500 episodes listed below
Real money questions, plain-spoken answers.
Jill on Money with Jill Schlesinger is a practical personal-finance advice show built around real listener situations. The conversations move from teasing banter to careful number-crunching, especially around pensions, Social Security, withdrawals, housing choices, and family obligations.
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Jill on Money with Jill Schlesinger is built around the financial choices people keep postponing because the numbers feel tangled. The show moves fast. A listener might arrive with pension options, a Roth conversion question, too much cash, a parent in assisted living, a military transition, or a plan to leave a high-stress job. Then the conversation slows down just enough to find the real decision. Jill and Mark ask for income, spending, savings, benefits, Social Security estimates, home value, debt, taxes, health, and timing. Nothing floats for long. A vague worry becomes a monthly cash-flow question. A retirement dream becomes a pension haircut, survivor benefit, withdrawal plan, or emergency-fund target. The tone is friendly, but it is not hand-holding for its own sake. Callers are nudged, teased, challenged, and then given a clearer frame for what comes next. That mix keeps the show from feeling like a lecture. It is more like sitting at a kitchen table with a sharp planner who wants every relevant number before giving an opinion. The recurring listener calls give the advice texture because the same topic rarely means the same thing twice. Cash can be safety or procrastination. A bigger house can be a life upgrade or a drag on flexibility. A pension can create freedom, but only if health coverage, survivor income, and timing line up. Episodes also make room for broader investing conversations, including Ben Carlson’s discussion of market volatility, rules, and long-term wealth. The show’s best moments come when it turns financial anxiety into a specific planning tradeoff. It is practical, skeptical, and more conversational than glossy. For people nearing retirement, managing parents’ money, raising kids, or trying not to make one expensive mistake, it offers useful pressure testing without much ceremony.
Made for: Designed for adults making consequential household money decisions, especially around retirement, pensions, Social Security, college costs, home purchases, aging parents, and career transitions. It fits listeners who have saved seriously but want help turning balances and benefits into a plan.
What sets it apart: The show’s strength is the live diagnostic style: every answer is built from the caller’s actual numbers, not from generic rules. Jill and Mark combine quick banter with persistent follow-up questions, so the advice stays human and specific.
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 each week 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.
This is where your six-figure question gets follow-up questions, arithmetic, and an actual answer.
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Short reviews from the PlayNext desk, based on the episodes we processed.
Jill turns a possible career break into a two-year planning question, with savings, reserves, housing, and future work all still in view.
Jill Schlesinger treats Amber's wish to quit at 38 less as a retirement fantasy than as a test of whether a two-year pause can sit inside a household that is already saving hard.
A practical look at how pension, Social Security, and mortgage timing shape retirement cash flow.
Jill Schlesinger turns a familiar retirement worry into a practical cash-flow question: how to keep family expenses covered while a household moves toward pension income, Social Security, and the end of a mortgage.
Frugality without the shame spiral.
Money rules for real-life tradeoffs.
Evidence before investing conviction.
Abundance coaching with a devotional pulse.
A 58-year-old federal employee with $175,000 in 529 plans wonders if he should use them for his kids' Catholic high school tuition.
Amber, 38, asks if she can quit her job because her husband thinks they can survive on his $81,000 income alone.
Jane in Seattle expects an unexpected $1.75 million inheritance, and Jill Schlesinger advises planning before investing or spending it.
Jill Schlesinger and Mark assess whether Danny and his wife, both 60, can retire around 2027 with about $1.94 million saved.
Jill Schlesinger says job hoppers in research from Rutgers and Cornell settle into new roles in two months, compared with five months for the average worker.
Jill Schlesinger and Mark answer listener questions about Roth conversions, retirement timing, housing debt, student loans, and monthly spending.
Jill Schlesinger and Mark advise Anne, age 36, and her 41-year-old wife on organizing retirement, cash, college, housing, insurance, and estate planning.
Jill Schlesinger and Mark Talercio advise Kathleen, a 57-year-old Rhode Island caller, on whether her disabled 60-year-old husband can begin 401(k) withdrawals.
Jill Schlesinger interviews Ben Carlson, Director of Institutional Asset Management at Ritholtz Wealth Management, about his book Risk and Reward and long-term investing.
A caller seeks advice on managing his 87-year-old mother's finances, including whether to move inherited IRA stock funds into safer investments like CDs to cover her $10,000/month assisted living costs.
This episode addresses a listener's question about planning around government pensions and medical benefits in mid-career, with promotional content for a subscription service and an upcoming social security webinar.
A military member planning to transition out of service in about a year and a half seeks advice on managing emergency fund savings and financial planning with a $6,500 monthly pension while considering family needs and future employment.
A couple in their 50s with high-stress jobs and substantial savings seeks financial advice on transitioning to new life goals as their last child enters college.
A financial advice podcast episode where host Jill helps Mona, a 57-year-old business owner and teacher, with questions about managing her finances and planning for retirement.
This episode of the Jill on Money Show features a discussion with a listener named Kat about her financial anxiety and struggles with retirement planning, offering non-judgmental advice from certified financial planners.
A 58-year-old caller named Mark seeks advice on balancing retirement savings with using 529 accounts to pay for his adopted teenagers' Catholic high school and college tuition.
This episode features an interview with Shea Wong about how his new company Helgo helps people navigate AI's impact on careers and the job market.
This episode features a caller named Jane from California who was recently laid off, seeking advice on whether she needs to find another job and related financial guidance.