Jill on Money with Jill Schlesinger
Episodes
My Planner Is Suggesting I Buy an Annuity
18 Aug 2025
Contributed by Lukas
A financial planner is suggesting I purchase an annuity as a "private pension." Is this product necessary in my situation? Have a money question? Ema...
The Wealth Ladder With Nick Maggiulli
15 Aug 2025
Contributed by Lukas
Today we're joined by Nick Maggiulli, Chief Operating Officer for Ritholtz Wealth Management LLC, to discuss his recently released b...
Annuity Decision Headache
14 Aug 2025
Contributed by Lukas
Should I absorb the annuity surrender charges and reinvest the money into my current investment, which is earning 9% compounded quarterly? Have a mon...
How to Invest Inheritance?
13 Aug 2025
Contributed by Lukas
I would feel horrible losing a large portion of a recent inheritance, so I want to be careful, but I also want to maximize its earnings potential. Wha...
Can I Continue to Coast?
12 Aug 2025
Contributed by Lukas
When it comes to finances, I generally take the path of least resistance. Do I need to take a more active role or can I continue to coast? Have a mon...
Am I on the Correct Path?
11 Aug 2025
Contributed by Lukas
I would like to get some feedback on my plan and check if I am on the right path or if I should be making some tweaks along the way. Have a money que...
Possible Health Issues, Can I Retire?
08 Aug 2025
Contributed by Lukas
I am 61 and my husband is 59. We've been discussing my retiring next year and he would retire two years later when he is 62. Is this doable? Have a m...
Can I Retire at the End of This Year?
07 Aug 2025
Contributed by Lukas
Are we in a good spot for me to step away from my job and retire (age 58) at end of the year? Have a money question? Email us ...
Husband Is Afraid to Spend
06 Aug 2025
Contributed by Lukas
My husband still worries and is afraid to spend money. What can I tell him to help him see that things are fine and we can afford to have a little fun...
Do I Need a Financial Advisor?
05 Aug 2025
Contributed by Lukas
I have met with a third financial advisor (a fiduciary) and I'm still not convinced I need a planner. What do you think? Have a money question? Email...
Need to Find Peace and Get Some Time Back
04 Aug 2025
Contributed by Lukas
What I’ve earned, I’ve put towards many other expenses and am now wanting to pause and see how I am doing. Am I on track to find peace and get som...
55 With the Itch to Retire
01 Aug 2025
Contributed by Lukas
I don't hate my job but I can see the end in sight and would like to know if I'm close to being able to retire and spend $10k per month. Have a money...
Get Out of Here and Enjoy Your Life
31 Jul 2025
Contributed by Lukas
When I look at the numbers with a life expectancy of 90, it seems like I can finally retire with a conservative withdrawal rate. Are the numbers right...
Navigating Single Life in My 50s
30 Jul 2025
Contributed by Lukas
As I navigate my single life (no children) as I enter my mid-50s, should I be considering a long-term care policy? Have a money question? Email us ...
High Earners, Still Do Roth?
29 Jul 2025
Contributed by Lukas
Should we switch all of our retirement accounts to traditional from Roth to reduce income and qualify for all the tax deduction we are eligible for? ...
Is There an Alternative to Annuities?
28 Jul 2025
Contributed by Lukas
We've started working with a financial planning firm, and part of the strategy requires the use of annuities, is this the best approach? Have a money...
60 and Planning for Retirement at 67
25 Jul 2025
Contributed by Lukas
I’m 60 years old and plan to work until 67, at which point I would like to call it quits. Am I on track to make this happen? Have a money question?...
Job Change With No 401(k)
24 Jul 2025
Contributed by Lukas
I just changed jobs and I'm not sure what to do with my 401(k) from my previous employer as the new employer does not offer a retirement plan. Have...
Federal Service Early Retirement
23 Jul 2025
Contributed by Lukas
After 34 years of working for the government I took an early retirement offer, am I good to never work again? Have a money question? Email us ...
529 Plans vs Trump Accounts
22 Jul 2025
Contributed by Lukas
With the new Trump Accounts now in the mix, is a 529 plan still the best account for college expenses? Have a money question? Email us ...
How Far Behind Am I?
21 Jul 2025
Contributed by Lukas
After having a lot of fun in my 20s and 30s, then getting serious in my 40s, how far behind am I for retirement? Have a money question? Email us ...
Need a Better Plan to Retire in Three Years
18 Jul 2025
Contributed by Lukas
I’ve interviewed CFP providers but have chickened out when it came time to sign the documents and pay a fee, but retirement is closer than ever, and...
Don’t Earn Much, Am I on Track?
17 Jul 2025
Contributed by Lukas
Given that my cost of living is very low, can I retire in a few years at 59? Have a money question? Email us ...
Any Reason Not to Buy the Annuity?
16 Jul 2025
Contributed by Lukas
I have a one time opportunity to use my 457 pre-tax deferred compensation funds to purchase an annuity offered by Washington State to former employees...
Two Academics Facing Unstable Time
15 Jul 2025
Contributed by Lukas
I could really use your help, as we've been worrying ourselves sick thinking about what our options are and where we sit financially. Have a money qu...
Worried to Death
14 Jul 2025
Contributed by Lukas
After being retired for a few years, I am terrified thinking about the future and can't help but worry that we'll lose everything we own. Have a mone...
Retirement With Intention
11 Jul 2025
Contributed by Lukas
I recently retired after working in tech for 27 years but now I'm struggling with the transition and how to think about this new phase for the next 30...
Being Fair With Inheritance
10 Jul 2025
Contributed by Lukas
My daughter is very upset with an early inheritance she received. How should I proceed? Have a money question? Email us ...
Reset After Military Career
09 Jul 2025
Contributed by Lukas
I am retiring in June of 2026 after 30 years in the Navy. There will be some kind of reset, but before I embark, are we on track for the next phase? ...
Vacillating About Retirement
08 Jul 2025
Contributed by Lukas
Can I retire at age 59, which is the very last day of this year, or should I keep going for another year or so? Have a money question? Email us ...
Active Military, Am I on Track?
07 Jul 2025
Contributed by Lukas
We're in our 30s, have about $300k saved with a nice pension on the horizon, but we don't own any real estate. Is that holding us back? Have a money ...
An American Story With Ken Langone
04 Jul 2025
Contributed by Lukas
Since it's the 4th of July, we're re-airing an interview we did with Ken Langone, the legendary financier, who helped take a bunch of companies public...
I Don’t Want to Work Until I’m 70!
03 Jul 2025
Contributed by Lukas
I'll be turning 65 in two years and would like to retire at that time, if it's financially feasible. Is it? Have a money question? Email us ...
Any Benefit to Actively Managed 401(k)?
02 Jul 2025
Contributed by Lukas
My financial advisor is recommending a company to manage my 401(k). He says this company will be managing it constantly and said studies show they inc...
Are We Okay to Build a New House?
01 Jul 2025
Contributed by Lukas
We are building a house that will be way more expensive than we thought, initially. Are we over-extending ourselves? Have a money question? Email us ...
Possible Early Retirement Readiness
30 Jun 2025
Contributed by Lukas
If my employer, a federal agency, offers an early retirement option, can I say yes and call it quits? Have a money question? Email us ...
Is the Annuity Too Good to Be True?
27 Jun 2025
Contributed by Lukas
A financial planner is suggesting an annuity to provide guaranteed income to bridge the gap between retirement and Social Security. Is it the right pr...
Hubby Hates Job, Can He Quit?
26 Jun 2025
Contributed by Lukas
My husband hates his job, and has hated it for years. Can he get a lower paying job earning about half of what he does now, but still keep us on track...
Convincing Hubby We're Okay
25 Jun 2025
Contributed by Lukas
I've been on the show before, but I'm still struggling to convince my hubby that we have enough money to retire. Can you help again? Have a money que...
Should I Collect Social Security Early?
24 Jun 2025
Contributed by Lukas
I'm 68 and was planning on waiting until 70 for Social Security, but I am concerned about the shortfall and the potential for means testing. Should I ...
Saving for Retirement vs College Funding
23 Jun 2025
Contributed by Lukas
We're looking to increase our retirement contributions and wondering what is the best choice(s) as we would also like to help our children pay for col...
Am I in Good Shape to Retire Next Year?
20 Jun 2025
Contributed by Lukas
I'm 64 and hoping to retire next fall at the age of 65. Am I on track to do it? Have a money question? Email us ...
When Can I Safely Retire?
19 Jun 2025
Contributed by Lukas
I just turned 60 and now I'm wondering if I can retire next year? Have a money question? Email us ...
On Track for Retirement in 12 Years?
18 Jun 2025
Contributed by Lukas
With two teacher pensions on the horizon, are we on track to retire in 12 years or so? Have a money question? Email us ...
What Is a Safe Withdrawal Rate?
17 Jun 2025
Contributed by Lukas
What do you consider a safe withdrawal rate for a couple retiring at the age of 65? Have a money question? Email us ...
Back to the Office After 26 Years Remote
16 Jun 2025
Contributed by Lukas
My job of 30 years, with 26 of them being remote, is now requiring in office four days a week. How long, if at all, I will need to suck it up? Have a...
Medical Condition Has Me Pondering Retirement
13 Jun 2025
Contributed by Lukas
I am about to turn 54 and over the past few years a medical condition has slowly made it harder to work and live an active lifestyle. Can I retire? H...
New Job, New Retirement Plan Options
12 Jun 2025
Contributed by Lukas
I'm 50, changing jobs, and have to choose between a pension or a 401(k). Which should I go with? Have a money question? Email us ...
Can I Buy That Dream Retirement Home?
11 Jun 2025
Contributed by Lukas
I am looking to buy my dream retirement home and I think I'm in a strong enough position overall to take the leap. Should I do it? Have a money quest...
Retired With Various Streams of Income
10 Jun 2025
Contributed by Lukas
We are a retired couple and own three rental properties that cover all our financial needs. Should we convert our IRAs and pay the taxes now, staying ...
Life Insurance With Long-Term Care Rider
09 Jun 2025
Contributed by Lukas
Our advisor is suggesting we look into life insurance with a long-term care rider. We are concerned about the cost/benefit of such a policy and are no...
How Not To Invest
06 Jun 2025
Contributed by Lukas
Today we're joined by Barry Ritholtz, co-founder, chairman, and chief investment officer of Ritholtz Wealth Management LLC, to discuss his recently re...
A Money Reset With Pension Options
05 Jun 2025
Contributed by Lukas
I am leaving my current employer of 24 years for a new company without a pension. Should I take the lump sum or monthly payments beginning as early as...
To PLOP or Not to PLOP?
04 Jun 2025
Contributed by Lukas
With a bunch of pension options on the table, which one should we choose? Have a money question? Email us ...
I’m Getting Tired and Want to Enjoy Life
03 Jun 2025
Contributed by Lukas
All my work comes from word of mouth and my phone never stops ringing. I'm starting to get tired and want to enjoy life. Do I have enough money to ret...
Worried About Portfolio Construction
02 Jun 2025
Contributed by Lukas
With a ton of money tied up in the business, I'm starting to worry about the overall construction of our portfolio. Have a money question? Email us ...
39 and Want to Retire
30 May 2025
Contributed by Lukas
Can we stop saving for retirement and basically let about $2,100,000 and our rental home values grow without contributing more? Have a money question...
Retired and Have a New Mortgage
29 May 2025
Contributed by Lukas
With a new mortgage in retirement, one that has a high interest rate, are we okay to pay it off in the next year or so? Have a money question? Email...
Retirement Soon, Are We Ready?
28 May 2025
Contributed by Lukas
I'm 51 and preparing for retirement at the end of 2026 with a large pension on the horizon. Is there anything I'm not factoring into my decision makin...
57 and Considering Retirement
27 May 2025
Contributed by Lukas
I am currently 57 years old and considering retirement in the next one to three years. Is this doable? Have a money question? Email us ...
Make Your Bed: Little Things That Can Change Your Life
26 May 2025
Contributed by Lukas
In honor of the Memorial Day holiday, we're once again re-airing an interview we did back in 2017 with retired Admiral William “Bill” McRaven. If ...
Should I Put Extra Money in a Brokerage?
23 May 2025
Contributed by Lukas
Now that my school loans are paid off, I'm wondering what to do with my extra cash flow as well as a pretty large savings account. Have a money quest...
Mortgage Payoff Dilemma
22 May 2025
Contributed by Lukas
From what I can see, I could pay off my mortgage and still be able to live easily on Social Security and a tiny pension. Should I do it? Have a money...
Should I Leave My Job for a Pension?
21 May 2025
Contributed by Lukas
Should I leave my private sector job for a similar job with the government, one that comes with a pension? Have a money question? Email us ...
Will My Mom Be Okay in Retirement?
20 May 2025
Contributed by Lukas
My mom is somewhat late on saving for retirement and I want to understand the kind of shape she’s in as she prepares for the exit ramp. Have a mone...
Can We Go On a Reduced Schedule?
19 May 2025
Contributed by Lukas
Both wife’s and my employer offers a 32-hour per week schedule with 20% reduction in pay. Can we take advantage of this without derailing our long-t...
Why Save for Retirement?
16 May 2025
Contributed by Lukas
How can I help convince my friend to save for retirement? He and his wife are both state workers and will be entitled to a pension, so they don’t se...
House Poor and Feeling Behind
15 May 2025
Contributed by Lukas
I am 41, husband is 45, we have three kids and I can't help but feel like we are behind on saving for retirement and college. Should we be worried? H...
Head vs Heart Financial Decision
14 May 2025
Contributed by Lukas
We're no longer working and our only safety net is our savings and our investments. Are we safe? Have a money question? Email us he...
Do We Have Enough for Me to Retire?
13 May 2025
Contributed by Lukas
I'm 58 years old and have a dream of retiring early, within the next year or two, or as early as possible. My husband thinks we both need to work unti...
Retiring in June, Maybe Not a Good Idea?
12 May 2025
Contributed by Lukas
I plan on retiring from my state job in about a month at the age of 65. The financial game plan seems to work on paper, but not with large margins....
Introducing: Aspire with Emma Grede
10 May 2025
Contributed by Lukas
Build the life of your dreams and learn from the world’s most successful people. Emma Grede, one of America’s richest self-made women, wants you ...
Retirement and Pension Options
09 May 2025
Contributed by Lukas
If I want my pension to carry over to my wife after I pass, the penalty would be around $12k per year. Would it be smarter to take out a life insuranc...
Am I on Track at 39 Years Old?
08 May 2025
Contributed by Lukas
I'm 39 years old and have been with my employer for 15 years and plan to retire with them. Am I on track for a retirement around age 59? Have a money...
Did I Pull the Plug Too Soon?
07 May 2025
Contributed by Lukas
Did I pull the retirement plug too early? And if so, should I get a part-time job? Have a money question? Email us here...
Rocky Markets, Time for an Annuity?
06 May 2025
Contributed by Lukas
Given the rocky markets we've seen the last few weeks, is this the ideal environment to consider the purchase of an annuity? Have a money question? E...
In Our Mid 50s, Can We Retire?
05 May 2025
Contributed by Lukas
We're in our mid 50s and ready to call it quits, can we do it? Have a money question? Email us here Subscribe to Jill on ...
Should I Use TSP to Payoff Mortgage?
02 May 2025
Contributed by Lukas
I'm 70 years old and I want to payoff my mortgage ASAP. Should I use my TSP to pay it off? Have a money question? Email us here Subscribe to ...
Should We Invest in This Climate?
01 May 2025
Contributed by Lukas
With some proceeds from a real estate transaction about to come our way, should we invest in the market or wait until things settle down? Have a money...
I’m 47, Can I Retire Next Year?
30 Apr 2025
Contributed by Lukas
I'm only 47, yet I'm burned out and looking to call it quits next year, for good. Can I do it? Have a money question? Email us here Subscribe to Jill...
Do I Need to Work Longer?
29 Apr 2025
Contributed by Lukas
After taking a lower paying job, I'm now worried that I might have to work longer than anticipated. Have a money question? Email us here Subscribe to ...
Do We Have Enough for Retirement?
28 Apr 2025
Contributed by Lukas
I think we have enough saved for retirement, but given how crazy the world is right now, I need some reassurance. Have a money question? Email us her...
Want to Retire but Have Concerns
25 Apr 2025
Contributed by Lukas
I was thinking of retiring soon, however with the current state of the stock market I am not sure now is a good time and I want to make sure we have e...
Should I Go All Roth?
24 Apr 2025
Contributed by Lukas
With a combined income of $320k, should I be making all my retirement contributions Roth? Have a money question? Email us here Subscribe to Jill on Mo...
On Track for Retirement in Seven Years?
23 Apr 2025
Contributed by Lukas
My goal is to retire in exactly seven years. Am I on track to make this happen? Have a money question? Email us here Subscribe to Jill on Money LIVE Y...
Convincing Hubby We Have Enough
22 Apr 2025
Contributed by Lukas
My husband thinks we don't have enough money to retire, I think we do. Who's right? Have a money question? Email us here Subscribe to Jill on Money LI...
Am I Okay to Retire in a Year?
21 Apr 2025
Contributed by Lukas
With a lot of retirement decisions to be made, we want to make sure we don't mess things up. Have a money question? Email us here Subscribe to Jill on...
Concerns About My Financial Advisor
18 Apr 2025
Contributed by Lukas
Due to some concerns regarding my financial advisor, should I be looking for somebody new to manage my money? Have a money question? Email us here Sub...
Good Time to Increase Roth Conversions?
17 Apr 2025
Contributed by Lukas
In thinking about what to do in this economic downturn, I was wondering whether stepping up our Roth conversions might be a smart move? Have a money q...
Anxious About Retirement Plan
16 Apr 2025
Contributed by Lukas
We've been planning on retiring later this year, but the volatility of the current political and financial arenas is making us anxious and giving us p...
Conflicted About Early Retirement Offer
15 Apr 2025
Contributed by Lukas
As a mid-to-late career federal worker, should I even consider the buyout and early retirement offer that's currently on the table? Have a money quest...
Can I Use the Rule of 55 and Retire?
14 Apr 2025
Contributed by Lukas
I don’t like my job. So, do I take the leap now, or push through for a few more years? What are the real pros and cons beyond just the numbers? Have...
Introducing: What We Spend
12 Apr 2025
Contributed by Lukas
Imagine if you could ask someone anything you wanted about their finances. On What We Spend, people from across the country and across the financial s...
How Risky Can I Be With a Career Reset?
11 Apr 2025
Contributed by Lukas
How comfortable should I be with our financial situation in order to help us determine how much time I can afford not generating income and weigh the ...
Invest or Pay Off Mortgage?
10 Apr 2025
Contributed by Lukas
Knowing that money will never be an issue for us, should we pay off the mortgage or invest in the market? Have a money question? Email us here Subscri...
Federal Worker Feeling the Heat
09 Apr 2025
Contributed by Lukas
I am a federal employee facing uncertainty about whether my job may be eliminated in the next few months, and my husband is a researcher at a universi...
Can We Self-Manage Our Money?
08 Apr 2025
Contributed by Lukas
We are not brilliant money people, but we are starting to think it might be a good idea to get on top of the situation. Can we self-manage? Have a mon...
Here to Hold Your Hands
07 Apr 2025
Contributed by Lukas
Investors are licking their wounds after a two-day brutal sell-off, triggered by President Trump’s tariffs. We’re here to hold your hands as we st...
Can We Reach Financial Independence?
04 Apr 2025
Contributed by Lukas
We're spending a lot but we are also saving a lot now that our income is much higher. Can we still reach our goal of financial independence? Have a mo...
Federal Employee Early Retirement Offer
03 Apr 2025
Contributed by Lukas
A reduction in force is coming to my agency, but I am eligible for an early retirement offer. Should I take it? Have a money question? Email us here S...