Jill on Money with Jill Schlesinger

Feeling Stuck as I Approach Retirement

30 Dec 2025

Contributed by Lukas

I'm approaching retirement, yet after getting burned in the past, I'm feeling stuck at 63. Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Do I Have Enough to Slow Down?

29 Dec 2025

Contributed by Lukas

Given that I'm a natural worrier, I need somebody to tell me if I have enough saved to slow down. Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠...

Taking Advantage of a Unique Year

26 Dec 2025

Contributed by Lukas

Given that I've earned very little in 2025, I’m wondering if this gives me a unique opportunity to do a Roth conversion? Have a money question? Ema...

Happy Holidays From Jill and Mark!

25 Dec 2025

Contributed by Lukas

Happy Holidays from Jill and Mark!!! Whatever it is you're doing, we hope you have a good one! Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠...

Burned Out in Tech, Can I Retire at 49?

24 Dec 2025

Contributed by Lukas

I'm only 49 but I work at a high demand tech job and would like to retire. Is this a possibility? Have a money question? Email us ⁠⁠⁠⁠⁠⁠...

Maximize Our Assets and Optimize Our Taxes

23 Dec 2025

Contributed by Lukas

We're looking for some guidance on developing a financial plan that will help us maximize our assets and optimize our taxes as we prepare for retireme...

Am I Ready to Retire at 62?

22 Dec 2025

Contributed by Lukas

I am 60 and plan to retire at 62. With a pension and a rental part of the equation, can I make it happen? Have a money question? Email us ⁠⁠⁠⁠...

Roth Conversion Strategy

19 Dec 2025

Contributed by Lukas

Should I convert my traditional IRA to a Roth by maxing out our current tax bracket, or the next bracket, prior to required minimum distributions? Ha...

If I Retire, Does Our Plan Work?

18 Dec 2025

Contributed by Lukas

If I walk away from my job at the end of June 2026, and never earn another dollar, will our long-term retirement plan be impacted? Have a money quest...

Is Retirement in 2027 a Possibility?

17 Dec 2025

Contributed by Lukas

I'm 60 years old and thinking about retirement in 2027, is it doable given my circumstances? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠...

Too Much in Pre-Tax Retirement?

16 Dec 2025

Contributed by Lukas

I've done a decent job of saving for retirement over my career, but most of my savings are in pre-tax accounts. Should I switch it up for the last cou...

Can I Retire in Two Years?

15 Dec 2025

Contributed by Lukas

I'm a widow at 61 and have twin 17 year olds heading to college next year. I would like to retire in two years, but want to make sure that I have enou...

Restarting After a Divorce

12 Dec 2025

Contributed by Lukas

I'm in the middle of a messy divorce, once the dust settles, how do I get my financial life back on track? Have a money question? Email us ⁠⁠⁠⁠...

Saving in the Wrong Places

11 Dec 2025

Contributed by Lukas

After getting burned during the financial crisis, I'm starting to worry that we're saving our money in the wrong places. Have a money question? Emai...

Roth or Pre-Tax 401(k)?

10 Dec 2025

Contributed by Lukas

Is it time for me to make the switch from a pre-tax 401(k) to a Roth 401(k)? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Seeking Financial Flexibility

09 Dec 2025

Contributed by Lukas

We're in our 50s and seeking greater financial flexibility as we start to plan for our retirement. Have a money question? Email us ⁠⁠⁠⁠⁠⁠...

Can I Retire in Just Over Two Years?

08 Dec 2025

Contributed by Lukas

Am I on track to have a bit more flexibility, or even retire, in just over two years at the age of 62? Have a money question? Email us ⁠⁠⁠⁠⁠...

Are the Numbers Too Good to Be True?

05 Dec 2025

Contributed by Lukas

After playing with a bunch of retirement calculators, and seeing really positive results, are the numbers too good to be true? Have a money question?...

Keeping All the Balls in the Air

04 Dec 2025

Contributed by Lukas

After doing my best to keep our financial house in order, is it time to enlist the help of a financial planner? Have a money question? Email us ⁠⁠...

Planning Around a Diagnosis

03 Dec 2025

Contributed by Lukas

How should we be managing our finances after learning that we'll need to care for a family member? Have a money question? Email us ⁠⁠⁠⁠⁠⁠...

Can We Cut Back on Work?

02 Dec 2025

Contributed by Lukas

With a toddler in the mix, can we afford to cut back at work and spend more time with our child? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠...

Is One Million Enough?

01 Dec 2025

Contributed by Lukas

I think we have enough money but need some help convincing my wife that we're in solid shape. Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠...

State of the Economy With Diane Swonk

28 Nov 2025

Contributed by Lukas

With the year coming to a close, and with all the uncertainty given the tariffs and the recent government shutdown, Black Friday seems like a good tim...

The Stages of Job Loss

27 Nov 2025

Contributed by Lukas

The sluggish employment landscape explains why workers are now “job hugging,” rather than job hopping. The challenge is to fight the urge to hunke...

Wife Questioning Asset Allocation

26 Nov 2025

Contributed by Lukas

Our current asset allocation is 65% equities, 7% bonds, 28% cash/CDs, etc. My wife is concerned that we are taking on too much risk given our ages. Is...

Should I Refinance to Fixed Rate?

25 Nov 2025

Contributed by Lukas

I have a 10 year ARM and I'm wondering if I should refinance or ride it out a bit longer and hope that rates continue to come down? Have a money ques...

Major Move Before Retirement

24 Nov 2025

Contributed by Lukas

I made a big move in 2023 and am considering doing it again and I need your input because I don't want to blow up our retirement plans. Have a money ...

A Simple, Tax-Smart Account for Charitable Giving

21 Nov 2025

Contributed by Lukas

With Thanksgiving around the corner, the charitable giving season is upon us and changes are afoot. Of course, most people give because they want to d...

Buckets in Retirement

20 Nov 2025

Contributed by Lukas

With hopes of calling it quits in just a few years, when should I pull money from my different "buckets" once I get into retirement? Have a money que...

How to Manage Inherited Money

19 Nov 2025

Contributed by Lukas

With a large inheritance sitting in cash, should I leave it as is and take the peace of mind it provides, or invest it? Have a money question? Email ...

Help for Mom and Me

18 Nov 2025

Contributed by Lukas

I find myself at a fork in the road, and I'm hoping you can help me choose the right financial path. Have a money question? Email us ⁠⁠⁠⁠⁠⁠...

Pension and Renovation Decisions

17 Nov 2025

Contributed by Lukas

Is it foolish if I spend $300k on a renovation project during retirement? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Retirement and College Expenses

14 Nov 2025

Contributed by Lukas

Retirement and college expenses are on a collision course, how should we handle both? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Red Flag Warning

13 Nov 2025

Contributed by Lukas

Should we run screaming from a potential financial planner or am I overreacting? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Tap TSP for Renovations?

12 Nov 2025

Contributed by Lukas

Will we blow up our financial plan if we tap the TSP to fund a renovation project? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Is Our Plan Solid?

11 Nov 2025

Contributed by Lukas

With a large inheritance sitting in CDs, should we leave the money as is or start investing it? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠...

Finding a Financial Advisor

10 Nov 2025

Contributed by Lukas

I think now is the time for a financial advisor. How do I find the right one? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Best Strategy for Flexibility

07 Nov 2025

Contributed by Lukas

With early retirement in our plans, should we switch from retirement accounts to a brokerage account? Have a money question? Email us ⁠⁠⁠⁠⁠...

Terrified of Making the Wrong Move

06 Nov 2025

Contributed by Lukas

With some bad financial decisions in our past, and a large inheritance now in the picture, we're terrified of making the wrong move. Have a money qu...

Next Financial Steps After Divorce

05 Nov 2025

Contributed by Lukas

With a recent divorce now in the rearview mirror, what's the right financial game plan to ensure that I'm still on track for a solid retirement? Have...

Can I Go Part-Time?

04 Nov 2025

Contributed by Lukas

With four rental properties providing income, and low expenses, is it okay if I transition into part-time work? Have a money question? Email us ⁠⁠...

Furloughed and New Job Search

03 Nov 2025

Contributed by Lukas

Even though my husband is currently furloughed, is it okay if I start looking for a new (lesser paying) job? Have a money question? Email us ⁠⁠⁠...

Introducing How We Made Your Mother Season 2!

01 Nov 2025

Contributed by Lukas

It’s been 20 years since How I Met Your Mother premiered, and just over 10 years since the finale. Josh Radnor, who played “Ted” for nine season...

Buy a Home or Invest Instead?

31 Oct 2025

Contributed by Lukas

Am I better off continuing to rent and investing my commission checks in the stock market or should I be looking to buy? Have a money question? Email...

Can We Retire in Five Years?

30 Oct 2025

Contributed by Lukas

We are both 52 years old and my husband is completely burned out at his corporate job. Is retirement in five years a possibility? Have a money questi...

Is a Market Crash Coming?

29 Oct 2025

Contributed by Lukas

I'm worried sick that we are on the verge of a market crash. What do you think? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Debt Pay Off Questions

28 Oct 2025

Contributed by Lukas

I'm 66 and have been retired for four years, but I still have some outstanding debt, how should I tackle? Have a money question? Email us ⁠⁠⁠⁠...

Estate Planning for My Parents

27 Oct 2025

Contributed by Lukas

I'm 40 years old and am navigating the complexities of figuring out my aging parents' estate plan. Am I taking the right steps? Have a money question...

Estate Planning Awareness

24 Oct 2025

Contributed by Lukas

To recognize National Estate Planning Awareness Week, here's a snippet from our recent webinar with Juliet Kalib and Rick Kahler. Juliet is a trusts a...

Can We Make Our Dream a Reality?

23 Oct 2025

Contributed by Lukas

With two pensions on the horizon, would it be a bad idea to severely deplete our retirement accounts to purchase our dream vacation home? Have a mone...

Should I Go for the Promotion?

22 Oct 2025

Contributed by Lukas

I’m starting to feel burnout at work, and I’m being pushed by leadership to take on even more responsibilities for a promotion. Should I do it? H...

Can We Run Off to Travel the World?

21 Oct 2025

Contributed by Lukas

I'm 52 years old and am burnt out after working in technology for 30 years. Can I quit/retire and do a bit of traveling? Have a money question? Email...

Furloughed With First Child on the Way

20 Oct 2025

Contributed by Lukas

We're both federal employees and my wife is currently furloughed and pregnant with our first child. How do we navigate this period? Have a money ques...

I’m 67, Am I Ok to Retire?

17 Oct 2025

Contributed by Lukas

If I retire at 68 in 2026, I have forecasted a monthly Social Security and pension income that will cover expenses and offer a $1,300 cushion. Do you ...

My Gut Wants to Be Free of the Mortgage

16 Oct 2025

Contributed by Lukas

My gut wants to be free of the mortgage, but I also want to make the best financial decision. Please help! I hate being in limbo! Have a money questi...

Squinting to See Light at the End of the Tunnel

15 Oct 2025

Contributed by Lukas

I don't enjoy my job, so I want to be sure I'm doing everything possible to reach the day when I can call my employer and say I'm not coming in ever a...

Is It Time for Us to Get a CFP?

14 Oct 2025

Contributed by Lukas

I’ve always done our finances, but think it might be time to hand it off to a professional, but I’m really struggling with letting go. Can you hel...

Is Our Financial Picture Too Complex?

13 Oct 2025

Contributed by Lukas

I'm feeling like we've got too many irons in the financial fire. Can we pull a couple out? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Whole Life Policy With Inheritance?

10 Oct 2025

Contributed by Lukas

My uncle overseas passed away and left me a sizable inheritance. The advisor I’ve been working with recommended a whole life insurance policy. What ...

Is Retirement in Five Years Possible?

09 Oct 2025

Contributed by Lukas

My wife and I are both in our mid 50s and we're planning for retirement in about five years, can we do it? Have a money question? Email us ⁠⁠⁠⁠...

Refinancing an ARM

08 Oct 2025

Contributed by Lukas

With my adjustable rate mortgage about to reset, should I lock in now or wait a bit longer? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Evaluating Job Options

07 Oct 2025

Contributed by Lukas

I am currently employed but am in the interview process for a new opportunity and would like to know how much more the potential new employer would ne...

Making Our Next Move

06 Oct 2025

Contributed by Lukas

In the next six years I'd like to sell my business and do something else. I'm not sure what exactly, but something different.  Have a money question...

Expanding What’s Possible With Money

03 Oct 2025

Contributed by Lukas

Today we're joined by ⁠⁠⁠Jana Davis, a financial advisor and CFP® at Abacus Wealth Partners, a purpose-driven, values-centric financial adviso...

Impacts of Government Shutdown

02 Oct 2025

Contributed by Lukas

I joined CBS Mornings to break down how the government shutdown could affect the economy and your personal finances. Have a money question? Email us ...

70 and Still Working Full-Time

01 Oct 2025

Contributed by Lukas

After only recently prioritizing my retirement, will I have enough money to last 25 years or so? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠...

You Might Also Like: What Should I Do With My Money? from Morgan Stanley

01 Oct 2025

Contributed by Lukas

Kristin, a real estate agent, is totally stressed about money, especially when she thinks about her daughters' future. She does not like talking about...

Could We Retire Now if We Had To?

30 Sep 2025

Contributed by Lukas

In the scenario that we both lost our jobs right now, would we have enough to get us through to full retirement age? Have a money question? Email us ...

New Doctor, Am I Doing Enough?

29 Sep 2025

Contributed by Lukas

I'm a relatively new doctor, and I'm finally making good money, am I doing enough to prepare for retirement? Have a money question? Email us ⁠⁠⁠...

Presenting: The C-Word

27 Sep 2025

Contributed by Lukas

With every episode, Lena Dunham and Alissa Bennett take you on a historical deep dive into the life of a woman society dismissed by calling her mad, s...

Can We Cut Back Our Savings Rate?

26 Sep 2025

Contributed by Lukas

We are looking at cutting back our savings rate to enjoy a few other things while our kids are young and in the house, including not working as much a...

Peace of Mind With Allocations Heading Into Retirement

25 Sep 2025

Contributed by Lukas

I am one year away from retirement and my husband is three years out and I want to know if we should adjust our allocations? Have a money question? E...

Should I Move to a Low Cost Brokerage Firm?

24 Sep 2025

Contributed by Lukas

Should I consider moving my accounts to a low cost brokerage like Vanguard, or at this point is it better to leave them where they are? Have a money ...

Should I Convert My Traditional IRAs to Roth?

23 Sep 2025

Contributed by Lukas

I max out my 401(k) with everything going into the Roth option. I still have some pre-tax money left in a traditional IRA, should I convert it? Have ...

Student Loan Payment Strategy

22 Sep 2025

Contributed by Lukas

Should I continue making income-driven repayments and hope that the Public Service Loan Forgiveness program isn't canceled, or should I pay off the fu...

Introducing Simpsons Declassified with Nancy Cartwright

20 Sep 2025

Contributed by Lukas

Simpsons fans —THE VAULT IS OPEN!  I’m Nancy Cartwright, the voice of Bart Simpson for 35+ years, and I’m finally taking you inside Springfiel...

Left Government for Private Sector

19 Sep 2025

Contributed by Lukas

My husband and I are still young in our careers since we've both pursued higher education but we want to make sure we are on the right track to "catch...

Retirement Planning Checkup at 65

18 Sep 2025

Contributed by Lukas

I'll soon be 65 and am looking for a retirement planning checkup as I contemplate a possible new job and/or career change for the next few years. Hav...

What to Do With School Pension?

17 Sep 2025

Contributed by Lukas

My wife is not returning to teaching this year so we're trying to figure out what to do with the money in her pension plan. Have a money question? Em...

Is the Fed Ready to Cut Rates?

16 Sep 2025

Contributed by Lukas

I joined "Face the Nation with Margaret Brennan" to preview the Federal Reserve's September meeting amid the Trump administration's push for the agenc...

Downshift or Double Down?

15 Sep 2025

Contributed by Lukas

With potential big changes on the horizon, I'm looking for a gut check on where we are and if/where we could/should go next. Have a money question? E...

Is the Fee Worth It?

12 Sep 2025

Contributed by Lukas

I belatedly looked at my quarterly statements and saw that my quarterly advisement fees are in excess of $13k. Is the fee worth what I'm getting in re...

Can I Take a Break?

11 Sep 2025

Contributed by Lukas

I just turned 39, and I know it sounds crazy, but I'm feeling burned out and want to know if I can take a break from work. Have a money question? Ema...

Brokerage Over 401(k)?

10 Sep 2025

Contributed by Lukas

I am in the Roth camp for sure, but is there ever a reason to choose a brokerage account over a pre-tax 401(k)? Have a money question? Email us ⁠⁠...

I’m 28, Can I Ever Buy a House?

09 Sep 2025

Contributed by Lukas

Given the crazy housing market, will I ever be able to afford a piece of real estate? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Do We Have Enough To Retire at My Age 59.5?

08 Sep 2025

Contributed by Lukas

My calculations tell me we're okay, but now I'm wondering if we can retire even earlier than originally planned? Have a money question? Email us ⁠⁠...

Feeling Lost, What's the Next Step?

05 Sep 2025

Contributed by Lukas

I hate feeling stupid and don't want to be the dope that is too lazy to take an interest in how my money is managed. What's our next step? Have a mon...

Income Streams in Retirement

04 Sep 2025

Contributed by Lukas

What's the best way to manage four different annuities, plus Social Security, during my retirement years? Have a money question? Email us ⁠⁠⁠⁠...

59 and Considering Retirement

03 Sep 2025

Contributed by Lukas

The calculators tell me I'm okay for retirement, are they correct? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

In-Plan Roth Conversions

02 Sep 2025

Contributed by Lukas

With Roth conversions permitted within my workplace retirement plan, what's the best way to handle the taxes? Have a money question? Email us ⁠⁠⁠...

Lump Sum or Monthly Payments?

01 Sep 2025

Contributed by Lukas

With two pension choices to choose from, which one makes the most sense given our situation? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠...

On Track as We Approach Retirement?

29 Aug 2025

Contributed by Lukas

As we approach retirement age, are the finances where they should be at this stage of our lives? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠...

Should I Ditch the Target Date Fund?

28 Aug 2025

Contributed by Lukas

Is it a good move to ditch my target date fund and instead invest a bit more aggressively? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Can We Splurge a Little Bit?

27 Aug 2025

Contributed by Lukas

How much extra money can we afford to spend on "fun" things, such as travel and hobbies? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠...

Should I Combine Accounts?

26 Aug 2025

Contributed by Lukas

When I retire next year, I'll have various retirement accounts, should I look to consolidate them? Have a money question? Email us ⁠⁠⁠⁠⁠⁠...

Evaluating Pension Options

25 Aug 2025

Contributed by Lukas

With different pension options to choose from, we're not sure which one to pick for my husband. Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠...

Can I Scale Back and Live a Bit More?

22 Aug 2025

Contributed by Lukas

Am I in a good position to scale back at work and pursue my next endeavor and live a bit more? Have a money question? Email us ⁠⁠⁠⁠⁠⁠⁠...

Retirement After 25 Years, What’s Next?

21 Aug 2025

Contributed by Lukas

I know I’ve saved (what for me) seems like a ton of money but I'm not sure how to transition to not having a steady paycheck. Have a money question...

Trying to Figure Out Our Next Steps

20 Aug 2025

Contributed by Lukas

We think we are on track with our savings and want to figure out how and when we decide to sell our house and move somewhere else. Have a money quest...

At an Inflection Point, Seeking Guidance

19 Aug 2025

Contributed by Lukas

While my job is good, lamentably, the relationship with my boss is not. My position is due for renewal later this year and I'm fairly certain it will ...