Jill on Money with Jill Schlesinger
- Episodes
- 679
- Released
- daily
- Latest episode
- Nov 13, 2026
About the podcast
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. Have a question you want us to answer on the show? Head to Jillonmoney.com and click the "Contact Us" button.
Episodes 679
Prepping for Retirement in a Year
With retirement just over a year away, have I covered all the necessary bases?Have a money question? Email us …
Show notes
With retirement just over a year away, have I covered all the necessary bases?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
How to Put Extra Cash Flow to Work
With an increase in cash flow on the horizon, how should we be putting it to work when the time comes?Have a money question? Email us …
Show notes
With an increase in cash flow on the horizon, how should we be putting it to work when the time comes?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Financial Steps Before Starting a Family
As we start to think about starting a family, are we taking the right steps to ensure a smooth financial transition?Have a money question? Email us …
Show notes
As we start to think about starting a family, are we taking the right steps to ensure a smooth financial transition?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Is My Financial Future on Track?
With retirement not too far away, should I be making any financial tweaks over the next few years?Have a money question? Email us …
Show notes
With retirement not too far away, should I be making any financial tweaks over the next few years?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Mid-Life Financial Check-In
As I do a check-in on my finances, is there anything I should be doing differently or any adjustments that should be made?Have a money question? Email us …
Show notes
As I do a check-in on my finances, is there anything I should be doing differently or any adjustments that should be made?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Introducing What We Spend
What We Spend is back for another season of diving into the financial questions you never get to ask. In Season 2 we’ll ask a brand new set of people from across the country and the financial spectrum to open …
Show notes
What We Spend is back for another season of diving into the financial questions you never get to ask. In Season 2 we’ll ask a brand new set of people from across the country and the financial spectrum to open their wallets — and their lives — and share what they make, what they want, and, for one week, what they spend. If you want to be on What We Spend, we’d love to hear from you. Write us at: [email protected]
Available now: link.pscrb.fm/f0281/WWS_JOM
Navigating the Open Enrollment Process
The benefit selection process is upon us, and today we're discussing some tips for making the most of your open enrollment period.Have a money question? Email us …
Show notes
The benefit selection process is upon us, and today we're discussing some tips for making the most of your open enrollment period.
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Can I Retire From a Demanding Career at 55?
I'm in my late 40s and wondering if I'll be able to accomplish my goal of retiring at 55. Have a money question? Email us …
Show notes
I'm in my late 40s and wondering if I'll be able to accomplish my goal of retiring at 55.
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Will an Upcoming Move Set Us Back Financially?
Will a move from California to the Pacific Northwest set us back financially?Have a money question? Email us …
Show notes
Will a move from California to the Pacific Northwest set us back financially?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Can I Retire From My Toxic Job?
I am 53, caught up in a toxic work environment, and would like to know if I can retire early?Have a money question? Email us …
Show notes
I am 53, caught up in a toxic work environment, and would like to know if I can retire early?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
The Economics of Election Day
As Americans are facing tough financial choices right now, I joined The Middle with Jeremy Hobson to discuss how people are handling them, and how those pressures could shape the way they vote in the midterms …
Show notes
As Americans are facing tough financial choices right now, I joined The Middle with Jeremy Hobson to discuss how people are handling them, and how those pressures could shape the way they vote in the midterms.
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Why Medicare Is Quite a Shock for Many
Here's a snippet from our recent Medicare webinar with Marcia Mantell. This is just a few minutes, but there's a full hour of Marcia behind the paywall. You can purchase the individual webinar here.Have a money …
Show notes
Here's a snippet from our recent Medicare webinar with Marcia Mantell. This is just a few minutes, but there's a full hour of Marcia behind the paywall. You can purchase the individual webinar here.
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
To Roth or Not to Roth?
I am 58, looking to retire in two years, and trying to decide if doing Roth conversions is worth it or not.Have a money question? Email us …
Show notes
I am 58, looking to retire in two years, and trying to decide if doing Roth conversions is worth it or not.
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Can I Retire When I Get Booted From Tech?
If, or perhaps when, I get booted from my tech industry job, will I need to find another job or can I retire?Have a money question? Email us …
Show notes
If, or perhaps when, I get booted from my tech industry job, will I need to find another job or can I retire?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Should I Take a 10% Pay Cut for a New Job?
I was recently offered a county job which comes with a pension and other good benefits but the offer is 10% less than my current salary. Would I be making a mistake by taking this offer?Have a money question? …
Show notes
I was recently offered a county job which comes with a pension and other good benefits but the offer is 10% less than my current salary. Would I be making a mistake by taking this offer?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Scared of Losing My Money
With about $300k in various accounts, I'm worried about the market and possibly losing this money. What should I do?Have a money question? Email us …
Show notes
With about $300k in various accounts, I'm worried about the market and possibly losing this money. What should I do?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Should We Stick With Our Advisor?
We have a financial advisor who is okay, but now we're wondering if we should stick with him or make a change?Have a money question? Email us …
Show notes
We have a financial advisor who is okay, but now we're wondering if we should stick with him or make a change?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
The Alphabet Soup of Medicare
Some people believe the murkiness of health care costs and lack of transparency is designed on purpose. Do you agree?Have a money question? Email us …
Show notes
Some people believe the murkiness of health care costs and lack of transparency is designed on purpose. Do you agree?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Making Sense of Life Insurance
Nearly 47% of American households say they feel financial hardship after a primary wage earner dies, according to a recent survey, which is where life insurance comes in. Have a money question? Email us …
Show notes
Nearly 47% of American households say they feel financial hardship after a primary wage earner dies, according to a recent survey, which is where life insurance comes in.
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Financing Our Dream Home
Given that we're already retired, what's the best way to finance the purchase and construction of our dream home?Have a money question? Email us …
Show notes
Given that we're already retired, what's the best way to finance the purchase and construction of our dream home?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Giving Myself Permission to Spend at 60
With plenty saved, and fairly low expenses, I'm having a hard time giving myself permission to spend some of my money.Have a money question? Email us …
Show notes
With plenty saved, and fairly low expenses, I'm having a hard time giving myself permission to spend some of my money.
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Debt vs Investing in Pre-retirement Years
With a plan to retire in about six years, should I keep contributing to my workplace retirement plan or instead focus on some outstanding debt?Have a money question? Email us …
Show notes
With a plan to retire in about six years, should I keep contributing to my workplace retirement plan or instead focus on some outstanding debt?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Is the Retirement Readiness Meter Accurate?
I have always managed my own retirement planning, but I would appreciate a second opinion to ensure my retirement readiness assessment is accurate.Have a money question? Email us …
Show notes
I have always managed my own retirement planning, but I would appreciate a second opinion to ensure my retirement readiness assessment is accurate.
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
I’m Fried, Can I Retire in a Few Months?
I'm fried, can I quit my job in six months at the age of 65?Have a money question? Email us …
Show notes
I'm fried, can I quit my job in six months at the age of 65?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Financial Decisions Ahead of Divorce
With my divorce set to be finalized in 2027, how should I be preparing for my new financial reality?Have a money question? Email us …
Show notes
With my divorce set to be finalized in 2027, how should I be preparing for my new financial reality?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Needing Direction in Retirement
I’m retired and was the caregiver for my mom who recently passed, and now I’m not exactly sure how to move forward with my financial life. Have a money question? Email us …
Show notes
I’m retired and was the caregiver for my mom who recently passed, and now I’m not exactly sure how to move forward with my financial life.
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Paula Pant and What It Takes to Build Wealth
Today we're sharing a recent chat with Paula Pant, host of the Afford Anything podcast. Each week on her show, Paula brings in economists, investors, business leaders, authors, and researchers to dig into the …
Show notes
Today we're sharing a recent chat with Paula Pant, host of the Afford Anything podcast.
Each week on her show, Paula brings in economists, investors, business leaders, authors, and researchers to dig into the five pillars of financial freedom: financial psychology, increasing income, investing, real estate, and entrepreneurship. Deep insights rooted in economics and behavioral finance.
Should We Update the House or Sell as Is?
We are getting ready to sell a house that has not been updated for 36 plus years. Should we update/renovate or sell as is at a discount? Have a money question? Email us …
Show notes
We are getting ready to sell a house that has not been updated for 36 plus years. Should we update/renovate or sell as is at a discount?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Buying a New House in Retirement
Can we afford to buy a more expensive home in retirement? If yes, how should be pay for it? Have a money question? Email us …
Show notes
Can we afford to buy a more expensive home in retirement? If yes, how should be pay for it?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
Planning to Retire in Another Country
With plans to retire overseas, what should I be thinking about as I prepare to make the move down the road?Have a money question? Email us …
Show notes
With plans to retire overseas, what should I be thinking about as I prepare to make the move down the road?
"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com.
These are the latest 40 of 679 episodes. You’ll find older episodes in the podcast’s feed.
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