Synopsis
Host Jill Schlesinger, CFP®, tackles sometimes uncomfortable and even controversial money and investing issues, without the financial jargon, to get to the heart of whats 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 askjill at jillonmoney dot com.
Episodes
-
Should I Be Prioritizing the Mega Backdoor Roth?
27/05/2026 Duration: 21minRight 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 Subscribe to Jill on Money LIVE Subscribe to
-
AI Is Eating My Business
26/05/2026 Duration: 26minWith 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 Subscribe to Jill on Money LIVE Subscribe to
-
Make Your Bed With Admiral William H. McRaven
25/05/2026 Duration: 30minIt'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 commencement speech at his alma mater, the University of Texas at Austin. Little did McRaven know that his address, which spoke to how students could overcome challenges and change themselves, would become a viral hit with 20 million views online. McRaven was eventually encouraged to expand his commencement speech into a book, Make Your Bed: Little Things That Can Change Your Life…And Maybe the World. Have a money question? Email us here Subscribe to
-
Tired but Afraid to Retire and Spend
22/05/2026 Duration: 21minAfter 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 Subscribe to Jill on Money LIVE Subscribe to
-
Lump Sum or Monthly Payment?
21/05/2026 Duration: 19minWith 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 Subscribe to Jill on Money LIVE Subscribe to
-
Job Market Concerns for Young Americans
20/05/2026 Duration: 11minLess 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 Subscribe to Jill on Money LIVE Subscribe to
-
Dialing in Our Retirement Plan
19/05/2026 Duration: 23minWe 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 Subscribe to Jill on Money LIVE Subscribe to
-
Okay to Retire or Semi-Retire at 55?
18/05/2026 Duration: 20minWith 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 Subscribe to Jill on Money LIVE Subscribe to
-
Longevity Nation: Changing the Second Half of Our Lives
15/05/2026 Duration: 07minToday 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 chat. Have a money question? Email us here Subscribe to
-
I’m 45, Can I Quit My Job?
14/05/2026 Duration: 13minGiven 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 Subscribe to Jill on Money LIVE Subscribe to
-
In My 60s and Feeling Concerned
13/05/2026 Duration: 17minNow 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 Subscribe to Jill on Money LIVE Subscribe to
-
Are We on the Right Track at 42?
12/05/2026 Duration: 30minNow that we're in our 40s I'm starting to have major concerns about our financial roadmap. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
-
Real Estate Loan Dilemma
11/05/2026 Duration: 20minWith 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 Subscribe to Jill on Money LIVE Subscribe to
-
Transitioning Back Into the Workforce
08/05/2026 Duration: 24minAs 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 Subscribe to Jill on Money LIVE Subscribe to
-
Prepping for Retirement at 53
07/05/2026 Duration: 14minWith 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 Subscribe to Jill on Money LIVE Subscribe to
-
Realistic Next Steps for Living Life Now?
06/05/2026 Duration: 26minI 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 Subscribe to Jill on Money LIVE Subscribe to
-
Still on Track to Retire at 55?
05/05/2026 Duration: 18minWith 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 Subscribe to Jill on Money LIVE Subscribe to
-
Should I Stay or Take the New Job Offer?
04/05/2026 Duration: 16minShould 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 Subscribe to Jill on Money LIVE Subscribe to
-
Roth vs. Traditional
01/05/2026 Duration: 18minI'm struggling to make a decision in terms of pre-tax versus Roth. Will it matter in my situation? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
-
Can We Afford to Help Out Our Sons?
30/04/2026 Duration: 14minWith retirement right around the corner, can we afford to give our two sons a good amount of financial assistance? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to