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.
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Oct 2, 2026 · 16:07
With a large inheritance coming our way in a matter of months, we're unsure of what to do with the money. Have a money question? Email us…
Oct 1, 2026 · 14:15
We are looking for your opinions as to whether our plan is financially stable to get us through the early retirement years. Have a money question? Email us…
Sep 30, 2026 · 13:38
In the right circumstances, job hopping can actually be beneficial for your career and bank account. Today we're discussing how and why. Have a money question? Email us…
Sep 29, 2026 · 14:58
We should celebrate our ability to come together, to pool our money, and build something great. If you are successful in America, it's because pervious generations paid their…
Sep 28, 2026 · 21:36
We are targeting an end of 2027 retirement date, and although we have reviewed everything carefully, we are unsure if we might have overlooked something and don't know it. Have a…
Sep 26, 2026 · 2:14
From world events to everyday decisions, economics explains it all. Platypus Economics makes it clear, useful, and actually fun. Available now: link.pscrb.fm/f0281/PE_JOM
Sep 25, 2026 · 13:29
I really don't want to manage my own money, so is the fee I'm paying my advisor worth it? Have a money question? Email us…
Sep 24, 2026 · 16:53
Although I'm pretty good with numbers and accounting, the tax stuff confuses me and makes it difficult to figure out what a good financial goal would be. Have a money question?…
Sep 23, 2026 · 23:09
With my cash reserves feeling a bit low, what's the best way to replenish them? Have a money question? Email us…
Sep 22, 2026 · 12:16
Did I make a mistake by purchasing two separate annuities in retirement? Have a money question? Email us …
Sep 21, 2026 · 19:13
We're recently married and already looking forward to retirement. When will we have enough money? Have a money question? Email us…
Sep 18, 2026 · 22:07
My husband and I are wondering what the best strategy is to pay for my doctorate tuition? Have a money question? Email us…
Sep 17, 2026 · 11:44
With school back in session, we're here with some advice on how to create strong financial foundations and habits for your kids. Have a money question? Email us…
Sep 16, 2026 · 17:57
I'm 66 and still working but starting feel bummed out at the tax bills we will face due to the large pre-tax dollars we have accumulated. Have a money question? Email us…
Sep 15, 2026 · 18:44
I was recently part of a layoff and now I'm wondering if I need to go back to work full-time or will a part-time gig be enough? Have a money question? Email us…
Sep 14, 2026 · 25:26
Our financial advisor is advising us to buy long-term care insurance but we're wondering if we'd be better off investing the money instead? Have a money question? Email us…
Sep 11, 2026 · 21:28
I am considering changing advisors but not sure what questions to ask of my current advisor regarding the large number of funds he has us in. Have a money question? Email us…
Sep 10, 2026 · 9:56
Should you let artificial intelligence manage your money? While AI might be able to help you come up with a budget, experts say there are risks. Have a money question? Email us…
Sep 9, 2026 · 21:27
With an unexpected surgery on the horizon, how should I be preparing for the worst case scenario? Have a money question? Email us…
Sep 8, 2026 · 26:57
With plenty of assets at my disposal, I still can't seem to give myself permission to spend. Have a money question? Email us…
Sep 7, 2026 · 47:31
After 34 years with Consumer Reports, Mike Quincy is calling it a career, and on this Labor Day holiday, he joins us for his final appearance as the automotive writer at CR. Have…
Sep 4, 2026 · 14:49
After recently turning 50, I'm wondering if I'm going in the right financial direction? Have a money question? Email us…
Sep 3, 2026 · 13:17
After working in non-profits for years and years, it feels like I'm always stuck in financial survival mode. Have a money question? Email us…
Sep 2, 2026 · 14:15
I'm only 51, but with a pension part of the equation, is retirement at 56 a possibility? Have a money question? Email us…
Sep 1, 2026 · 10:58
I love my job, but at the age of 68, is it time to consider a life beyond work? Have a money question? Email us…
Aug 31, 2026 · 9:44
With a big birthday on the horizon, and a nice pension at work, am I in a position to call it quits? Have a money question? Email us…
Aug 28, 2026 · 30:20
Today we're sharing a recent chat with Jean Chatzky , an award-winning personal finance journalist, AARP's personal finance ambassador, and best-selling author. Jean is also…
Aug 27, 2026 · 11:24
I purchased a financial product a while back and have been second-guessing myself ever since. Have a money question? Email us…
Aug 26, 2026 · 13:09
With private school and college tuition now part of the equation, should I be looking to make some financial adjustments? Have a money question? Email us…
Aug 25, 2026 · 9:05
After receiving a huge raise, please tell me the money moves I should be making to secure my financial future. Have a money question? Email us…
Aug 24, 2026 · 22:32
Does the annuity pitch we've received make sense given our overall financial situation? Have a money question? Email us…
Aug 21, 2026 · 42:55
Today we're sharing a recent chat with Joseph Moore, author of How to Get Rich in American History: 300 Years of Financial Advice That Worked (& Didn’t) . In richly told…
Aug 20, 2026 · 20:30
With retirement upon us, and with no kids in the picture, should we be looking to convert our hefty pre-tax accounts? Have a money question? Email us…
Aug 19, 2026 · 13:52
Some older Americans find themselves at a loss when it comes to managing healthcare expenses after retirement starts. Today we're discussing how to navigate this financial…
Aug 18, 2026 · 15:59
I recently started a new job, and with my old 401(k) still with the old employer, should I be looking to consolidate accounts? Have a money question? Email us…
Aug 17, 2026 · 17:09
I'm in a new city, still own my house in the old city, and now I'm wondering if I should try to buy another piece of real estate. Have a money question? Email us…
Aug 14, 2026 · 40:47
Today we're sharing a recent chat with David Booth , founder and Chairman of Dimensional Fund Advisors . A trailblazer in the financial world, David helped create one of the…
Aug 13, 2026 · 16:32
Last year, the cost of damage from natural disasters in the U.S. was $115 billion. Today we're discussing what you need to know about insurance for your home, whether you own or…
Aug 12, 2026 · 20:52
I recently joined Jeremy Hobson on his show, The Follow Up , to discuss how Americans are navigating rising prices, the financial pressures facing households across the country,…
Aug 11, 2026 · 12:57
Even though I don’t need Social Security benefits to meet my monthly expenses, I still took them early at 67. Did I make a mistake? Have a money question? Email us…
Aug 10, 2026 · 16:16
With two pensions in the mix, and retirement on the horizon, are we in good shape or do we need to shape up? Have a money question? Email us…
Aug 7, 2026 · 10:53
With my asset allocation out of whack, should I bite the bullet and fix it all at once, or slowly over time? Have a money question? Email us…
Aug 6, 2026 · 31:42
We're looking to do a major renovation project, will it jeopardize our long-term financial outlook? Have a money question? Email us…
Aug 5, 2026 · 18:58
We're looking for the most tax efficient savings vehicle for retirement contributions in a new job. Have a money question? Email us…
Aug 4, 2026 · 12:42
I want to retire at the end of this year, can we do this without spreading ourselves too thin, or blowing up our savings? Have a money question? Email us…
Aug 3, 2026 · 14:47
Do you need travel insurance? What about foreign currency? Maybe skip it all and do a staycation! We're discussing it all on this episode. Have a money question? Email us…
Jul 31, 2026 · 13:25
With the Trump Accounts now available, is the 529 plan still the best way to save for college? Have a money question? Email us…
Jul 30, 2026 · 19:42
With a lot of variables at play, my husband and I can't decide if we should sell our house or not. I say yes, he's not so sure. Have a money question? Email us…
Jul 29, 2026 · 15:32
Should I consider moving in retirement to improve my tax situation? Have a money question? Email us …
Jul 28, 2026 · 16:24
We’re a high-earning couple in our 50s, and with several options available to us, we would like some feedback on our saving strategy. Have a money question? Email us…
Jul 27, 2026 · 19:01
With my first grandchild on the way, I'm trying to figure out the best way to move a bit closer to the family. Have a money question? Email us…
Jul 24, 2026 · 11:30
I recently joined CBS Saturday Morning with tips for parents who financially support their adult children. Have a money question? Email us…
Jul 23, 2026 · 11:53
Working and retired Americans are much less confident in their financial ability to maintain a comfortable retirement compared to a year ago, according to a new survey from the…
Jul 22, 2026 · 21:44
I've been tempted to contact the show to do a "how am I doing" check-in, but have one thing holding me back. I'm having trouble figuring out our monthly spend. Have a money…
Jul 21, 2026 · 19:48
With three more years left in the workforce, how should I be preparing as I start to think about retirement? Have a money question? Email us…
Jul 20, 2026 · 18:33
After making some recent financial money moves, I'm starting to wonder if I made the right decision or if I made a mistake? Have a money question? Email us…
Jul 17, 2026 · 10:49
I recently joined CBS Mornings with financial tips that will help you save money, from cutting bills and streaming services to savings accounts. Have a money question? Email us…
Jul 16, 2026 · 12:08
Would it be wise to use money in one of my brokerage accounts to buy a condo in a place that aligns better with my way of life? Have a money question? Email us…
Jul 15, 2026 · 22:58
Even though my husband says we're fine, I still find myself worrying about the markets and whether or not we have enough saved to last us for the long haul. Have a money…
Jul 14, 2026 · 12:37
I'm 55, work a physically demanding job, and would like to retire in two years. Do I have enough saved to make it happen? Have a money question? Email us…
Jul 13, 2026 · 23:34
With a significant age gap between us, what steps should we be taking as we plan for two very different retirements? Have a money question? Email us…
Jul 10, 2026 · 51:02
Because our recent Social Security webinar was such a hit, and we couldn't get to all the questions, today we're doing a mailbag episode with the Social Security Queen, Heather…
Jul 9, 2026 · 20:12
My industry is tech, and we've had tons of changes lately, so at 65 I'm wondering if my exit plan is a solid one? Have a money question? Email us…
Jul 8, 2026 · 15:55
I'm currently 58, retired at 49 with a pension, returned to full-time employment at 50 and now plan to retire again in nine months. Is our plan solid? Have a money question?…
Jul 7, 2026 · 18:30
With a strong Alzheimer's history in the family, how can I ensure that my wife will be taken care of should it become necessary? Have a money question? Email us…
Jul 6, 2026 · 25:52
With two big pensions in the mix, and a big pot of pre-tax money, should Roth conversions be the priority? Have a money question? Email us…
Jul 3, 2026 · 15:14
With retirement on the horizon, should I be looking for a fee-only or a fee-based advisor? Have a money question? Email us…
Jul 2, 2026 · 14:50
I say pay off the mortgage, my wife says no. Can you be the judge? Have a money question? Email us …
Jul 1, 2026 · 16:56
We are in good shape, but I don't want to do anything stupid. Am I worrying too much about taxes? Have a money question? Email us…
Jun 30, 2026 · 15:27
I'm officially retiring at the end of this week. Am I ready? Have a money question? Email us …
Jun 29, 2026 · 19:22
My goal is to retire in 2027 at the age of 55 from my 24-year corporate career due to burn out. Can I do it? Have a money question? Email us…
Jun 26, 2026 · 16:19
Even though we have more money than we'll probably ever need, I'm still having a hard time spending down some of the accounts. Can you help?! Have a money question? Email us…
Jun 25, 2026 · 10:58
My parents have offered to give me a big chunk of cash, but I'm not sure I agree with them on how it should be used. Have a money question? Email us…
Jun 24, 2026 · 10:41
I'm only in my 30s, but with early retirement a real goal, should I be focusing on a brokerage account instead of retirement accounts? Have a money question? Email us…
Jun 23, 2026 · 15:01
Can I downshift my career (work less, make less) and still hit my goal of retiring by 60? Have a money question? Email us…
Jun 22, 2026 · 16:15
I'm 62, and after 42 years in the workforce, I'm wondering if I can comfortably retire? Have a money question? Email us…
Jun 19, 2026 · 16:13
My mom is 75 and I'm helping her navigate her finances. Am I making the right moves? Have a money question? Email us…
Jun 18, 2026 · 15:21
You always talk about bonds being part of a portfolio and I have stayed away from them the past five years but decided to add a small amount in last year and they are still in…
Jun 17, 2026 · 14:58
I work in entertainment and it's a bit unsteady at the moment, up and down, and really stressful. I want to change careers and get out of this chaos. Can I do it? Have a money…
Jun 16, 2026 · 14:01
We have saved over the past 30 years, live frugally, and I am hoping I can retire in July 2027, or possibly sooner. Have a money question? Email us…
Jun 15, 2026 · 17:47
Should I drop my retirement contribution rate to 15% and save to build a garage or should I continue to contribute 24% and finance the build? Have a money question? Email us…
Jun 12, 2026 · 19:32
Does my retirement plan work as is or should I be looking to buy a deferred income annuity? Have a money question? Email us…
Jun 11, 2026 · 21:48
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?…
Jun 10, 2026 · 11:02
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…
Jun 9, 2026 · 14:51
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…
Jun 8, 2026 · 24:02
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…
Jun 5, 2026 · 32:05
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…
Jun 4, 2026 · 20:48
My husband and I are considering retirement and we would like guidance on whether it's financially feasible. Have a money question? Email us…
Jun 3, 2026 · 14:31
With two high salaries, does it make sense to start Roth contributions now, or wait until we retire to do conversions? Have a money question? Email us…
Jun 2, 2026 · 13:43
With the goal of having more control over my time, I'm considering early retirement. Do the numbers work? Have a money question? Email us…
Jun 1, 2026 · 23:44
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? Have a money question? Email us…
May 29, 2026 · 10:11
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…
May 28, 2026 · 14:11
I'm 59 and my husband is 71, do we still need term life insurance? Have a money question? Email us …
May 27, 2026 · 21:11
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? Have a money question? Email us…
May 26, 2026 · 26:39
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? Have a money question? Email us…
May 25, 2026 · 30:38
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…
May 22, 2026 · 21:55
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. Have a money question? Email…
May 21, 2026 · 19:23
With retirement on the horizon after 41 years at the same company, is it better to take the monthly pension or the lump sum? Have a money question? Email us…
May 20, 2026 · 11:35
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. Have a money…
May 19, 2026 · 23:33
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? Have a money question? Email…
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