Jill on Money with Jill Schlesinger

How to Implement Bonds?

28 Nov 2021

Contributed by Lukas

I know my portfolio needs bonds, the question is how do I get them in there? Have a money question? Email us, ask jill [at] jill on money dot com. Ple...

Long-Term Care Insurance

27 Nov 2021

Contributed by Lukas

Long-term care insurance policies are expensive and tricky. Our latest call is an example of both. Have a money question? Email us, ask jill [at] jill...

$500k in a Single Stock

26 Nov 2021

Contributed by Lukas

Some company stock I own was worth $6,000 28-years-ago, now it's worth $500,000! As we approach retirement how should we deal with this stock? Have a ...

What We're Grateful For

25 Nov 2021

Contributed by Lukas

On today's show Mark joins me and we're hitting the pause button on the money talk and instead talking about what we're grateful for this Thanksgiving...

How to Fund College?

24 Nov 2021

Contributed by Lukas

Because the focus was always on saving for retirement, we don't have anything saved for college, which is right around the corner. What are our option...

Looking to Join the FINE Movement

23 Nov 2021

Contributed by Lukas

With thoughts of transitioning to a new endeavor in a few years time, should we be beefing up our brokerage account or continue saving in our workplac...

At 67, Is My 80/20 Portfolio Too Risky?

22 Nov 2021

Contributed by Lukas

67-years-old with an 80/20 portfolio and not phased by the ups and downs of the market, can I stay or the course or do I need to peel back the risk. ...

I'm 49, Can I Retire at 53?

21 Nov 2021

Contributed by Lukas

I'm 49-years-old and looking to retire from my current full-time job in four years. Should I be looking to get a part-time gig when the time comes? Ha...

Annuity Options

20 Nov 2021

Contributed by Lukas

When an annuity is coming due you usually have some options. Figuring out which one to choose is not always so easy. Have a money question? Email us, ...

Taking a Sabbatical at 26

19 Nov 2021

Contributed by Lukas

26-years-old and already prepping to take a sabbatical. Is this pandemic related? I'm hoping we find out the answer. Have a money question? Email us, ...

Retail Sales Surge

18 Nov 2021

Contributed by Lukas

Retail sales increased by 1.7% last month, and an overall 16.3% compared to last year. I joined CBS Mornings to explain what's behind the increase and...

Can We Shift From Retirement to College Savings?

17 Nov 2021

Contributed by Lukas

Does there come a time when it's okay to transition from saving for retirement to saving for college? Have a money question? Email us, ask jill [at] j...

Derailed by the Pandemic

16 Nov 2021

Contributed by Lukas

One day you're working your dream job and the next thing you know you're out of work, all thanks to the pandemic. Now what?  Have a money question? E...

How to Help My Mother-In-Law

15 Nov 2021

Contributed by Lukas

To qualify for medicaid, my mother-in-law wants to fully sign over her brokerage account to my husband and myself. Good idea or not? Have a money ques...

27 and Seeking Flexibility Later On

14 Nov 2021

Contributed by Lukas

This is my kinda call! Just 27-years-old and already looking to take the steps to ensure financial independence down the road. Have a money question? ...

How Much Company Stock Is Too Much?

13 Nov 2021

Contributed by Lukas

I'm not against owning company stock, but I am against owning too much of it. Remember folks, company stock should only represent a small percentage o...

What to Do With Home Sale Proceeds?

12 Nov 2021

Contributed by Lukas

Thanks to a recent home sale in this hot housing market, you've basically got $500k to play with. What should you be doing with the money?  Have a mo...

Inflation and Supply Chain Shortages

11 Nov 2021

Contributed by Lukas

Inflation is at its highest level in 31 years and supply chain problems across the country could cause havoc for people's holiday plans. On CBS Mornin...

Single Parent, Am I on Track?

10 Nov 2021

Contributed by Lukas

Being a single parent makes it hard to focus on retirement, but when your time finally comes, you want to make sure you're on the right track.  Have ...

Craving Account Consolidation

09 Nov 2021

Contributed by Lukas

When it comes to your finances, I'm a believer that less really is more. Not only with the number of funds you're using, but also with the number of ...

Help, I’m Stressing Over My Finances!

08 Nov 2021

Contributed by Lukas

I get that people stress out over their finances, but often it's unnecessary, especially when there's an obvious solution to your problems. Have a mon...

Estate Planning Drama

07 Nov 2021

Contributed by Lukas

When it comes to discussing the family finances, things can quickly get ugly. One way to avoid the drama is by having a rock-solid estate plan in plac...

Is Grad School Worth It?

06 Nov 2021

Contributed by Lukas

I'm usually not the biggest cheerleader when it comes to grad school, but does there come a point when it's actually worth it? Have a money question? ...

Does the Roth Option Make Sense for Us?

05 Nov 2021

Contributed by Lukas

If you're earning a hefty salary, does it still make sense to consider the Roth 401(k) option? As you'll hear, there's no clear and obvious answer. Ha...

Should I Use My 457 or a Brokerage Account?

04 Nov 2021

Contributed by Lukas

With some extra cash flow available each month, does it make sense to use a 457 plan and pay the taxes later, or pay the taxes now and use a brokerage...

$6,000 to Kill Bullwinkle?!?!

03 Nov 2021

Contributed by Lukas

Married couple, making a good living, with zero housing expenses. Where is all the extra cash flow going each month? Good thing Mark asked the questio...

How Are We Doing Financially?

02 Nov 2021

Contributed by Lukas

We have a million bucks in retirement accounts yet we're having a hard time coming up with an emergency fund. Any suggestions? Have a money question? ...

Should I Be Using a Brokerage Account?

01 Nov 2021

Contributed by Lukas

If you don't have a huge salary, and you know you'll have a pension come retirement, should you also be using a taxable brokerage account? Have a mone...

At What Point Is My 401(k) Not Worth Using?

31 Oct 2021

Contributed by Lukas

Some retirement plans are just so bad that you're left wondering if there's a better alternative. Have a money question? Email us, ask jill [at] jill ...

Have We Saved Enough for Retirement?

30 Oct 2021

Contributed by Lukas

We were so obsessed with paying off debt that we're now wondering if our retirement savings has suffered as a result? Have a money question? Email us,...

Hubby Says No, Wife Says Yes, Who’s Right?

29 Oct 2021

Contributed by Lukas

The wife wants a second home, husband says no way. Which way is Aunt Jill leaning? Have a money question? Email us, ask jill [at] jill on money dot co...

New Home Owner, Did I Make a Mistake?

28 Oct 2021

Contributed by Lukas

I recently took the plunge and purchased my first home. Now I'm starting to wonder if it was a mistake. Was it? Have a money question? Email us, ask j...

Can I Take a Home Office Deduction?

27 Oct 2021

Contributed by Lukas

With everyone basically working from home during the pandemic, many people are looking to take the home office deduction. But not everybody qualifies....

Going From Two Incomes to One

26 Oct 2021

Contributed by Lukas

Even though we've saved a lot money, I'm feeling a bit worried as my wife prepares to leave the workforce later this year. Will we be okay? Have a mon...

Am I Saving Too Aggressively?

25 Oct 2021

Contributed by Lukas

43-years-old and saving very aggressively for retirement with everything in stocks and not feeling the urge to have any bond allocation. Is it a mista...

Shutdown: How Covid Shook the World's Economy Part Two

24 Oct 2021

Contributed by Lukas

The shocks of 2020 have been great and small, disrupting the world economy, international relations and the daily lives of virtually everyone on the p...

Shutdown: How Covid Shook the World's Economy Part One

23 Oct 2021

Contributed by Lukas

The shocks of 2020 have been great and small, disrupting the world economy, international relations and the daily lives of virtually everyone on the p...

Tackling the Child Care Crisis

22 Oct 2021

Contributed by Lukas

Yours truly and Parents Digital Content Director Julia Dennison joined CBS Mornings to talk about how the child care crisis impacts the economy. We al...

In My 50s, Am I on Track?

21 Oct 2021

Contributed by Lukas

I'm in my 50s and trying to make up ground, am I on track or is there something else I need to be doing? Have a money question? Email us, ask jill [at...

Can We Spend Some of Our Inheritance?

20 Oct 2021

Contributed by Lukas

With a large inheritance on the horizon, is it okay if we give ourselves permission to spend some of it? Have a money question? Email us, ask jill [at...

Tax Strategies in Retirement

19 Oct 2021

Contributed by Lukas

With a lot of money in tax-deferred accounts, how concerned should you be about doing Roth conversions as you head into retirement? Have a money quest...

Should We Sell the Rental Property?

18 Oct 2021

Contributed by Lukas

Our rental property is cash flow positive and worth $600k, should we sell it? Or hang on to it for the income? Have a money question? Email us, ask ji...

Trillions: How a Band of Renegades Invented the Index Fund Part Two

17 Oct 2021

Contributed by Lukas

Fifty years ago, the Manhattan Project of money management was quietly assembled in the financial industry's backwaters, unified by the heretical idea...

Trillions: How a Band of Renegades Invented the Index Fund Part One

16 Oct 2021

Contributed by Lukas

Fifty years ago, the Manhattan Project of money management was quietly assembled in the financial industry's backwaters, unified by the heretical idea...

59 and 60, Can We Retire?

15 Oct 2021

Contributed by Lukas

Here we go, the latest early retirement question. This time from a couple currently 59 and 60 and looking to call it quits in the near future and do s...

The Great Resignation

14 Oct 2021

Contributed by Lukas

A record-breaking 4.3 million workers quit their jobs in August, the highest number ever recorded. People from all across the pay spectrum resigned, s...

Can We Retire at 62?

13 Oct 2021

Contributed by Lukas

Retirement at 62 is not always a given, but when you have an amazing perk that most don't, it certainly makes things a lot more doable. Have a money q...

Recently Retired and Have Questions

12 Oct 2021

Contributed by Lukas

Just because you're officially retired doesn't mean the questions stop. Sometimes that's when the questions just begin, especially when it comes to ol...

Which Accounts to Tap in Retirement

11 Oct 2021

Contributed by Lukas

For years you've done a great job of saving for retirement and now it's time to start tapping your various accounts. Is there any rhyme or reason as t...

It Feels Like We’re Treading Water

10 Oct 2021

Contributed by Lukas

It feels like we're treading water with our personal finances. Are we, or am I just being overly dramatic? Have a money question? Email us, ask jill [...

Where Should Our Focus Be?

09 Oct 2021

Contributed by Lukas

When it comes to our savings strategy, should we be doing a little of everything or should we be focusing on one area in particular? Have a money ques...

Student Loan Forgiveness

08 Oct 2021

Contributed by Lukas

The Department of Education announced an overhaul on a student loan forgiveness program, which could help over half a million borrowers erase their de...

Drowning in Credit Card Debt (Caller Update)

07 Oct 2021

Contributed by Lukas

Earlier this year we chatted with a listener who was drowning in credit card debt. It was a call that certainly struck a nerve with the audience. Did ...

How to Allocate Extra Cash Flow?

06 Oct 2021

Contributed by Lukas

With an extra $500 each month, how should the money be allocated? Build up the emergency reserve? Pay off the car loan? Something else? Have a money q...

Prepping for the Next Phase

05 Oct 2021

Contributed by Lukas

Prepping for retirement and the next phase brings all sorts of questions, such as whether to pay for a new house with cash or take out a mortgage? Or ...

When to Save, When to Spend?

04 Oct 2021

Contributed by Lukas

Preparing for retirement can be tricky as you're juggling two very different things, saving and determining how much you can spend. Have a money quest...

The Practice of Groundedness Part Two

03 Oct 2021

Contributed by Lukas

Achievement often comes at a cost. Angst, restlessness, frayed relationships, exhaustion, and even substance abuse can be the unwanted side effects of...

The Practice of Groundedness Part One

02 Oct 2021

Contributed by Lukas

Achievement often comes at a cost. Angst, restlessness, frayed relationships, exhaustion, and even substance abuse can be the unwanted side effects of...

What Role Do Dividends Play?

01 Oct 2021

Contributed by Lukas

When running your retirement numbers, how should you factor dividends into the equation? Have a money question? Email us, ask jill [at] jill on money ...

Debt Ceiling Fallout

30 Sep 2021

Contributed by Lukas

Secretary Janet Yellen estimates that the U.S. could default on October 18 if Congress doesn't act to raise the debt ceiling. I joined CBS Mornings to...

How Can I Help My Grandmother?

29 Sep 2021

Contributed by Lukas

My 81-year-old grandmother is not in a great financial situation, is there anything more I can be doing to help her out? Have a money question? Email ...

Can My Husband Ditch His Pension?

28 Sep 2021

Contributed by Lukas

How much is a big fat guaranteed pension worth? So much that you'd be insane to walk away from it? Have a money question? Email us, ask jill [at] jill...

Can I Start a New Endeavor at 57?

27 Sep 2021

Contributed by Lukas

Here we go, yet another career change related question. Pre-COVID, we got maybe five of these all year, now it seems like we're getting five a week. H...

Machiavelli for Women Part Two

26 Sep 2021

Contributed by Lukas

This weekend we welcome Stacey Vanek Smith, NPR host of The Indicator and correspondent for Planet Money, who joined us to discuss her recently releas...

Machiavelli for Women Part One

25 Sep 2021

Contributed by Lukas

This weekend we welcome Stacey Vanek Smith, NPR host of The Indicator and correspondent for Planet Money, who joined us to discuss her recently releas...

Is Our Portfolio Too Conservative?

24 Sep 2021

Contributed by Lukas

Even though we're retired, is our portfolio too conservative? Are we missing out on returns? Should we be taking more risk? Have a money question? Ema...

My Gap Year

23 Sep 2021

Contributed by Lukas

The pandemic has caused a lot of people to reevaluate their current professional and personal situations, and our next caller is just the latest examp...

Stocks See Lowest Drop Since May

22 Sep 2021

Contributed by Lukas

Monday, stocks saw the biggest drop in months due to a Chinese property developer on the brink of bankruptcy. I joined CBS Mornings to discuss the imp...

Are We on Target for Retirement?

21 Sep 2021

Contributed by Lukas

Are we on track for a solid retirement? I think that has become the most popular question we receive, that and Roth related questions. Here we go with...

We’re 57, Can We Retire at 60?

20 Sep 2021

Contributed by Lukas

When I run the numbers it looks like we're in good shape, so can my wife and I call it quits in three years, retire at 60, and do some traveling?  Ha...

Thrift Savings Plan For All Part Two

19 Sep 2021

Contributed by Lukas

This weekend on the show we're joined by labor economist Teresa Ghilarducci and her new co-author, Kevin Hassett (former Trump administration CEA Chai...

Thrift Savings Plan For All Part One

18 Sep 2021

Contributed by Lukas

This weekend on the show we're joined by labor economist Teresa Ghilarducci and her new co-author, Kevin Hassett (former Trump administration CEA Chai...

Are We Paying Too Much in Fees?

17 Sep 2021

Contributed by Lukas

With fees for the do-it-yourself investor at near zero, how do you know if you're being charged too much by your advisor? Have a money question? Email...

I’m 39, Can I Semi-Retire in Eight Years?

16 Sep 2021

Contributed by Lukas

I work in a career that I despise and it's taking a toll on my mental and physical health, can I power through and semi-retire in eight years? Have a ...

Labor Market Concerns

15 Sep 2021

Contributed by Lukas

Today we're talking about the surprising August unemployment numbers and why people are still unemployed and what those searching for a job should do....

How to Invest Cash on the Sidelines?

14 Sep 2021

Contributed by Lukas

Now that a home purchase is off the table, what should you do with the cash that was set aside for the down payment? Have a money question? Email us, ...

Sell the Rental and Invest the Proceeds?

13 Sep 2021

Contributed by Lukas

With the real estate market on fire, should we sell our rental and invest the proceeds, or just stick with the rental income? Have a money question? E...

Remembering 9/11 Part Two

12 Sep 2021

Contributed by Lukas

Twenty years after Sept. 11, we're giving you a break from the money talk, and instead re-airing an interview we did back in 2017 with retired Admiral...

Remembering 9/11 Part One

11 Sep 2021

Contributed by Lukas

Twenty years after Sept. 11, we're giving you a break from the money talk, and instead re-airing an interview we did back in 2017 with retired Admiral...

Is Paying Off Mortgage Early Worth It?

10 Sep 2021

Contributed by Lukas

With an extra $900 each month, does it make sense to pay extra on the mortgage, or put the money in the market? Have a money question? Email us, ask j...

Convert Rollover IRA to Roth?

09 Sep 2021

Contributed by Lukas

Five years ago the rollover IRA was worth $55,000, now it's worth $125,000, should we still consider converting to a Roth? Have a money question? Emai...

Does Our Plan Have Any Holes?

08 Sep 2021

Contributed by Lukas

When it comes to your retirement plan and running the numbers, what are some of the red flags you should be looking out for? Have a money question? Em...

Is It Okay to Invest the Emergency Fund?

07 Sep 2021

Contributed by Lukas

I know you guys are fed up with your emergency reserves earning bupkis, but does that mean you should consider placing the money in something riskier?...

Should We Sell a Rental to Pay Off Debt?

06 Sep 2021

Contributed by Lukas

With 90k in student loan debt, does it make sense to sell a rental property and wipe the slate clean? Have a money question? Email us, ask jill [at] j...

Can We Retire in 3-4 Years?

05 Sep 2021

Contributed by Lukas

Here we go, our latest question about early retirement, this time a couple looking to call it quits in 3-4 years. Doable? Have a money question? Email...

How to Handle Inherited Annuity

04 Sep 2021

Contributed by Lukas

When you inherit a variable, non-qualified annuity, what's the best course of action? Have a money question? Email us, ask jill [at] jill on money dot...

Keep Renting or Buy a Condo?

03 Sep 2021

Contributed by Lukas

Here we go with yet another real estate question. Should we keep renting or buy a condo? Have a money question? Email us, ask jill [at] jill on money ...

How Much Is a Pension Worth?

02 Sep 2021

Contributed by Lukas

Pensions are hard to come by nowadays, and that's what makes them even more valuable under the right circumstances. Have a money question? Email us, a...

Should I Convert From Traditional to Roth?

01 Sep 2021

Contributed by Lukas

Easily the most common topic we discuss on this show is somehow Roth related. Here's the latest example. Have a money question? Email us, ask jill [at...

Buy a House or Stay Put?

31 Aug 2021

Contributed by Lukas

Should I buy a house or stay put where I am? Seems to be a frequent question over the last twelve months or so. Have a money question? Email us, ask j...

Old Retirement Plan Options

30 Aug 2021

Contributed by Lukas

Should I keep my old 401(k) with my old employer, or should I roll it into my current plan? Or something else? Have a money question? Email us, ask j...

Can I Retire a Bit Early?

29 Aug 2021

Contributed by Lukas

I will soon be turning 60, and after some hard years, both physically and emotionally, am I in a solid position to retire a bit early? Have a money qu...

Do We Need Bonds?

28 Aug 2021

Contributed by Lukas

With most of our money in stocks, our financial advisor is telling us we should also be using bonds, is she right? Have a money question? Email us, as...

Overall Financial Planning

27 Aug 2021

Contributed by Lukas

The beauty of having you guys live on the show is that the conversations often take a different turn. This latest call started off talking about old r...

Social Security Claiming Strategy

26 Aug 2021

Contributed by Lukas

When it comes to claiming your Social Security benefits, it's a pretty straightforward decision making process, at least to me. Others may disagree :)...

What to Do With Home Sale Proceeds?

25 Aug 2021

Contributed by Lukas

With some cash sitting on the sidelines from a recent real estate transaction, you have a couple options regarding the money. Which is the right choic...

Passive Versus Active Investing

24 Aug 2021

Contributed by Lukas

Ah yes, the active versus passive debate. Is there any argument to be made that active investing is better than passive? Have a money question? Email ...

How to Handle Extra Cash Flow?

23 Aug 2021

Contributed by Lukas

For quite a while it was a one income household, now all of a sudden it's a two income household, which begs the question, what should we be doing wit...

Planning After a Loss

22 Aug 2021

Contributed by Lukas

Having a plan is great, but unfortunately things go wrong, forcing many of us to adjust on the fly. Have a money question? Email us, ask jill [at] jil...

Can We Retire Early?

21 Aug 2021

Contributed by Lukas

Even though I plan on working forever, I realize a lot of you want to call it quits early. The question is whether or not you're in a financial positi...