Jill on Money with Jill Schlesinger
Host Jill Schlesinger, CFP®, tackles sometimes uncomfortable and even controversial money and investing issues, without the financial jargon, to get to the heart of what’s important for anyone to know. Jill takes listener phone calls and interviews informative and entertaining guests to uncover surprising insights and provide actionable information so you can make the most of your money.
Episodes
Does My Early Retirement Plan Work?
Does my retirement plan work as is or should I be looking to buy a deferred income annuity?Have a money question? Email us here
Where to Save in 30s and 40s?
Besides maxing out our workplace retirement accounts, we are looking for some guidance on whether to focus our savings in mainly pre or post-tax accounts.Have a money question? Email us here
Investment Philosophy
How many stocks and ETFs should a person hold in a single account? Our new advisor has each of our accounts held in more than 20 different funds.Have a money question? Email us here
Can I Retire in Four Years at 60?
I am 56 and have a very stressful job that is having negative impacts on my mental and physical health. Can I retire early or reset to a less stressful job?Have a money question? Email us here
Are We Okay to Start Withdrawals?
With my husband now out of work on disability, are we okay to start pulling money from his 401(k)?Have a money question? Email us here
Risk and Reward With Ben Carlson
Today we're sharing a recent chat with Ben Carlson, author and Director of Institutional Asset Management at Ritholtz Wealth Management.Ben joined us to discuss his recently released book Risk and Reward: How to handle market volatility and build long-term wealth, a modern guide designed to give you a better grasp of the biggest risks in investing and teach you how to protect yourself against
In Our 60s and Considering Retirement
My husband and I are considering retirement and we would like guidance on whether it's financially feasible.
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Roth or Not?
With two high salaries, does it make sense to start Roth contributions now, or wait until we retire to do conversions?
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Is Early Retirement an Option for Me?
With the goal of having more control over my time, I'm considering early retirement. Do the numbers work?
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Do We Have Enough to Retire and Live Large?
My wife and I will be 55 this year, and after years and years of saving, how do I switch my mindset from saving to spending?
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Get a Financial Life With Beth Kobliner
Today we're sharing a snippet of our recent chat with Beth Kobliner, author, financial journalist, and advocate. For three decades and counting, Beth's bestseller Get a Financial Life: Personal Finance in Your Twenties and Thirties has been the leading financial guide for young people.
Want more of Jill and Beth? Subscribe to Jill on Money LIVE to watch the full chat.
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Do I Still Need Term Life Insurance?
I'm 59 and my husband is 71, do we still need term life insurance?
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Should I Be Prioritizing the Mega Backdoor Roth?
Right now, all my excess money goes into a brokerage account. Is this the right move or should I be prioritizing the mega backdoor Roth?
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AI Is Eating My Business
With AI beginning to eat away at my business, I'm starting to panic. How should I be preparing given the risk/uncertainty around my livelihood?
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Make Your Bed With Admiral William H. McRaven
It's our annual Memorial Day tradition, as we're once again re-airing an interview we did back in 2017 with retired Admiral William “Bill” McRaven. If Bill’s name sounds familiar, it’s because he presided over the 2011 Navy SEAL raid that resulted in the killing of Osama bin Laden in Pakistan.
A few years later in 2014, the four-star admiral and 37-year Navy SEAL veteran delivered the commenceme
Tired but Afraid to Retire and Spend
After running a business for many years, I'm exhausted and would like to retire, but can't come to grips with the idea of spending what I've saved.
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Lump Sum or Monthly Payment?
With retirement on the horizon after 41 years at the same company, is it better to take the monthly pension or the lump sum?
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Job Market Concerns for Young Americans
Less than half of Americans ages 15 to 34 felt like it was a good time to find a job in 2025, a new Gallup poll shows. We're discussing on the latest episode.
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Dialing in Our Retirement Plan
We are 55 and 59, have four grown kids, all launched. We started retirement savings late but have been working hard at catching up. Are we on track?
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Okay to Retire or Semi-Retire at 55?
With an early retirement offer likely, am I in good enough shape to call it quits in my mid 50s if necessary?
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Longevity Nation: Changing the Second Half of Our Lives
Today we're sharing a snippet of our recent chat with Michael Clinton, author, thought leader, and keynote speaker on the evolving personal and business effects of the New Longevity. Michael joined us to talk about his latest book, Longevity Nation: The People, Ideas, and Trends Changing the Second Half of Our Lives.
Want more of Jill and Michael? Subscribe to Jill on Money LIVE to watch the full
I’m 45, Can I Quit My Job?
Given that my job has turned toxic, I'm wondering whether I can just pull the plug and retire for my mental sanity?
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In My 60s and Feeling Concerned
Now that I'm in my 60s and no longer working full-time, I'm starting to have some concerns about our financial future.
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Are We on the Right Track at 42?
Now that we're in our 40s I'm starting to have major concerns about our financial roadmap.
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Real Estate Loan Dilemma
With a chance to refi, should I do it or should I be more focused on saving for retirement?
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Transitioning Back Into the Workforce
As I prepare to transition back into the work force with a new degree in hand, am I taking the right financial steps?
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Prepping for Retirement at 53
With retirement at the age of 53 just weeks away, are there any financial adjustments I should be looking to make?
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Realistic Next Steps for Living Life Now?
I work a far distance from my employer, but moving closer is much more expensive due to housing costs. Is it still worth considering?
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Still on Track to Retire at 55?
With some life changes over the last few years, are we still on track to retire in our 50s?
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Should I Stay or Take the New Job Offer?
Should I stay at my current job, one that comes with a pension, or make a move for a higher salary?
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Roth vs. Traditional
I'm struggling to make a decision in terms of pre-tax versus Roth. Will it matter in my situation?
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Can We Afford to Help Out Our Sons?
With retirement right around the corner, can we afford to give our two sons a good amount of financial assistance?
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Pay Off My Mortgage Quickly?
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?
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Can I Retire at 65 Instead of 67?
The original plan was to retire at 67, but now I'm wondering if I can call it quits at 65?
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Have We Saved Enough for Retirement?
With a bit of job uncertainty entering the mix, we're wondering if we have saved enough for retirement?
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Introducing Family Lore
Family Lore is a weekly narrative podcast that celebrates and investigates ancestral mystique. Each episode begins with a guest sharing a fascinating family legend, followed by a historical deep-dive to uncover the truth and meaning behind the tale. Available now: link.pscrb.fm/f0281/FLFD
Are We Ok to Be Work Optional?
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 here
Can I Help Kids With Student Loans?
With both kids graduating with significant student loan debt, can I afford to help them out?
Have a money question? Email us here
I Want to Take Social Security Early
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 person doesn't need the money. That said, I'm starting to feel like I need the money.
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Evaluating Term Life Insurance Coverage
With a military pension and early retirement on the horizon, are we adequately covered by our existing term life insurance?
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Consolidating Old 401(k) Plans
With three different 401(k) plans in the equation, is there an easy way to simplify and make my financial life easier?
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Managing the Finances for My Mother
Should I be making any adjustments as I manage the finances for my 87 year old mother?
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Planning Around Our Pensions
With two pensions in the mix, how should we be planning for our eventual retirement?
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Managing a Career Transition
With a major career transition on the horizon, how should I be preparing financially?
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Trying Not to Screw It Up
After being diligent savers for many years, we want to make sure we don't do anything to screw things up.
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What Should I Be Doing Differently?
As I get closer and closer to 60, should I be doing something different with my investments?
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Help My Parents Plan for Retirement
I'd love a second opinion to make sure my parents are on the right track to enjoy their next life adventure.
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Reset Dilemma Advice
With a large inheritance now part of the equation, is it time for me to make a major reset?
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Has My Roth Conversion Ship Sailed?
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 conversions?
Have a money question? Email us here
Should I Tap a CD or My Roth?
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 here
Concerned About Running Out of Money
I am concerned about running out of money since I am 78 and my husband is 74. Will we be okay?
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A Holistic Giving Solution for Donors and Advisors
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 DAFgiving360.
The mission of DAFgiving360 is to increase charitable giving in the U.S. by providing a tax-smart and simple giving solution of a donor-advised fund (DAF) account and related philanthropic tools and guidance that empower donors to inco
Encore Career at Age 50?
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 here
Retirement in Three Months?
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 here
10 Years Until Retirement, Can I Do It?
I want to retire at 65 and collect my Social Security at 67. Is it possible?
Have a money question? Email us here
Life Has Changed, Are We Okay?
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 here
Can I Quit My Job at 57?
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 here
Laid Off at 62, Will We Be Okay?
My husband just got laid off after 20 years at the same company. Will we be okay?
Have a money question? Email us here
Struggling to Even Think of Retirement
If we continue doing what we're doing for the next 20 years or so, are we on track to retire at 70?
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Is 67 Our Magic Number to Retire?
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 here
Balancing Retirement With Tuition
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 tuition.
Have a money question? Email us here
Welcome to Becoming You with Suzy Welch
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 early retirement aspirations.
But we all know that the "why" is often the hardest part to solve. That’s why I’m so excited to introduce you to a voice who is cutting through the noise of modern life and work: Suzy Welch.
Suzy is a three-time New York
Too Much in a Single Stock?
With over a million-dollars in a single stock, are we taking on too much risk?
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Can I Retire in 18 Months?
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 money question? Email us here
Are We on Track, or Way Off?
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 question? Email us here
Moving From Saving to Spending
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 here
Thinking About Quitting My Job
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 on his income alone. Is he right?
Have a money question? Email us here
Options After Losing Retirement Match
Now that my employer ditched the company match, is it even worth using the retirement plan?
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Is Early Retirement a Possibility?
Given our fairly low expenses, is it reasonable to “retire” once we reach three million in assets?
Have a money question? Email us here
Can We Stop Saving for College?
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? Email us here
Are We Really Ready to Retire Early?
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 here
Impact of Iran War on Economy
I joined CBS Saturday Morning to discuss how the war against Iran is impacting the overall economy.
Have a money question? Email us here
Career Transitions With the Help of AI
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 personal career transition agent, whether you're starting out, leveling up, or reinventing what’s next.
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Financially Supporting a Parent
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 question? Email us here
How to Handle My Pension Options
With various pension options to choose from, analysis paralysis is starting to set in.
Have a money question? Email us here
On Track for FINE?
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?
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Should I Convert My TSP?
With no need to tap my pre-tax retirement accounts, should I consider converting to a Roth?
Have a money question? Email us here
Do I Need to Find Another Job?
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 here
Why Not a Roth Conversion?
Under which scenario would a Roth conversion not make the most sense?
Have a money question? Email us here
Reducing Retirement Savings for a House
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 here
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