Jill on Money with Jill Schlesinger
Episodes
Longevity Nation: Changing the Second Half of Our Lives
15 May 2026
Contributed by Lukas
Today we're sharing a snippet of our recent chat with Michael Clinton, author, thought leader, and keynote speaker on the evolving personal and busine...
I’m 45, Can I Quit My Job?
14 May 2026
Contributed by Lukas
Given that my job has turned toxic, I'm wondering whether I can just pull the plug and retire for my mental sanity? Have a money question? Email us...
In My 60s and Feeling Concerned
13 May 2026
Contributed by Lukas
Now that I'm in my 60s and no longer working full-time, I'm starting to have some concerns about our financial future. Have a money question? Email ...
Are We on the Right Track at 42?
12 May 2026
Contributed by Lukas
Now that we're in our 40s I'm starting to have major concerns about our financial roadmap. Have a money question? Email us ...
Real Estate Loan Dilemma
11 May 2026
Contributed by Lukas
With a chance to refi, should I do it or should I be more focused on saving for retirement? Have a money question? Email us ...
Transitioning Back Into the Workforce
08 May 2026
Contributed by Lukas
As I prepare to transition back into the work force with a new degree in hand, am I taking the right financial steps? Have a money question? Email us...
Prepping for Retirement at 53
07 May 2026
Contributed by Lukas
With retirement at the age of 53 just weeks away, are there any financial adjustments I should be looking to make? Have a money question? Email us ...
Realistic Next Steps for Living Life Now?
06 May 2026
Contributed by Lukas
I work a far distance from my employer, but moving closer is much more expensive due to housing costs. Is it still worth considering? Have a money qu...
Still on Track to Retire at 55?
05 May 2026
Contributed by Lukas
With some life changes over the last few years, are we still on track to retire in our 50s? Have a money question? Email us ...
Should I Stay or Take the New Job Offer?
04 May 2026
Contributed by Lukas
Should I stay at my current job, one that comes with a pension, or make a move for a higher salary? Have a money question? Email us ...
Roth vs. Traditional
01 May 2026
Contributed by Lukas
I'm struggling to make a decision in terms of pre-tax versus Roth. Will it matter in my situation? Have a money question? Email us ...
Can We Afford to Help Out Our Sons?
30 Apr 2026
Contributed by Lukas
With retirement right around the corner, can we afford to give our two sons a good amount of financial assistance? Have a money question? Email us ...
Pay Off My Mortgage Quickly?
29 Apr 2026
Contributed by Lukas
I always hear you say not to make paying down the mortgage a priority, but my interest rate is 6.125%. Do I have permission? Have a money question? E...
Can I Retire at 65 Instead of 67?
28 Apr 2026
Contributed by Lukas
The original plan was to retire at 67, but now I'm wondering if I can call it quits at 65? Have a money question? Email us ...
Have We Saved Enough for Retirement?
27 Apr 2026
Contributed by Lukas
With a bit of job uncertainty entering the mix, we're wondering if we have saved enough for retirement? Have a money question? Email us ...
Introducing Family Lore
25 Apr 2026
Contributed by Lukas
Family Lore is a weekly narrative podcast that celebrates and investigates ancestral mystique. Each episode begins with a guest sharing a fascinating ...
Are We Ok to Be Work Optional?
24 Apr 2026
Contributed by Lukas
After 30 years at the same company I was recently let go. Do I need to find another job? Have a money question? Email us ...
Can I Help Kids With Student Loans?
23 Apr 2026
Contributed by Lukas
With both kids graduating with significant student loan debt, can I afford to help them out? Have a money question? Email us ...
I Want to Take Social Security Early
22 Apr 2026
Contributed by Lukas
You usually tell people to wait to take Social Security as long as they are in good health and have a long life expectancy, and I tend to agree if a p...
Evaluating Term Life Insurance Coverage
21 Apr 2026
Contributed by Lukas
With a military pension and early retirement on the horizon, are we adequately covered by our existing term life insurance? Have a money question? Em...
Consolidating Old 401(k) Plans
20 Apr 2026
Contributed by Lukas
With three different 401(k) plans in the equation, is there an easy way to simplify and make my financial life easier? Have a money question? Email u...
Managing the Finances for My Mother
17 Apr 2026
Contributed by Lukas
Should I be making any adjustments as I manage the finances for my 87 year old mother? Have a money question? Email us ...
Planning Around Our Pensions
16 Apr 2026
Contributed by Lukas
With two pensions in the mix, how should we be planning for our eventual retirement? Have a money question? Email us ...
Managing a Career Transition
15 Apr 2026
Contributed by Lukas
With a major career transition on the horizon, how should I be preparing financially? Have a money question? Email us ...
Trying Not to Screw It Up
14 Apr 2026
Contributed by Lukas
After being diligent savers for many years, we want to make sure we don't do anything to screw things up. Have a money question? Email us ...
What Should I Be Doing Differently?
13 Apr 2026
Contributed by Lukas
As I get closer and closer to 60, should I be doing something different with my investments? Have a money question? Email us ...
Help My Parents Plan for Retirement
10 Apr 2026
Contributed by Lukas
I'd love a second opinion to make sure my parents are on the right track to enjoy their next life adventure. Have a money question? Email us ...
Reset Dilemma Advice
09 Apr 2026
Contributed by Lukas
With a large inheritance now part of the equation, is it time for me to make a major reset? Have a money question? Email us ...
Has My Roth Conversion Ship Sailed?
08 Apr 2026
Contributed by Lukas
During my working life all of my savings went into a tax deferred 401(k) which is now in a rollover IRA. Is it wise to consider doing some Roth conver...
Should I Tap a CD or My Roth?
07 Apr 2026
Contributed by Lukas
I need to come up with some money for the purchase of a new car. Should I us a CD or tap my Roth IRA? Have a money question? Email us ...
Concerned About Running Out of Money
06 Apr 2026
Contributed by Lukas
I am concerned about running out of money since I am 78 and my husband is 74. Will we be okay? Have a money question? Email us ...
A Holistic Giving Solution for Donors and Advisors
03 Apr 2026
Contributed by Lukas
It's never too early in the year to discuss charitable giving, and that's what we're doing today as we're joined by Julie Sunwoo, the President of ...
Encore Career at Age 50?
02 Apr 2026
Contributed by Lukas
Knowing that I just turned 50, can I still make a career change to something that I am passionate about? Have a money question? Email us ...
Retirement in Three Months?
01 Apr 2026
Contributed by Lukas
My job is just so stressful, and with parents who died early, I really want to retire. Can I do it? Have a money question? Email us ...
10 Years Until Retirement, Can I Do It?
31 Mar 2026
Contributed by Lukas
I want to retire at 65 and collect my Social Security at 67. Is it possible? Have a money question? Email us ...
Life Has Changed, Are We Okay?
30 Mar 2026
Contributed by Lukas
With some changes within our household, I'm wondering if I'm still on track to retire in my 60s? Have a money question? Email us ...
Can I Quit My Job at 57?
27 Mar 2026
Contributed by Lukas
I'm burned out and looking for reassurance that I am in a good financial position in order to leave my job. Have a money question? Email us ...
Laid Off at 62, Will We Be Okay?
26 Mar 2026
Contributed by Lukas
My husband just got laid off after 20 years at the same company. Will we be okay? Have a money question? Email us ...
Struggling to Even Think of Retirement
25 Mar 2026
Contributed by Lukas
If we continue doing what we're doing for the next 20 years or so, are we on track to retire at 70? Have a money question? Email us ...
Is 67 Our Magic Number to Retire?
24 Mar 2026
Contributed by Lukas
With various accounts scattered between us, we're wondering if we'll be able to retire in five years when we turn 67? Have a money question? Email us...
Balancing Retirement With Tuition
23 Mar 2026
Contributed by Lukas
We adopted two children late in life, and with both now in high school, we are trying to balance saving for retirement with the upcoming college tuiti...
Welcome to Becoming You with Suzy Welch
21 Mar 2026
Contributed by Lukas
Here on Jill on Money, we spend a lot of time crunching the numbers. We talk about the "how" of your life, the 401(k), the tax strategies, and the ear...
Too Much in a Single Stock?
20 Mar 2026
Contributed by Lukas
With over a million-dollars in a single stock, are we taking on too much risk? Have a money question? Email us ...
Can I Retire in 18 Months?
19 Mar 2026
Contributed by Lukas
Knowing that my wife will continue to work, and I may even do some part-time work, can I retire from my full-time job in the near future? Have a mone...
Are We on Track, or Way Off?
18 Mar 2026
Contributed by Lukas
On the one hand I think we save a lot, but we also make a lot, so it feels like we also spend a lot! Are we on track, or way off? Have a money quest...
Moving From Saving to Spending
17 Mar 2026
Contributed by Lukas
Now that I'm fully retired, I'm having a hard time making the transition from saving to spending. Have a money question? Email us ...
Thinking About Quitting My Job
16 Mar 2026
Contributed by Lukas
I'm thinking about quitting my job without getting another job. The thought of doing this stresses me out, but my husband says that we would be fine o...
Options After Losing Retirement Match
13 Mar 2026
Contributed by Lukas
Now that my employer ditched the company match, is it even worth using the retirement plan? Have a money question? Email us ...
Is Early Retirement a Possibility?
12 Mar 2026
Contributed by Lukas
Given our fairly low expenses, is it reasonable to “retire” once we reach three million in assets? Have a money question? Email us ...
Can We Stop Saving for College?
11 Mar 2026
Contributed by Lukas
With two young kids, and with a lot of money already saved in 529 plans, is it wrong to think we can stop saving for college? Have a money question? ...
Are We Really Ready to Retire Early?
10 Mar 2026
Contributed by Lukas
My husband wants to retire in a year when he turns 55, but I don't feel comfortable with our numbers. Am I wrong? Have a money question? Email us ...
Impact of Iran War on Economy
09 Mar 2026
Contributed by Lukas
I joined CBS Saturday Morning to discuss how the war against Iran is impacting the overall economy. Have a money question? Email us ...
Career Transitions With the Help of AI
06 Mar 2026
Contributed by Lukas
From the CEO of Boxed to the artificial intelligence landscape, Chieh Huang is back on the show to discuss his latest creation, Pelgo, an AI generated...
Financially Supporting a Parent
05 Mar 2026
Contributed by Lukas
Five years ago, my mom sold her house and moved in with us, and we're covering all her expenses. Are we jeopardizing our own retirement? Have a money...
How to Handle My Pension Options
04 Mar 2026
Contributed by Lukas
With various pension options to choose from, analysis paralysis is starting to set in. Have a money question? Email us ...
On Track for FINE?
03 Mar 2026
Contributed by Lukas
As we pursue financial independence, could an annuity act as a pension and give us a floor so we feel comfortable spending a set amount? Have a money...
Should I Convert My TSP?
02 Mar 2026
Contributed by Lukas
With no need to tap my pre-tax retirement accounts, should I consider converting to a Roth? Have a money question? Email us ...
Do I Need to Find Another Job?
27 Feb 2026
Contributed by Lukas
After being laid off in 2024, I'm starting to wonder if I really need to keep looking for another job? Have a money question? Email us ...
Why Not a Roth Conversion?
26 Feb 2026
Contributed by Lukas
Under which scenario would a Roth conversion not make the most sense? Have a money question? Email us ...
Reducing Retirement Savings for a House
25 Feb 2026
Contributed by Lukas
Would it be a mistake to reduce our retirement savings in order to float the purchase of a more expensive house? Have a money question? Email us ...
Changing Investment Firms
24 Feb 2026
Contributed by Lukas
My planner of 20 plus years has struck out on his own with a large fiduciary firm and would like me to move my money to his new company. Should I? ...
Full-Time Caregiver, Will I Be Okay?
23 Feb 2026
Contributed by Lukas
I'm a full-time caregiver for my parents and now I'm starting to wonder if my own finances are okay for the long haul? Have a money question? Email u...
Planning After the Death of My Wife
20 Feb 2026
Contributed by Lukas
After the death of my wife I'm looking to make some changes with my finances. Am I making a mistake? Have a money question? Email us ...
Am I on Track for a 2028 Retirement?
19 Feb 2026
Contributed by Lukas
There is a pretty good chance I am going to be offered a voluntary early retirement at some point in the near future. Am I in good shape to call it qu...
Can We Retire Now if We Get Laid Off?
18 Feb 2026
Contributed by Lukas
If we wind up jobless next year, can we retire early and focus on our health? Have a money question? Email us ...
Are We on the Correct Path?
17 Feb 2026
Contributed by Lukas
We’re DIY investors and are really just looking for a sanity check in terms of what’s a realistic retirement timeline and nest-egg target for a ho...
Can I Quit My Job and Become an Artist?
16 Feb 2026
Contributed by Lukas
I want to quit my job and take the leap and try to write full-time, but the idea is terrifying. Should I do it? Have a money question? Email us ...
Retirement and Leaving a Legacy
13 Feb 2026
Contributed by Lukas
With two sizable pensions in the picture, can I retire and focus on leaving a legacy for my kids? Have a money question? Email us ...
Time for a Financial Reset?
12 Feb 2026
Contributed by Lukas
By letting go of my home, it opened up an entirely new career as a realtor and interior designer. Can this be my new path? Have a money question? Ema...
I Got a Late Start, Am I Okay for Retirement?
11 Feb 2026
Contributed by Lukas
I got a late start, and even though my financial advisor says I am doing fine, I am still concerned about my retirement and would like another opinion...
How to Handle Home Sale Proceeds
10 Feb 2026
Contributed by Lukas
After selling our prior house, we now have $250,000 in proceeds and want to be intentional about how we use it. Have a money question? Email us ...
Can I Move Up My Retirement Age?
09 Feb 2026
Contributed by Lukas
The plan was to retire in a few years at 67, but now I'm wondering if I can call it quits at the end of this year? Have a money question? Email us ...
Is Investing a Pipe Dream?
06 Feb 2026
Contributed by Lukas
Is there any hope for hard working, tax paying Americans who love this country but feel any investment is a pipe dream? Have a money question? Email ...
Should I Pursue a Great Money Reset?
05 Feb 2026
Contributed by Lukas
Burnout at work is bad and I think I might be ready for my “Great Money Reset” in the form of a sabbatical of some type. Can I do it? Have a mone...
Can I Retire Before Kids Are Done With College?
04 Feb 2026
Contributed by Lukas
I'm 49 and would like to retire in seven years at 56 before my kids are finished with college. Doable? Have a money question? Email us ...
Can Dad Retire Comfortably?
03 Feb 2026
Contributed by Lukas
My dad is 68 and I've been his financial helper for the last few years. He wants to retire and I'd like to make sure I'm not missing something critica...
Inherited IRA Opportunities?
02 Feb 2026
Contributed by Lukas
After receiving an inheritance in the form of an IRA and a brokerage account, I would like to use this money to change my life to better align with my...
The Way of Excellence With Brad Stulberg
30 Jan 2026
Contributed by Lukas
Today we're joined by Brad Stulberg, author of the recently released book, The Way of Excellence: A Guide to True Greatness and Deep Satisfaction in a...
To Pay Off My House or Not?
29 Jan 2026
Contributed by Lukas
I’m debating whether to pay off our mortgage. We currently owe $187kat a 5.4% interest rate on a home worth about $800k. Have a money question? E...
My Wife Has Cancer, Can We Build Her Dream Cabin?
28 Jan 2026
Contributed by Lukas
Given a bad diagnosis for my wife, can we safely build her dream cabin and retire early? Have a money question? Email us ...
Am I on Track to Retire Comfortably at Age 67?
27 Jan 2026
Contributed by Lukas
I have worked very hard to save as much as possible but I am not sure if it will be enough to maintain my current standard of living if I want to reti...
Tax Season 2026 Opens
26 Jan 2026
Contributed by Lukas
Tax filers, start your engines, tax season officially opens on January 26th and this year, there are going to be a slew of changes that could impact y...
Save for Retirement or a House?
23 Jan 2026
Contributed by Lukas
As a single guy living in a high-cost area, am I better off renting forever or am I missing something by not pushing harder to buy? Have a money ques...
Inheritance Coming Our Way
22 Jan 2026
Contributed by Lukas
I am due to receive a big chunk of money as an inheritance and I'd love to get your input on how best to use the money. Have a money question? Email ...
At What Age Would I Be Able to Retire?
21 Jan 2026
Contributed by Lukas
I live in a very expensive city and would like to remain here in retirement. Knowing this, how much longer will I need to work? Have a money question...
Can I Call It Quits and Live a Little?
20 Jan 2026
Contributed by Lukas
I badly want to take a break from a well paying career, likely with no chance of going back, yet I'm concerned about healthcare until I turn 65. Hav...
Can I Retire at 62 in 2027?
19 Jan 2026
Contributed by Lukas
Can I retire at 62 in 2027, or can I even call it quits a bit earlier and be done at the end of this year? Have a money question? Email us ...
Burned Out and Really Want to Quit
16 Jan 2026
Contributed by Lukas
I'm 62 years old and burned out after 30 years as a nurse. I want to retire in 2026 if possible. Can I? Have a money question? Email us ...
When Can I Downsize My Job?
15 Jan 2026
Contributed by Lukas
I want to stop working at my current job in the next few years and move into a second act job that is less stressful and more meaningful. Is it doable...
Can Trump Cap Credit Card Rates?
14 Jan 2026
Contributed by Lukas
President Trump says he wants to cap credit card interest rates at 10% for a year by Jan. 20. I joined CBS Mornings to break down if the president has...
Roth Conversions Leading to Early Retirement?
13 Jan 2026
Contributed by Lukas
While I’m in the 22% tax bracket, should I begin making small annual Roth conversions? Have a money question? Email us ...
Managing the Moving Parts
12 Jan 2026
Contributed by Lukas
As we head into retirement it feels like we're juggling a lot of moving parts. Is there anything we're missing? Have a money question? Email us ...
Do You Need a Registered Investment Advisor?
09 Jan 2026
Contributed by Lukas
Independent Registered Investment Advisors (RIAs) are professional independent advisory firms that provide personalized financial advice to their clie...
Roth vs Pre-Tax 401(k) Contributions
08 Jan 2026
Contributed by Lukas
My employer recently announced that they will finally be offering a Roth 401(k) option. My plan is to start making Roth contributions. How will this i...
Can I Fully Retire in 2-3 Years?
07 Jan 2026
Contributed by Lukas
Can I fully retire in two or three years or do you think I'll need to find a part-time job? Have a money question? Email us ...
Could Operation in Venezuela Impact Gas Prices?
06 Jan 2026
Contributed by Lukas
President Trump claims Venezuela's oil industry will make more money with the U.S. behind it. Venezuela is estimated to have 303 billion barrels of cr...
Pension Lump Sum or Annuity?
05 Jan 2026
Contributed by Lukas
Have I saved enough to retire now, and if so, should I take a lump sum pension from my employer or the lifetime annuity? Have a money question? Email...
The Secrets of Perfect Timing Part Two
02 Jan 2026
Contributed by Lukas
Everyone knows that timing is everything, and what better time to dissect and analyze the science behind it than the end of one year and the beginning...
The Secrets of Perfect Timing Part One
01 Jan 2026
Contributed by Lukas
Everyone knows that timing is everything, and what better time to dissect and analyze the science behind it than the end of one year and the beginning...
Should I Be Making Financial Tweaks?
31 Dec 2025
Contributed by Lukas
I'm 64 and wondering if I should be making any tweaks to my financial game plan? Have a money question? Email us ...