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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 each week to uncover surprising insights and provide actionable information so you can make the most of your money. Have a question? Email us at jillonmoney at gmail dot com.
Hoping to Not Burst the Bubble
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.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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16:2517/10/2023
Getting My Cash to Work
With a large chunk of money sitting in cash, what’s the best way to get at least some of it invested?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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18:0716/10/2023
Retirement Cash Flow Concerns
As we consider retirement in four years, we have some concerns regarding the cash flow situation.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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16:3915/10/2023
Should I Use Roth 401(k)?
I’m currently using the pre-tax option of my 401(k) but I’m starting to second guess my decision.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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08:1314/10/2023
Retirement Tax Bomb
With a large portion of our money in pre-tax accounts, should we start using the Roth option at work?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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13:5913/10/2023
Considering Semi-Retirement
After working and working for the last 35 years, is the thought of semi-retirement a possibility?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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16:3412/10/2023
Starting a New Chapter
After some fortunate investment returns, am I in position to make a career/life pivot?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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19:1111/10/2023
Learning to Be Retired
My husband recently called it quits, and as we navigate our finances in retirement, we have a few questions.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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16:1210/10/2023
Option to Retire at 62
Am I on track to have the option to retire in three years at the age of 62?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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15:1409/10/2023
Think Faster, Talk Smarter Part Two
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 the Spot, will help you develop the life-changing ability to excel in spontaneous communication situations, from public speaking to interviewing and networking.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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09:5908/10/2023
Think Faster, Talk Smarter Part One
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 the Spot, will help you develop the life-changing ability to excel in spontaneous communication situations, from public speaking to interviewing and networking.
Have a money question? Email us here
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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13:5307/10/2023
Can We Afford Two Homes?
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 afford both?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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14:0006/10/2023
Do I Need a Long-Term Care Policy?
A financial advisor is suggesting I take $300k from my IRA and put it into a variable annuity. Do I need it?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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13:4105/10/2023
Paying Daughter's Student Loan
How do you suggest we help our daughter pay on her $115,000 Grad PLUS loan that is restarting?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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13:1404/10/2023
Prepping for Retirement in 2024
With retirement now just a few months away, my question is, do I need someone to manage my money?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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16:2303/10/2023
Conquering My Fear of Risk
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.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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22:5502/10/2023
Taming the Street Part Two
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 Trust. Diana joined us to talk about her latest book, Taming the Street: The Old Guard, the New Deal, and FDR's Fight to Regulate American Capitalism, a tale that takes readers back to a time when America’s financial landscape was a jungle ruled by the titans of vast wealth, largely unrestrained by government. Want more of Jill and Diana? Subscribe to Jill on Money LIVE to watch the full chat.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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06:5501/10/2023
Taming the Street Part One
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 Trust. Diana joined us to talk about her latest book, Taming the Street: The Old Guard, the New Deal, and FDR's Fight to Regulate American Capitalism, a tale that takes readers back to a time when America’s financial landscape was a jungle ruled by the titans of vast wealth, largely unrestrained by government. Want more of Jill and Diana? Subscribe to Jill on Money LIVE to watch the full chat.
Have a money question? Email us here
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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08:1130/09/2023
Federal Student Loan Repayments Resume
I joined CBS Mornings to talk about what borrowers need to know before federal student loan repayments start back up in October.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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10:1729/09/2023
Introducing Say More with Dr? Sheila
In the world of feelings, there are winners and losers, and somebody has to be the judge.
World-renowned, self-proclaimed couples therapist Dr? Sheila invites you to sit in on her private sessions with clients. (For legal reasons, Dr? must be said in the form of a question.)
Each week, a new couple…and a new puzzle to crack. You’ll get to hear, and benefit from, many of her famous techniques as she counsels patients on overcoming disagreements, dealing with an overstepping mother-in-law, navigating open relationships, and much more.
Sit back, relax, and enjoy the show, because the best way to feel better about yourself is to compare your problems to the problems of others.
“Say More” features guests including Kate Berlant, Paul Scheer, June Diane Raphael, Ilana Glazer, Abbi Jacobson, Maya Rudolph, Ike Barinholtz, Jessica St. Clair, Lennon Parham, Paula Pell, Janine Brito, Jason Mantzoukas, Peter Grosz, Jean Villepique, Stephnie Weir, John Lutz, Fred Armisen, Rachel Dratch, Chris Parnell and Ana Gasteyer, and stars Amy Poehler as Dr? Sheila.
Say More with Dr? Sheila premieres Thursday, September 21, 2023. Listen to and follow Say More with Dr? Sheila, an Audacy production, on the Audacy app or wherever you get your podcasts.
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04:2428/09/2023
Use Savings or Take Out Mortgage?
With a new house purchase on the horizon, should we raid our brokerage account or take out a larger mortgage?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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13:1528/09/2023
Adult 529 Plan
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 plan?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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13:1427/09/2023
House Poor After Divorce
I have recently gotten divorced and now I am house poor. How should I change things to make life a little easier?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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17:4526/09/2023
Getting Close to Retirement
With retirement on the horizon, my major concern is account consolidation and how I can manage any potential tax burden.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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16:2525/09/2023
Cybersecurity Best Practices Part Two
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 remained steadfast throughout his career: educate consumers, businesses, law enforcement officials and lawmakers about consumer privacy and identity management and protection. Want more of Jill and Adam? Subscribe to Jill on Money LIVE to watch the full chat.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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05:5024/09/2023
Cybersecurity Best Practices Part One
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 remained steadfast throughout his career: educate consumers, businesses, law enforcement officials and lawmakers about consumer privacy and identity management and protection. Want more of Jill and Adam? Subscribe to Jill on Money LIVE to watch the full chat.
Have a money question? Email us here
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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07:0323/09/2023
Fed Decision and Economic Impacts of UAW Strike
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 strike and how it it might impact the economy.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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11:0222/09/2023
Pension Lump-Sum Options
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.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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18:1621/09/2023
Overfunded 529 Plan Options
With money leftover in a 529 plan for our child, is there any way we can access the money for our own retirement?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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16:2720/09/2023
Enough Saved to Retire?
I am 62 and hoping to retire in one to three years. Do I have enough saved?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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11:4819/09/2023
Can We Pull Back on Retirement?
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 me panic.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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20:3318/09/2023
Master of Change Part Two
This weekend we're joined by Brad Stulberg, whose most recent book, Master of Change: How to Excel When Everything Is Changing – Including You, offers a new model that describes change as an ongoing cycle of order, disorder, and reorder. Yes, we return to stability, but that stability is somewhere new.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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15:2017/09/2023
Master of Change Part One
This weekend we're joined by Brad Stulberg, whose most recent book, Master of Change: How to Excel When Everything Is Changing – Including You, offers a new model that describes change as an ongoing cycle of order, disorder, and reorder. Yes, we return to stability, but that stability is somewhere new.
Have a money question? Email us here
Subscribe to Jill on Money LIVE
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Twitter: @jillonmoney
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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22:0616/09/2023
Can We Ditch Our Insurance?
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?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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12:4815/09/2023
Divorce and Financial Reset
I'm recently divorced and would love some guidance on my financial future now that things have changed so drastically.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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18:3814/09/2023
Life Insurance Boot Camp
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 what they need to know.
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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10:5013/09/2023
Help, I Was Just Laid Off!
I recently got the dreaded phone call that I was laid off because my role was going offshore. How should I be preparing?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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17:3312/09/2023
Gonzo Capitalism Part Two
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 his latest book, Gonzo Capitalism: How to Make Money in An Economy That Hates You, Guillebeau takes us on a fascinating tour of this brave new world where novelty is currency, and the creators are in control. Want more of Jill and Chris? Subscribe to Jill on Money LIVE to watch the full webinar.
Have a money question? Email us here
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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05:4310/09/2023
Gonzo Capitalism Part One
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 his latest book, Gonzo Capitalism: How to Make Money in An Economy That Hates You, Guillebeau takes us on a fascinating tour of this brave new world where novelty is currency, and the creators are in control. Want more of Jill and Chris? Subscribe to Jill on Money LIVE to watch the full webinar.
Have a money question? Email us here
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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07:5009/09/2023
Managing 401(k) Allocations
After recently learning that my employer offers a Roth 401(k) option, should I switch my contributions from pre-tax to Roth?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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16:0108/09/2023
Should I Attack My Student Loan?
With $12,000 left in student loan debt, should I be laser focused on paying it off?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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18:0907/09/2023
Do I Need Whole Life Insurance?
About ten years ago I purchased a whole life insurance policy, should I keep or ditch it?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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09:4006/09/2023
Frozen by Analysis Paralysis
With some extra money on hand, I’m having a hard time deciding what to do. Save it or pay down debt?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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15:3705/09/2023
How to Combine Finances
As we think about getting married, our main issue is over combining the finances. How do we proceed?
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16:4804/09/2023
Will I Be Ready to Retire When I Want?
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?
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10:1803/09/2023
Just Retired at 55, Am I Okay?
55 and just retired, but in need of some help with my portfolio allocation.
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15:0802/09/2023
Handling a Lump-Sum Payout
After receiving a lump sum from my employer as part of a separation package, how should it be invested?
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11:4101/09/2023
Can I Join My Husband in Retirement?
Can I retire and spend some time with my husband who is already retired?
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08:4331/08/2023
Can I Retire in a Year at 65?
I’m 64 and would love to retire at 65, is this a realistic goal?
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13:2329/08/2023
Planning for Early Retirement
As I approach 50, how should I be maximizing my retirement contributions to possibly retire in five years or so?
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"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
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22:5528/08/2023