Jill on Money with Jill Schlesinger

To Pool or Not to Pool?

24 Oct 2023

Contributed by Lukas

We would like to get a pool at some point in the near future. What do you think? Would it be a dumb idea to spend all that money? Have a money questio...

Retirement Concerns at 51

23 Oct 2023

Contributed by Lukas

As I contemplate early retirement, I feel like we have plenty of money, but I feel like I have as much anxiety over not losing this money as I did acc...

Financial Wellness Part Two

22 Oct 2023

Contributed by Lukas

This weekend we're joined by Jean Chatzky, award-winning financial journalist and CEO of HerMoney.com. Jean joined us this weekend to discuss why the ...

Financial Wellness Part One

21 Oct 2023

Contributed by Lukas

This weekend we're joined by Jean Chatzky, award-winning financial journalist and CEO of HerMoney.com. Jean joined us this weekend to discuss why the ...

What to Do With Losing Stocks?

20 Oct 2023

Contributed by Lukas

I'm sitting on two funds in my IRA that have been big losers. Should I wait for them to recover or is it time to move on? Have a money question? Email...

Whole Life Mistake

19 Oct 2023

Contributed by Lukas

I have a whole life insurance policy but I no longer think it's best for me. Would you recommend I blow out of it? Have a money question? Email us her...

What's the Best Path Forward?

18 Oct 2023

Contributed by Lukas

After saving and saving for so long, I’m trying to prepare for the decumulation phase. Have a money question? Email us here Subscribe to Jill on Mon...

Hoping to Not Burst the Bubble

17 Oct 2023

Contributed by Lukas

With no real red flags, I want to make sure everything is okay and that I’m not doing anything that will burst the bubble. Have a money question? Em...

Getting My Cash to Work

16 Oct 2023

Contributed by Lukas

With a large chunk of money sitting in cash, what’s the best way to get at least some of it invested? Have a money question? Email us here Subscribe...

Retirement Cash Flow Concerns

15 Oct 2023

Contributed by Lukas

As we consider retirement in four years, we have some concerns regarding the cash flow situation. Have a money question? Email us here Subscribe to Ji...

Should I Use Roth 401(k)?

14 Oct 2023

Contributed by Lukas

I’m currently using the pre-tax option of my 401(k) but I’m starting to second guess my decision. Have a money question? Email us here Subscribe t...

Retirement Tax Bomb

13 Oct 2023

Contributed by Lukas

With a large portion of our money in pre-tax accounts, should we start using the Roth option at work? Have a money question? Email us here Subscribe t...

Considering Semi-Retirement

12 Oct 2023

Contributed by Lukas

After working and working for the last 35 years, is the thought of semi-retirement a possibility? Have a money question? Email us here Subscribe to Ji...

Starting a New Chapter

11 Oct 2023

Contributed by Lukas

After some fortunate investment returns, am I in position to make a career/life pivot? Have a money question? Email us here Subscribe to Jill on Money...

Learning to Be Retired

10 Oct 2023

Contributed by Lukas

My husband recently called it quits, and as we navigate our finances in retirement, we have a few questions. Have a money question? Email us here Subs...

Option to Retire at 62

09 Oct 2023

Contributed by Lukas

Am I on track to have the option to retire in three years at the age of 62? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTu...

Think Faster, Talk Smarter Part Two

08 Oct 2023

Contributed by Lukas

This weekend we're joined by Matt Abrahams, whose recently released book, Think Faster, Talk Smarter: How to Speak Successfully When You're Put on t...

Think Faster, Talk Smarter Part One

07 Oct 2023

Contributed by Lukas

This weekend we're joined by Matt Abrahams, whose recently released book, Think Faster, Talk Smarter: How to Speak Successfully When You're Put on t...

Can We Afford Two Homes?

06 Oct 2023

Contributed by Lukas

My wife and I had our first child, and we realize we will soon outgrow our one bedroom condo, and we're now looking to purchase a house. Can we affor...

Do I Need a Long-Term Care Policy?

05 Oct 2023

Contributed by Lukas

A financial advisor is suggesting I take $300k from my IRA and put it into a variable annuity. Do I need it? Have a money question? Email us here Subs...

Paying Daughter's Student Loan

04 Oct 2023

Contributed by Lukas

How do you suggest we help our daughter pay on her $115,000 Grad PLUS loan that is restarting? Have a money question? Email us here Subscribe to Jill ...

Prepping for Retirement in 2024

03 Oct 2023

Contributed by Lukas

With retirement now just a few months away, my question is, do I need someone to manage my money? Have a money question? Email us here Subscribe to Ji...

Conquering My Fear of Risk

02 Oct 2023

Contributed by Lukas

With a lot of money sitting in cash, I can’t get past my fear of risk, or maybe it’s that I have very little tolerance for it. Have a money questi...

Taming the Street Part Two

01 Oct 2023

Contributed by Lukas

This weekend we're joined by award-winning journalist Diana B. Henriques, bestselling author of The Wizard of Lies: Bernie Madoff and the Death of Tr...

Taming the Street Part One

30 Sep 2023

Contributed by Lukas

This weekend we're joined by award-winning journalist Diana B. Henriques, bestselling author of The Wizard of Lies: Bernie Madoff and the Death of Tr...

Federal Student Loan Repayments Resume

29 Sep 2023

Contributed by Lukas

I joined CBS Mornings to talk about what borrowers need to know before federal student loan repayments start back up in October. Have a money question...

Use Savings or Take Out Mortgage?

28 Sep 2023

Contributed by Lukas

With a new house purchase on the horizon, should we raid our brokerage account or take out a larger mortgage? Have a money question? Email us here Sub...

Adult 529 Plan

27 Sep 2023

Contributed by Lukas

I am a working professional making good money, but I am considering getting an online MBA just to scratch my academic itch. Is it worth using a 529 pl...

House Poor After Divorce

26 Sep 2023

Contributed by Lukas

I have recently gotten divorced and now I am house poor. How should I change things to make life a little easier? Have a money question? Email us here...

Getting Close to Retirement

25 Sep 2023

Contributed by Lukas

With retirement on the horizon, my major concern is account consolidation and how I can manage any potential tax burden. Have a money question? Email ...

Cybersecurity Best Practices Part Two

24 Sep 2023

Contributed by Lukas

This weekend we're joined by Adam Levin, cybersecurity expert and host of the What the Hack podcast. Adam joined us to talk about the mission that has...

Cybersecurity Best Practices Part One

23 Sep 2023

Contributed by Lukas

This weekend we're joined by Adam Levin, cybersecurity expert and host of the What the Hack podcast. Adam joined us to talk about the mission that has...

Fed Decision and Economic Impacts of UAW Strike

22 Sep 2023

Contributed by Lukas

I joined CBS Mornings to discuss the Federal Reserve's decision to hold interest rates steady this month as well as the United Auto Workers union stri...

Pension Lump-Sum Options

21 Sep 2023

Contributed by Lukas

I have a pretty small pension fund from a former job that has offered me a lump-sum pay out for 118% of the pension value and I'm not sure what to do....

Overfunded 529 Plan Options

20 Sep 2023

Contributed by Lukas

With money leftover in a 529 plan for our child, is there any way we can access the money for our own retirement? Have a money question? Email us here...

Enough Saved to Retire?

19 Sep 2023

Contributed by Lukas

I am 62 and hoping to retire in one to three years. Do I have enough saved? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTu...

Can We Pull Back on Retirement?

18 Sep 2023

Contributed by Lukas

I think we are in an okay position to start backing off a bit but saving for retirement has always been our focus so the thought of pulling back makes...

Master of Change Part Two

17 Sep 2023

Contributed by Lukas

This weekend we're joined by Brad Stulberg, whose most recent book, Master of Change: How to Excel When Everything Is Changing – Including You, of...

Master of Change Part One

16 Sep 2023

Contributed by Lukas

This weekend we're joined by Brad Stulberg, whose most recent book, Master of Change: How to Excel When Everything Is Changing – Including You, of...

Can We Ditch Our Insurance?

15 Sep 2023

Contributed by Lukas

My husband is turning 65 and I am 63. We each have term life insurance policies. At what point can we give these policies up? Have a money question? E...

Divorce and Financial Reset

14 Sep 2023

Contributed by Lukas

I'm recently divorced and would love some guidance on my financial future now that things have changed so drastically. Have a money question? Email us...

Life Insurance Boot Camp

13 Sep 2023

Contributed by Lukas

September is Life Insurance Awareness Month and I joined CBS Mornings to review the different types of life insurance, who can be a beneficiary and wh...

Help, I Was Just Laid Off!

12 Sep 2023

Contributed by Lukas

I recently got the dreaded phone call that I was laid off because my role was going offshore. How should I be preparing? Have a money question? Email ...

Can I Do a Reset?

11 Sep 2023

Contributed by Lukas

I'm looking to do a reset after moving and being downsized to part-time at work. Is it doable? Have a money question? Email us here Subscribe to Jill ...

Gonzo Capitalism Part Two

10 Sep 2023

Contributed by Lukas

This weekend we're joined by Chris Guillebeau, New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and many others. In ...

Gonzo Capitalism Part One

09 Sep 2023

Contributed by Lukas

This weekend we're joined by Chris Guillebeau, New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and many others. In ...

Managing 401(k) Allocations

08 Sep 2023

Contributed by Lukas

After recently learning that my employer offers a Roth 401(k) option, should I switch my contributions from pre-tax to Roth? Have a money question? Em...

Should I Attack My Student Loan?

07 Sep 2023

Contributed by Lukas

With $12,000 left in student loan debt, should I be laser focused on paying it off? Have a money question? Email us here Subscribe to Jill on Money LI...

Do I Need Whole Life Insurance?

06 Sep 2023

Contributed by Lukas

About ten years ago I purchased a whole life insurance policy, should I keep or ditch it? Have a money question? Email us here Subscribe to Jill on Mo...

Frozen by Analysis Paralysis

05 Sep 2023

Contributed by Lukas

With some extra money on hand, I’m having a hard time deciding what to do. Save it or pay down debt? Have a money question? Email us here Subscribe ...

How to Combine Finances

04 Sep 2023

Contributed by Lukas

As we think about getting married, our main issue is over combining the finances. How do we proceed? Have a money question? Email us here Subscribe to...

Will I Be Ready to Retire When I Want?

03 Sep 2023

Contributed by Lukas

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? Have a money question? Email ...

Just Retired at 55, Am I Okay?

02 Sep 2023

Contributed by Lukas

55 and just retired, but in need of some help with my portfolio allocation. Have a money question? Email us here Subscribe to Jill on Money LIVE YouTu...

Handling a Lump-Sum Payout

01 Sep 2023

Contributed by Lukas

After receiving a lump sum from my employer as part of a separation package, how should it be invested? Have a money question? Email us here Subscribe...

Can I Join My Husband in Retirement?

31 Aug 2023

Contributed by Lukas

Can I retire and spend some time with my husband who is already retired? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube:...

Do I Have Enough to Retire?

30 Aug 2023

Contributed by Lukas

I’m in my early 50s, and after a recent inheritance, am I okay to retire now? Have a money question? Email us here Subscribe to Jill on Money LIVE Y...

Can I Retire in a Year at 65?

29 Aug 2023

Contributed by Lukas

I’m 64 and would love to retire at 65, is this a realistic goal? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jill...

Planning for Early Retirement

28 Aug 2023

Contributed by Lukas

As I approach 50, how should I be maximizing my retirement contributions to possibly retire in five years or so? Have a money question? Email us here ...

Roth Conversions and Pro-Rata Rule

27 Aug 2023

Contributed by Lukas

What’s the best way to make a Roth conversion as clean and seamless as possible? Have a money question? Email us here Subscribe to Jill on Money LIV...

How to Allocate Extra Cash Flow

26 Aug 2023

Contributed by Lukas

With an extra $1,500 of cash flow each month, where should it be going? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: ...

Should We Buy Whole Life Insurance?

25 Aug 2023

Contributed by Lukas

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? Have a money...

Obsessed With Being Debt Free

24 Aug 2023

Contributed by Lukas

Even though I know it’s the wrong financial move, should I still throw every available penny at my student loans? Have a money question? Email us he...

Money Reset After Divorce

23 Aug 2023

Contributed by Lukas

Thanks to a recent divorce and the death of my father, I'm in search of a money reset. Have a money question? Email us here Subscribe to Jill on Money...

Can I Retire in 20 Months?

22 Aug 2023

Contributed by Lukas

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? Have a money que...

Worried About Retirement

21 Aug 2023

Contributed by Lukas

My husband thinks we're just fine for retirement, I'm not so sure. Are we on track? Have a money question? Email us here Subscribe to Jill on Money LI...

Coaching for Leaders Part Two

20 Aug 2023

Contributed by Lukas

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 leade...

Coaching for Leaders Part One

19 Aug 2023

Contributed by Lukas

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 leade...

Why Am I Losing Money With Bonds?

18 Aug 2023

Contributed by Lukas

2022 was a rough year for bonds, and so far, 2023 isn't looking much better. Have a money question? Email us here Subscribe to Jill on Money LIVE YouT...

Are We on the Right Track?

17 Aug 2023

Contributed by Lukas

We're only in our 30s, but I want to make sure that we are actually on the right track towards retirement and not falling behind without realizing it....

Trying to Re-Retire

16 Aug 2023

Contributed by Lukas

I was an early retiree failure, and now nearly four years later, I'm at the point where I am done. Will I fail again? Have a money question? Email us ...

Inherited IRA Strategy

15 Aug 2023

Contributed by Lukas

I recently inherited a traditional IRA and I have ten years to drain it. What should I do with the distributions, invest in a brokerage account or use...

What to Do With My Mother’s Home?

14 Aug 2023

Contributed by Lukas

I've been handling all my mom's finances for over a year now, and as we prepare to move her into an assisted living facility, we're not sure what to d...

Roth Conversion Considerations

13 Aug 2023

Contributed by Lukas

I'm newly retired and considering some Roth conversions, what should I be factoring into my decision? Have a money question? Email us here Subscribe t...

Managing Extra Cash Flow

12 Aug 2023

Contributed by Lukas

With significant surplus cash flow each month, where should the funds be going? Have a money question? Email us here Subscribe to Jill on Money LIVE Y...

What’s the Point of a Brokerage Account?

11 Aug 2023

Contributed by Lukas

If I can get better returns with CDs and high interest money market funds, and my managed brokerage account is essentially holding even, why do I eve...

Do I Have Enough to Retire?

10 Aug 2023

Contributed by Lukas

I'm 65, still working, and would really like to retire by 67. Do I have enough money saved to make it happen? Have a money question? Email us here Sub...

Drowning in Credit Card Mess

09 Aug 2023

Contributed by Lukas

I have $55,000 in consumer debt, yet I have plenty of assets, including plenty of accessible cash. Should I just wipe the slate clean? Have a money qu...

Late to the Investment Game

08 Aug 2023

Contributed by Lukas

I feel like I'm late to the investment game, so what should I be doing going forward in my 40s? Have a money question? Email us here Subscribe to Jill...

Next Best Steps for Our Family

07 Aug 2023

Contributed by Lukas

As we think about building wealth, what's the best strategy for us going forward? Real estate? Brokerage account? Have a money question? Email us here...

Your Future Self Part Two

06 Aug 2023

Contributed by Lukas

We've all had the desire to travel through time and see what our lives will be like later in life. But while we want the best possible future for ours...

Your Future Self Part One

05 Aug 2023

Contributed by Lukas

We've all had the desire to travel through time and see what our lives will be like later in life. But while we want the best possible future for ours...

Did I Make a Huge Mistake?

04 Aug 2023

Contributed by Lukas

Did I make a huge mistake by buying a fixed MassMutual RetireEase annuity from Fidelity? Have a money question? Email us here Subscribe to Jill on Mon...

Can I Use the Exit Ramp Soon?

03 Aug 2023

Contributed by Lukas

We have been pretty good savers all of our working years but I'm still not sure if we're going to be okay in retirement. Have a money question? Email ...

Mid-Year Money Checkup

02 Aug 2023

Contributed by Lukas

I joined CBS Mornings to discuss how to do a mid-year money check-up, including which accounts, policies, and subscriptions to review if your goal is ...

Preparing for Decumulation

01 Aug 2023

Contributed by Lukas

I am 56, recently retired and looking for help with the decumulation phase. I have tried online calculators to see how long my money will last, but I ...

What's My Next Goal?

31 Jul 2023

Contributed by Lukas

I'm in my early 30s and feel like I've already accomplished many of my financial goals. What should I tackle next? Have a money question? Email us her...

Pre-Tax or Roth 401(k)?

30 Jul 2023

Contributed by Lukas

Which option should I use for my 401(k), pre-tax or Roth? Have a money question? Email us here Subscribe to Jill on Money LIVE YouTube: @jillonmoney I...

Where to Invest Additional Funds?

29 Jul 2023

Contributed by Lukas

With some additional funds added to the mix, where's the best place to be investing? Have a money question? Email us here Subscribe to Jill on Money L...

Too Much of a Single Stock?

28 Jul 2023

Contributed by Lukas

How much of a single stock is too much? I own 5,000 shares of one company, should I consider selling? Have a money question? Email us here Subscribe t...

Should We Buy the Mountain Home?

27 Jul 2023

Contributed by Lukas

We are a professional couple in our late 50's trying to balance our dream of having a mountain home with sequential retirements over the next one to f...

Can I Retire in Five Years at 62?

26 Jul 2023

Contributed by Lukas

When I plug my numbers into the retirement calculator, it says I'm on track to call it quits in five years at 62. Is the calculator accurate? Have a m...

Is a Tiny Home Community a Good Move?

25 Jul 2023

Contributed by Lukas

I'm considering a potential life change of downsizing to reduce my expenses, which will decrease my pressure of monthly income and allow some flexibil...

Does My Wife Have to Stop Working?

24 Jul 2023

Contributed by Lukas

We are struggling with understanding how we can have my wife continue to work as a nurse with longer hours when our children are home during the summe...

How Much Company Stock Is Enough?

23 Jul 2023

Contributed by Lukas

With a couple of different options available to me, how much company stock should I be keeping within my portfolio? Have a money question? Email us he...

Roth Conversion Strategy

22 Jul 2023

Contributed by Lukas

What should we be considering as we begin to convert our traditional IRA into a Roth before required minimum distributions begin? Have a money questio...

Should I Sell Condo to Buy a House?

21 Jul 2023

Contributed by Lukas

With a potential home purchase in my crosshairs, do I need to sell my condo to make it happen? Have a money question? Email us here Subscribe to Jill ...

What Is a Reasonable Fee?

20 Jul 2023

Contributed by Lukas

I have $1.1 million in a 403(b), $50k in mutual funds and $30k in a traditional IRA and was recently quoted a .8 percent management fee. Is this reaso...

I Think We’re Okay, Are We?

19 Jul 2023

Contributed by Lukas

Considering that we both have sizable pensions, I think we're in good shape, but would love another opinion to see if there's anything I'm missing. Ha...

On Track for Retirement?

18 Jul 2023

Contributed by Lukas

I'm 63 years old and hoping to retire in two years, am I on track to make this happen? Have a money question? Email us here Subscribe to Jill on Money...

What to Do With Settlement Money?

17 Jul 2023

Contributed by Lukas

What should we do with more than $100,000 sitting in cash from a settlement? Fund our Roth IRAs? Stick it all in our brokerage account? Have a money q...