Jill on Money with Jill Schlesinger

Estate Planning Conversations Part One

11 May 2024

Contributed by Lukas

There are three basic steps to getting started with the estate planning process. First, you’ll need to get organized by documenting all your assets....

Are the Managerial Fees Worth It?

10 May 2024

Contributed by Lukas

I currently have a financial planner who charges me an annual percentage of the portfolio. This amount is always on my mind. Are there people who are ...

Planning for Retirement

09 May 2024

Contributed by Lukas

This year, a record number of Americans are expected to retire, but a new study reveals that a majority of Americans turning 65 in the coming years ar...

Help Navigating Retirement

08 May 2024

Contributed by Lukas

We're both already retired but looking for some advice as we prepare to navigate the next few years. Have a money question? Email us here Subscribe to...

Can We Pause Retirement Savings?

07 May 2024

Contributed by Lukas

Is it okay for us to press pause on retirement for a year, or maybe two, so that we can start saving for a house down payment? Have a money question? ...

Should I Stay or Should I Go?

06 May 2024

Contributed by Lukas

I'm miserable at my job. Can I retire now or should I keep plugging away for a bigger pension? Have a money question? Email us here Subscribe to Jill ...

Work, Retire, Repeat Part Two

05 May 2024

Contributed by Lukas

This weekend we're sharing a snippet of our recent chat with professor, labor economist and author Teresa Ghilarducci, who joined us to chat about her...

Work, Retire, Repeat Part One

04 May 2024

Contributed by Lukas

This weekend we're sharing a snippet of our recent chat with professor, labor economist and author Teresa Ghilarducci, who joined us to chat about her...

Where to Park Emergency Fund

03 May 2024

Contributed by Lukas

Our emergency fund is in a bank savings account with an interest rate of 0.02%. Is there a better place to park the cash? Have a money question? Email...

Roth 401(k) or Not for High Earner?

02 May 2024

Contributed by Lukas

With a huge chunk of pre-tax money in my 401(k), I am worried about what the future RMD will be. Should I start using the Roth option? Have a money qu...

Retirement Planning With a Pension

01 May 2024

Contributed by Lukas

How should we factor my pension into our overall retirement picture? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @ji...

Can I Manage My Own Money?

30 Apr 2024

Contributed by Lukas

After getting hit with some large tax bills from our managed account, is it time to manage it on my own? Have a money question? Email us here Subscrib...

Okay After Forced Retirement?

29 Apr 2024

Contributed by Lukas

After retiring a tiny bit earlier than expected, am I okay as is? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jillo...

Can I Retire Securely?

28 Apr 2024

Contributed by Lukas

With retirement in the near future, have I accumulated enough to call it quits in a secure fashion? Have a money question? Email us here Subscribe to ...

Account Consolidation

27 Apr 2024

Contributed by Lukas

After changing jobs several times over the last decade, I find myself in need of some account consolidation. Have a money question? Email us here Subs...

Considering Retirement at 62

26 Apr 2024

Contributed by Lukas

As I'm set to turn 62, I'm thinking about retiring. Can I do it? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jillon...

Can We Build Dream Home

25 Apr 2024

Contributed by Lukas

With a bunch of money sitting in cash for a potential home purchase, should we leave as is, or invest it? Have a money question? Email us here Subscri...

What’s the Best Financial Move for Us?

24 Apr 2024

Contributed by Lukas

We think we are in good shape to be fully retired in about two years but we're not totally sure. What do you think? Have a money question? Email us he...

Overall Retirement Preparedness

23 Apr 2024

Contributed by Lukas

I'd love to get your thoughts on how I am poised for retirement, if there is anything I am missing and/or should be doing differently? Have a money qu...

Unknown Future After Sudden Divorce

22 Apr 2024

Contributed by Lukas

I'm looking for advice on how to invest for my next chapter since my life completely changed after a gray divorce that was unexpected and moved very f...

Considering Retirement in Two Years

21 Apr 2024

Contributed by Lukas

After working in IT for 28 years, I'm considering retirement in the near future. Can I do it? Have a money question? Email us here Subscribe to Jill o...

Should We Switch to Roth?

20 Apr 2024

Contributed by Lukas

With pensions in our future, and a good chunk of pre-tax savings, should we make the switch to Roth contributions? Have a money question? Email us her...

Did We Make a Big Mistake?

19 Apr 2024

Contributed by Lukas

With interest rates so high, did we make a huge mistake by purchasing a new home? Have a money question? Email us here Subscribe to Jill on Money LIVE...

We’re Both Retiring and Feel Lost

18 Apr 2024

Contributed by Lukas

Both my husband and I are retiring this year and we could really use your expertise with several of our questions. Have a money question? Email us her...

My Next Phase of Life

17 Apr 2024

Contributed by Lukas

I am good at saving and living within my means, but I don't know when to pivot so that I can start to lessen that pathway and move into the next phase...

Oil and the Economy

16 Apr 2024

Contributed by Lukas

I joined CBS Mornings with a look at the potential disruptions to the global economy, including impacts on oil markets after Iran's unprecedented laun...

Can I Leave My High Income Job?

15 Apr 2024

Contributed by Lukas

Can I leave my high income job in two to three years and live out my dream of traveling? Have a money question? Email us here Subscribe to Jill on Mon...

Evaluating Pension Options

14 Apr 2024

Contributed by Lukas

As I consider whether or not to turn on my pension, which option should I choose? Have a money question? Email us here Subscribe to Jill on Money LIVE...

Lower Income Tax Strategy

13 Apr 2024

Contributed by Lukas

With my income down for a short period of time, what should my tax strategy be? Have a money question? Email us here Subscribe to Jill on Money LIVE Y...

Can I Retire Early?

12 Apr 2024

Contributed by Lukas

I would like to leave my corporate role and focus on pursuits that likely won't generate any income. Can I do it? Have a money question? Email us here...

Withdrawal Strategy Planning

11 Apr 2024

Contributed by Lukas

I'm facing my first RMD this year without any withdrawal strategy planning. Am I stuck with this enormous RMD that has affected my income tax and will...

Do I Have Enough Saved?

10 Apr 2024

Contributed by Lukas

According to all the financial calculators, I'm behind in terms of saving for retirement. Are they accurate? Have a money question? Email us here Subs...

To Roth or Not to Roth?

09 Apr 2024

Contributed by Lukas

I am wondering if it's worth it to change my contributions to put more into a Roth, and if so, should I put it into my work Roth or my Vanguard Roth? ...

In Our 30s and Planning for Retirement

08 Apr 2024

Contributed by Lukas

My wife and I are both 32 and we're wondering how we should be approaching our retirement planning. Have a money question? Email us here Subscribe to ...

Slow Productivity Part Two

07 Apr 2024

Contributed by Lukas

This weekend we're sharing a snippet of our recent chat with Cal Newport, bestselling author and one of the world’s top productivity experts, who jo...

Slow Productivity Part One

06 Apr 2024

Contributed by Lukas

This weekend we're sharing a snippet of our recent chat with Cal Newport, bestselling author and one of the world’s top productivity experts, who jo...

Got Laid Off, Can I Retire?

05 Apr 2024

Contributed by Lukas

I’m 60 years old and was recently laid off, which has given me the chance to review our finances and consider retirement. Can I do it? Have a money ...

Competing Financial Needs

04 Apr 2024

Contributed by Lukas

With competing financial needs, including a wedding and student loans, where should the focus be? Have a money question? Email us here Subscribe to Ji...

Intergenerational Financial Issues

03 Apr 2024

Contributed by Lukas

After trying to do the right thing, we find ourselves facing an uncomfortable intergenerational financial issue. Have a money question? Email us here ...

Sweet Spot for Roth Conversions

02 Apr 2024

Contributed by Lukas

Is there a sweet spot to shoot for with regard to taxes and IRMAA surcharges when doing Roth conversions? Have a money question? Email us here Subscri...

Part of Recent Tech Layoff

01 Apr 2024

Contributed by Lukas

After being laid off I'm preparing to start a new job and want to make sure that we're on the right financial path as we start a new chapter. Have a m...

Use 401(k) or HSA?

31 Mar 2024

Contributed by Lukas

Should I be focused on maxing out my 401(k), or should I redirect some of my contributions into an HSA? Have a money question? Email us here Subscribe...

Recently Retire, Is My Future Secure?

30 Mar 2024

Contributed by Lukas

Now that I'm already retired at 51, is my financial future is solid shape? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTub...

Overwhelmed by Student Loans

29 Mar 2024

Contributed by Lukas

With a tremendous amount of student loan debt, what's the priority, saving for retirement or trying to pay down the debt? Have a money question? Email...

Laid Off, Can I Retire?

28 Mar 2024

Contributed by Lukas

I'm 59 and was recently laid off, and now I'm wondering, do I really need to look for another job, or can I retire? Have a money question? Email us he...

Maximizing Your Tax Refund

27 Mar 2024

Contributed by Lukas

As the tax season progresses, the IRS reports having received over 71.5 million tax returns, already issuing more than 49 million refunds to Americans...

Roth Conversion Scenario

26 Mar 2024

Contributed by Lukas

With a lot of money in pre-tax retirement accounts, am I overthinking the possibility of doing Roth conversions? Have a money question? Email us here ...

Can I Trust What the Advisor Told Us?

25 Mar 2024

Contributed by Lukas

When we look at the numbers the financial advisor gave us, we realize now that we don't really understand them. Can we trust what she told us? Have a ...

The Bankers’ New Clothes Part Two

24 Mar 2024

Contributed by Lukas

This weekend we're joined by Anat Admati, co-author of The Bankers’ New Clothes: What’s Wrong with Banking and What to Do about It. New bank fail...

The Bankers’ New Clothes Part One

23 Mar 2024

Contributed by Lukas

This weekend we're joined by Anat Admati, co-author of The Bankers’ New Clothes: What’s Wrong with Banking and What to Do about It. New bank fail...

Cash Heavy, What to Do?

22 Mar 2024

Contributed by Lukas

I think we are very cash heavy but I'm also not worried about where we are for retirement, so I would like to pay off our mortgage. Yay or nay? Have a...

Pay Off Mortgage With Windfall?

21 Mar 2024

Contributed by Lukas

With a large windfall coming our way, should we pay off the mortgage or invest in a brokerage account? Have a money question? Email us here Subscribe ...

Can I Retire Now?!

20 Mar 2024

Contributed by Lukas

I’ve been working in corporate America for 23 years and I’m burnt out. Can I retire ASAP? Have a money question? Email us here Subscribe to Jill o...

Handling Money After the Loss of a Spouse

19 Mar 2024

Contributed by Lukas

My husband recently passed away and left me a large inheritance, however, I feel that my funds are scattered all over the place. How do I clean things...

How to Invest a Lump Sum

18 Mar 2024

Contributed by Lukas

With over $500k sitting in cash, how should we get it invested? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jillonm...

Ed Slott Tax Tips Part Four

17 Mar 2024

Contributed by Lukas

Tax season tips and planning with the one and only Ed Slott, the ultimate tax guru and founder of IRA Help. This is part four of four. Have a money qu...

Ed Slott Tax Tips Part Three

16 Mar 2024

Contributed by Lukas

Tax season tips and planning with the one and only Ed Slott, the ultimate tax guru and founder of IRA Help. This is part three of four. Have a money q...

Should I Switch From Roth to Pre-Tax?

15 Mar 2024

Contributed by Lukas

We're both currently maxing out our Roth 401(k)s but are considering a move for me only from a Roth to a traditional 401(k). What do you think? Have a...

Should I Do a Roth Conversion?

14 Mar 2024

Contributed by Lukas

If I don't have cash to pay the taxes on a Roth conversion, is it wise to use money in a brokerage account to pay the tax bill? Have a money question?...

How to Deal with Uncertainty

13 Mar 2024

Contributed by Lukas

My husband keeps saying we're fine and we don't need to worry, but I feel like we don't have enough of a long-term plan. Who's right? Have a money que...

Options for Stubborn Parents

12 Mar 2024

Contributed by Lukas

My parents have a tax deferred annuity that is coming due in April. They're attracted to the product as they are deferring taxes. How should they proc...

Inheritance and Retirement Planning

11 Mar 2024

Contributed by Lukas

I am 39, single, no kids, never married. I am set to inherit a little over $175,000. How should I put it to work? Have a money question? Email us here...

Ed Slott Tax Tips Part Two

10 Mar 2024

Contributed by Lukas

Tax season tips and planning with the one and only Ed Slott, the ultimate tax guru and founder of IRA Help. This is part two of four. Have a money que...

Ed Slott Tax Tips Part One

09 Mar 2024

Contributed by Lukas

Tax season tips and planning with the one and only Ed Slott, the ultimate tax guru and founder of IRA Help. This is part one of four. Have a money que...

Social Security Scams and Credit Card Fees

08 Mar 2024

Contributed by Lukas

The Federal Trade Commission reveals that con artists swindled consumers out of $10 billion in 2023, with over $126 million lost to Social Security sc...

Too Many Funds in Brokerage Account?

07 Mar 2024

Contributed by Lukas

How many funds is too many for a brokerage account? I currently have 29 ETFs. Have a money question? Email us here Subscribe to Jill on Money LIVE You...

Am I Putting Too Much Into Retirement?

06 Mar 2024

Contributed by Lukas

Should I reduce my 401(k) contributions to the match and redirect the difference to my brokerage account? I'm worried I will have to take massive RMDs...

Retirement vs Short-Term Needs

05 Mar 2024

Contributed by Lukas

Are we saving (or have saved) too much for retirement or are things we should be doing now to prioritize short-term needs over retirement? Have a mone...

Can I Leave a Job With a Pension?

04 Mar 2024

Contributed by Lukas

I have worked for the federal government for the last 15 years and qualify for a pension that increases over time, but my dream would be to have a lot...

How to Fund College

03 Mar 2024

Contributed by Lukas

With two kids getting closer and closer to college, what's the best way for us to cover the cost? Have a money question? Email us here Subscribe to Ji...

Seeking Financial Independence

02 Mar 2024

Contributed by Lukas

As we approach our 50s, are we on track to achieve financial independence in six years? Have a money question? Email us here Subscribe to Jill on Mone...

Forget Pre-Tax Contributions?

01 Mar 2024

Contributed by Lukas

When I first started working and could contribute to a 401(k) via my employer, I was all in on pre-tax. Years later I learned that it was better to sh...

Navigating Love and Finances

29 Feb 2024

Contributed by Lukas

I joined CBS Mornings with advice for couples striving for financial harmony, such as discovering the key conversations for alignment on money matters...

In a Financial Rut

28 Feb 2024

Contributed by Lukas

As I enter my 50s, I can't help but feel like I'm in a financial rut. Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @j...

Getting Back on Track

27 Feb 2024

Contributed by Lukas

After being out of the workforce for a while, how can we get our finances back on track? Have a money question? Email us here Subscribe to Jill on Mon...

Managing Finances for Ex In-Laws

26 Feb 2024

Contributed by Lukas

I've been tasked with handling the finances for my ex in-laws. Am I taking the right steps? Have a money question? Email us here Subscribe to Jill on ...

Will I Have Enough for Retirement?

25 Feb 2024

Contributed by Lukas

Despite having a few pots of money in place for retirement, I'm concerned that I won't have enough. Have a money question? Email us here Subscribe to ...

Are We Okay With One Income Stream?

24 Feb 2024

Contributed by Lukas

With my wife getting ready to stop working, will we be okay with just one stream of income? Have a money question? Email us here Subscribe to Jill on ...

Am I Saving Too Much?

23 Feb 2024

Contributed by Lukas

Am I too obsessed when it comes to saving money for retirement? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jillonm...

Did I Make an Annuity Mistake?

22 Feb 2024

Contributed by Lukas

Did I make a mistake by purchasing a fixed index annuity for nearly $500k? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTub...

Shocking Inheritance

21 Feb 2024

Contributed by Lukas

We just inherited a house and over $650,000 in various accounts. What do we do? Have a money question? Email us here Subscribe to Jill on Money LIVE Y...

Cleaning Up My Act

20 Feb 2024

Contributed by Lukas

What do I do with an old IRA that has a mix of pre-tax and post-tax contributions? Have a money question? Email us here Subscribe to Jill on Money LIV...

Next Steps After a Loss

19 Feb 2024

Contributed by Lukas

I recently inherited money and retirement funds from my husband passing away. What are the next steps? Have a money question? Email us here Subscribe ...

Is My Retirement Plan Solid?

18 Feb 2024

Contributed by Lukas

I'm a bit of a worrier so I just want to make sure that we're on track for retirement. Have a money question? Email us here Subscribe to Jill on Money...

Am I on Track at 50?

17 Feb 2024

Contributed by Lukas

After helping my son for a while, I'm now focused on my retirement. Am I on track at 50? Have a money question? Email us here Subscribe to Jill on Mon...

Is the Calculator Correct?

16 Feb 2024

Contributed by Lukas

If we contribute only $1,200 a year, will we be able to retire at age 62? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube...

Living Paycheck to Paycheck

15 Feb 2024

Contributed by Lukas

I'm earning the most that I ever have, yet I feel like I'm still living paycheck to paycheck. What gives? Have a money question? Email us here Subscri...

Hot Inflation Report

14 Feb 2024

Contributed by Lukas

The latest CPI report showed that inflation remained stubbornly high, a setback for investors betting that the Federal Reserve could cut its benchmark...

Afraid to Spend Assets

13 Feb 2024

Contributed by Lukas

We know we're in good shape for retirement, and we have more money than we'll ever need, but the decumulation phase seems to be a major hurdle. Have a...

Am I Cash Heavy?

12 Feb 2024

Contributed by Lukas

After selling some rental properties a few years back, I feel like I'm sitting on too much cash. How should I get it invested? Have a money question? ...

Is My Retirement Strategy Okay?

11 Feb 2024

Contributed by Lukas

Now that I'm in my 50s, I'm wondering if my retirement strategy is okay. Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube:...

Can We Spend the Inheritance?

10 Feb 2024

Contributed by Lukas

With a large inheritance coming our way, is it okay if we spend some of it? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTu...

Brokerage or Pre-Tax Retirement?

09 Feb 2024

Contributed by Lukas

If I am a high earner and diligent saver, would it make more sense to contribute to an after tax brokerage account or max out a pre-tax 403(b)? Have a...

Retirement Rules of Thumb

08 Feb 2024

Contributed by Lukas

Every situation in the world of personal finance is unique and different and that's why I'm no fan of the widely used retirement rules of thumb. Have ...

Did We Do the Right Thing for Mom?

07 Feb 2024

Contributed by Lukas

Have we made the right financial decisions for mom after taking over her finances? Have a money question? Email us here Subscribe to Jill on Money LIV...

Do I Have Enough to Retire?

06 Feb 2024

Contributed by Lukas

My previous company merged with a larger organization and it's unknown if I will have a role with the new company or if I will be offered a severance ...

On Track for Retirement at 55?

05 Feb 2024

Contributed by Lukas

I chatted with you guys two years ago about early retirement at 55. Am I still on track as I inch closer and closer? Have a money question? Email us h...

Ask The Compound Part Two

04 Feb 2024

Contributed by Lukas

I joined Ask The Compound with Ben Carlson and Duncan Hill to discuss Roth strategies, optimizing your portfolio rebalances, how much you should spend...

Ask The Compound Part One

03 Feb 2024

Contributed by Lukas

I joined Ask The Compound with Ben Carlson and Duncan Hill to discuss Roth strategies, optimizing your portfolio rebalances, how much you should spend...

Tax Season Tips

02 Feb 2024

Contributed by Lukas

Tax season is officially underway. The IRS says they’re anticipating more than 146 million individual tax returns to be filed by the April 15 deadli...