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
How to Get Rich in American History
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 stories and wild self-experiments, Joseph tests history’s best and worst financial advice to find what worked, what didn’t, and why everyday people can still get ahead, including you.Have a money question? Email us
Wrestling With Roth Conversion Decision
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 here
Handling Healthcare Expenses in Retirement
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 headache.Have a money question? Email us
Should I Consolidate Accounts?
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 here
Buying vs Renting Struggle
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 here
Stay Calm With David Booth
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 world’s first index funds in the 1970s and launched the first passively managed small company strategy in the early ’80s.David joined us to discuss his soon-to-be released book Stay Calm: Learn to Embrace Uncertainty in Inves
The Importance of Natural Disaster Insurance
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 rent.Have a money question? Email us
How Are Americans Faring in This Economy?
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, and the tough choices many families are making to balance their budgets in today's challenging economy.Have a money question? Email us
Taking Social Security Benefits Early
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 here
Are We in Good Shape or Do We Need to Shape Up?
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 here
Out of Whack Asset Allocation
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 here
Will the Renovation Derail Us?
We're looking to do a major renovation project, will it jeopardize our long-term financial outlook?Have a money question? Email us here
Retirement Plan Options at New Job
We're looking for the most tax efficient savings vehicle for retirement contributions in a new job.Have a money question? Email us here
Downsized in Paradise, Can We Retire?
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 here
International and Domestic Travel Tips
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 here
Trump Account or 529 Plan?
With the Trump Accounts now available, is the 529 plan still the best way to save for college?Have a money question? Email us here
Time to Sell the Family Home?
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 here
Relocation in Retirement
Should I consider moving in retirement to improve my tax situation?Have a money question? Email us here
Given the Options, Are We Saving in the Right Places?
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 here
Help! I’m Going to Be a Grandma
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 here
Parents Supporting Adult Children
I recently joined CBS Saturday Morning with tips for parents who financially support their adult children.Have a money question? Email us here
Tips for Retirement Planning
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 Employee Benefit Research Institute. Have a money question? Email us
How to Calculate the Monthly Spend?
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 question? Email us here
Priorities as I Prepare for Retirement
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 here
Second Guessing My Financial Decisions
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 here
Mid-Year Financial Check-In
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 here
Funding a Condo Purchase
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 here
Does My Plan Work, or Should I Be Worried?
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 question? Email us here
Physical Job, Can I Retire at 57?
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 here
Age Gap Couple With High Paying Jobs
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 here
Social Security Mailbag With Heather Schreiber
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 Schreiber. Have a money question? Email us
Finalizing My Exit Plan at 65
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 here
Would Like to Retire in Nine Months
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? Email us here
Ensuring My Wife Will Be Taken Care Of
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 here
Pension Options and Roth Conversions
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 here
Fee-Only vs. Fee-Based
With retirement on the horizon, should I be looking for a fee-only or a fee-based advisor?Have a money question? Email us here
Freedom vs Liquidity
I say pay off the mortgage, my wife says no. Can you be the judge?Have a money question? Email us here
Am I Worrying Too Much About Taxes?
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 here
Am I Ready for Retirement?
I'm officially retiring at the end of this week. Am I ready?Have a money question? Email us here
I’m Fried, Can I Retire Next Year at 55?
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 here
How to Spend What We’ve Saved?
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 here
Making the Most of an Early Inheritance
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 here
Should I Be Focusing on a Brokerage Account?
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 here
Can I Change Jobs and Still Hit My Goals?
Can I downshift my career (work less, make less) and still hit my goal of retiring by 60?Have a money question? Email us here
Burnt Out After 42 Years in Corporate America
I'm 62, and after 42 years in the workforce, I'm wondering if I can comfortably retire?Have a money question? Email us here
Help With Mom’s Asset Allocation
My mom is 75 and I'm helping her navigate her finances. Am I making the right moves?Have a money question? Email us here
Why Use Bonds?
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 the negative column. What gives?Have a money question? Email us
Can I Make a Career Change at 57?
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 question? Email us here
Can I Take My Pension and Run?
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 here
How to Fund a Renovation?
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 here
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.
Have a money question? Email us here
Roth or Not?
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 here
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?
Have a money question? Email us here
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?
Have a money question? Email us here
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.
Have a money question? Em
Do I Still Need Term Life Insurance?
I'm 59 and my husband is 71, do we still need term life insurance?
Have a money question? Email us here
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?
Have a money question? Email us here
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?
Have a money question? Email us here
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.
Have a money question? Email us here
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?
Have a money question? Email us here
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.
Have a money question? Email us here
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?
Have a money question? Email us here
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?
Have a money question? Email us here
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?
Have a money question? Email us here
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.
Have a money question? Email us here
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.
Have a money question? Email us here
Real Estate Loan Dilemma
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 here
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?
Have a money question? Email us here
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?
Have a money question? Email us here
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?
Have a money question? Email us here
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?
Have a money question? Email us here
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?
Have a money question? Email us here
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