025

Contributed by Lukas

I have a lot of money tied up in a single stock. If it goes up, yes, I am happy, but when it goes down, I think I should have sold. I check the accoun...

Am I on Target for Retirement?

03 Feb 2025

Contributed by Lukas

I'm 62 and looking to retire at 65, if not sooner. Can I do it? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jillonm...

On Track for Retirement at 55?

31 Jan 2025

Contributed by Lukas

We're currently in our 40s, but I am trying to figure out if my wife and I are on track to be able to retire at 55? Have a money question? Email us he...

Spouse Worried About My Retirement

30 Jan 2025

Contributed by Lukas

I would like to retire in June, however, my spouse is very concerned about finances and lacks confidence in the numbers. Have a money question? Email ...

Are We Saving Enough?

29 Jan 2025

Contributed by Lukas

I want to know if you think we are saving enough right now or do I need to be putting more away even though I will have substantial pension income? Ha...

Cash Out My Vested Pension?

28 Jan 2025

Contributed by Lukas

I have a vested pension from a previous career path that I can cash out now, or I can take the monthly payment once I reach retirement age. Which is t...

Where to Stash Home Sale Proceeds?

27 Jan 2025

Contributed by Lukas

I have one-million-dollars in proceeds from my condo sale and I’m renting for now. If I find a good deal, I could buy a new home or should we keep r...

How Much to Spend on New House?

24 Jan 2025

Contributed by Lukas

A new house is definitely part of the plan, but just how much to spend is still up in the air. Have a money question? Email us here Subscribe to Jill ...

Managing Massive Dividend Income

23 Jan 2025

Contributed by Lukas

My dividend income is now more than the salary I made during my working years. How can I manage the tax situation? Have a money question? Email us her...

Can I Pause Retirement Contributions?

22 Jan 2025

Contributed by Lukas

Am I okay to skip maxing out my workplace retirement contributions this year and use the same amount to rebuild my cash savings instead? Have a money ...

My Parents DO Need My Support!

21 Jan 2025

Contributed by Lukas

I just found out my parents have about 2-3 years of funds before they will run out of money. Their backup plan is me, and I'm trying to figure out how...

Should I Buy Into the Family Farm?

20 Jan 2025

Contributed by Lukas

We have the opportunity to buy into our family farm. Currently it is owned by my father/uncle/aunt and my uncle wants to sell his share. Should I buy ...

Investment Anxiety Entering 2025

17 Jan 2025

Contributed by Lukas

Given the unprecedented and potentially volatile environment we're entering in 2025, should I leave my money where it is? Should I pull some out of th...

Roth Conversions, How Much and How Fast?

16 Jan 2025

Contributed by Lukas

With over two million in tax-deferred accounts, and now that we're both retired, we feel now is the time for Roth conversions. How much should we do a...

I Have a Pension, Do I Need Bonds?

15 Jan 2025

Contributed by Lukas

Am I correct to treat my pension like "cash" and then put 100% of my other assets in riskier holdings? Have a money question? Email us here Subscribe ...

Roth IRA or Roth 401(k)?

14 Jan 2025

Contributed by Lukas

If I max out traditional contributions to my 401(k), it will lower my AGI and I'll be eligible to make Roth IRA contributions for me and my wife. Does...

Moving Parts in Retirement

13 Jan 2025

Contributed by Lukas

My wife and I are retired and we're trying to decide if we should start collecting Social Security and let our investments grow or should we take mone...

Can We Afford Our Forever Home?

10 Jan 2025

Contributed by Lukas

My husband and I have been eyeing a new subdivision in the suburbs and have fallen in love with one of the floorpans that would give us the space we n...

Can We Upgrade Our House?

09 Jan 2025

Contributed by Lukas

Will upgrading our house blowup our longterm financial plan? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jillonmone...

55 and Thinking of Retirement

08 Jan 2025

Contributed by Lukas

At 55 and approaching retirement, are we on the right track? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jillonmone...

Planning for Our Financial Future

07 Jan 2025

Contributed by Lukas

As I plan ahead for my financial future, am I doing it in the right way? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube:...

Anxiety Around My Finances

06 Jan 2025

Contributed by Lukas

With a history of financial anxiety, am I on the right trajectory? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jill...

529 Assets Not Growing

03 Jan 2025

Contributed by Lukas

With the market going gangbusters, why aren't the 529 plans growing? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @ji...

Am I Saving Too Much?

02 Jan 2025

Contributed by Lukas

With a big military pension on the horizon, am I saving too much in my retirement plan? Have a money question? Email us here Subscribe to Jill on Mone...

Happy New Year!

01 Jan 2025

Contributed by Lukas

Happy New Year from Jill and Mark! Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jillonmoney Instagram: @jillonmoney ...

Getting My Financial Life in Order

31 Dec 2024

Contributed by Lukas

After avoiding the issue for a while, I'm now trying to get my financial life in order. Have a money question? Email us here Subscribe to Jill on Mone...

Managing Cash Flow in Retirement

30 Dec 2024

Contributed by Lukas

I just retired at 57 and now I'm wondering how to tap the various accounts to generate a stream of income. Have a money question? Email us here Subscr...

Stacking Benjamins Part Two

29 Dec 2024

Contributed by Lukas

To close out the year, and to close out the weekend edition of Jill on Money, we're joined today and tomorrow by Joe Saul-Sehy, host of the Stacking ...

Stacking Benjamins Part One

28 Dec 2024

Contributed by Lukas

To close out the year, and to close out the weekend edition of Jill on Money, we're joined today and tomorrow by Joe Saul-Sehy, host of the Stacking ...

Should I Switch to Roth 401(k)?

27 Dec 2024

Contributed by Lukas

After years and years of pre-tax 401(k) contributions, is it time to make the switch to Roth? Have a money question? Email us here Subscribe to Jill o...

Nervous About Retirement

26 Dec 2024

Contributed by Lukas

I'm feeling a bit nervous as my husband prepares to retire. Do I need to worry? Have a money question? Email us here Subscribe to Jill on Money LIVE Y...

Merry Christmas!

25 Dec 2024

Contributed by Lukas

Merry Christmas from Jill and Mark! Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jillonmoney Instagram: @jillonmoney...

Combining Finances With My Partner

24 Dec 2024

Contributed by Lukas

I recently moved, switched jobs (internally), and am looking for help with finances as I try to combine my financial life with my partner. Have a mone...

Looming Tax Issues?

23 Dec 2024

Contributed by Lukas

I had assumed I would not draw from my 401(k) until I am required to take RMDs, but in listening to your show and talking to others, I’m questioning...

I'm 57, Can I Retire?

22 Dec 2024

Contributed by Lukas

I'm 57 and wondering if I have enough saved to retire sooner rather than later. Have a money question? Email us here Subscribe to Jill on Money LIVE Y...

Can I Retire in Three Years?

21 Dec 2024

Contributed by Lukas

We own our forever home and we want to renovate our kitchen, but we're nervous about spending the money and making a "dumb" financial decision as we b...

Can We Renovate Our Kitchen?

20 Dec 2024

Contributed by Lukas

We own our forever home and we want to renovate our kitchen, but we're nervous about spending the money and making a "dumb" financial decision as we b...

Feeling Ready to Retire, Am I?

19 Dec 2024

Contributed by Lukas

I feel like I'm in position to retire at the end of 2025 or in early 2026. Am I on track to make this happen? Have a money question? Email us here Sub...

Saving Our Son From Student Loan Hell

18 Dec 2024

Contributed by Lukas

Our son is trapped under some hefty student loans and we would like to help him out. Can we afford to do it? Have a money question? Email us here Subs...

Worried About Having Enough Money

17 Dec 2024

Contributed by Lukas

I've been saving for retirement for years and years, yet I'm constantly worrying about having enough money. Will I be okay? Have a money question? Em...

Time to Bring Assets Under Management?

16 Dec 2024

Contributed by Lukas

After coming into a very unexpected large inheritance, I feel that I might need assistance at this juncture, but I am unsure of what a reasonable mana...

The Future of Wealth Management Part Two

15 Dec 2024

Contributed by Lukas

This weekend we're joined by Marg Franklin, CEO and President of the CFA Institute. Marg joined us to discuss a plethora of topics, including the futu...

The Future of Wealth Management Part One

14 Dec 2024

Contributed by Lukas

This weekend we're joined by Marg Franklin, CEO and President of the CFA Institute. Marg joined us to discuss a plethora of topics, including the futu...

Helping Adult Children Now vs Later

13 Dec 2024

Contributed by Lukas

Should I help my kids out now while I'm still around, or should I just let them inherit whatever is left? Have a money question? Email us here Subscri...

Next Steps for Possible Retirement

12 Dec 2024

Contributed by Lukas

My employment is set to end in December of 2025 and I'm not sure where to put my money while I still have a job for one more year. Have a money questi...

Can We Upgrade Our House?

11 Dec 2024

Contributed by Lukas

We're considering a new home purchase, but the thought of doubling our monthly mortgage while cutting our monthly discretionary savings in half, is da...

In Need of a Decumulation Plan

10 Dec 2024

Contributed by Lukas

I believe we are set up for retirement, but need fresh eyes on our plan, especially when it comes to the decumulation phase. Have a money question? Em...

Can We Afford Two Homes?

09 Dec 2024

Contributed by Lukas

We have two homes and the plan was to sell one. My wife recently started discussing trying to keep both houses, which causes me concern about our fina...

In Our 40s and Planning for Retirement

08 Dec 2024

Contributed by Lukas

What's the best way for us to plan for retirement as we head into our early 40s? Have a money question? Email us here Subscribe to Jill on Money LIVE ...

Managing Lump Sum Payout

07 Dec 2024

Contributed by Lukas

I took a lump sum pension payout and now I'm responsible for managing the money, which has me a bit worried. Have a money question? Email us here Subs...

Roth Conversions and IRMAA

06 Dec 2024

Contributed by Lukas

When I consider doing Roth conversions, how much attention should I be paying to the IRMAA numbers? Have a money question? Email us here Subscribe to ...

Tax-Deferred 401(k) Problem

05 Dec 2024

Contributed by Lukas

Should I just drain my tax-deferred funds between 61 and 70 (storing the excess in a brokerage account) before I reach RMD age or just bite the bullet...

Feeling the Financial Pinch

04 Dec 2024

Contributed by Lukas

After a move, a house purchase, and two career pivots, we're feeling the pinch when it comes to our finances. Should we make some adjustments? Have a ...

When to Take Social Security?

03 Dec 2024

Contributed by Lukas

My husband is in good health, but he was adopted and we have no knowledge of his family history. Do you have a recommendation for when he should start...

Consumers Unnerved by Possible Tariffs

02 Dec 2024

Contributed by Lukas

The best news for the U.S. economy right now is the labor market's consistent growth, but what's worrisome is President-elect Trump's proposed tariffs...

How to Retire Part Two

01 Dec 2024

Contributed by Lukas

This weekend we're joined by Christine Benz, director of personal finance and retirement planning for Morningstar and author of the recently released ...

How to Retire Part One

30 Nov 2024

Contributed by Lukas

This weekend we're joined by Christine Benz, director of personal finance and retirement planning for Morningstar and author of the recently released ...

Social Security Elimination

29 Nov 2024

Contributed by Lukas

I work for the federal government and will be receiving a pension, but I also pay into Social Security and have never heard of a reduction in benefits...

Happy Thanksgiving!

28 Nov 2024

Contributed by Lukas

Gobble, gobble, happy Thanksgiving from Jill and Mark! Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jillonmoney Inst...