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
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Should I Be Focusing on a Brokerage Account?
24/06/2026 Duration: 10minI'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 hereSubscribe to Jill on Money LIVESubscribe to
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Can I Change Jobs and Still Hit My Goals?
23/06/2026 Duration: 15minCan I downshift my career (work less, make less) and still hit my goal of retiring by 60?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Burnt Out After 42 Years in Corporate America
22/06/2026 Duration: 16minI'm 62, and after 42 years in the workforce, I'm wondering if I can comfortably retire?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Help With Mom’s Asset Allocation
19/06/2026 Duration: 16minMy mom is 75 and I'm helping her navigate her finances. Am I making the right moves?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Why Use Bonds?
18/06/2026 Duration: 15minYou 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 hereSubscribe to Jill on Money LIVE
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Can I Make a Career Change at 57?
17/06/2026 Duration: 14minI 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 hereSubscribe to Jill on Money LIVESubscri
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Can I Take My Pension and Run?
16/06/2026 Duration: 14minWe 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 hereSubscribe to Jill on Money LIVESubscribe to
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How to Fund a Renovation?
15/06/2026 Duration: 17minShould 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 hereSubscribe to Jill on Money LIVESubscribe to
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Does My Early Retirement Plan Work?
12/06/2026 Duration: 19minDoes my retirement plan work as is or should I be looking to buy a deferred income annuity?Have a money question? Email us hereSubscribe to Jill on Money LIVESubscribe to
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Where to Save in 30s and 40s?
11/06/2026 Duration: 21minBesides 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 hereSubscribe to Jill on Money LIVESubscribe to
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Investment Philosophy
10/06/2026 Duration: 11minHow 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 hereSubscribe to Jill on Money LIVESubscribe to
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Can I Retire in Four Years at 60?
09/06/2026 Duration: 14minI 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 hereSubscribe to Jill on Money LIVESubscribe to
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Are We Okay to Start Withdrawals?
08/06/2026 Duration: 24minWith 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 hereSubscribe to Jill on Money LIVESubscribe to
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Risk and Reward With Ben Carlson
05/06/2026 Duration: 32minToday 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 them so you can survive the short-term, and thrive in the long-term.Have a money question? Email us hereSubscribe to
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In Our 60s and Considering Retirement
04/06/2026 Duration: 20minMy husband and I are considering retirement and we would like guidance on whether it's financially feasible. Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to
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Roth or Not?
03/06/2026 Duration: 14minWith 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 Subscribe to Jill on Money LIVE Subscribe to
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Is Early Retirement an Option for Me?
02/06/2026 Duration: 13minWith 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 Subscribe to Jill on Money LIVE Subscribe to
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Do We Have Enough to Retire and Live Large?
01/06/2026 Duration: 23minMy 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 Subscribe to Jill on Money LIVE Subscribe to
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Get a Financial Life With Beth Kobliner
29/05/2026 Duration: 10minToday 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? Email us here Subscribe to Jill on Money LIVE
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Do I Still Need Term Life Insurance?
28/05/2026 Duration: 14minI'm 59 and my husband is 71, do we still need term life insurance? Have a money question? Email us here Subscribe to Jill on Money LIVE Subscribe to