
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 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.
Latest episodes

11 snips
Apr 23, 2025 • 17min
On Track for Retirement in Seven Years?
Discover strategies for maximizing retirement savings and effectively managing debt. Explore the financial landscape of a 60-year-old navigating investments and pension benefits. Dive into the challenges faced by investors dealing with market volatility and real estate values. Learn about personal finance techniques essential for planning around special needs care. Finally, get insights on creating a balanced portfolio tailored to individual goals, emphasizing the importance of asset allocation and risk management.

10 snips
Apr 22, 2025 • 12min
Convincing Hubby We Have Enough
A listener grapples with her husband's fears about retirement, revealing underlying emotional dilemmas beyond finances. The hosts emphasize the importance of humor and positivity in navigating money issues. They dive into the transition challenges of retiring from a steady income, crafting strategies to ease the journey. Engaging topics include how financial decisions impact relationships and the necessity of open communication in tackling financial insecurities. Plus, they share their favorite comedic shows to lighten the mood!

5 snips
Apr 21, 2025 • 17min
Am I Okay to Retire in a Year?
The hosts dive into the maze of retirement planning, offering insightful guidance on pension benefits and Social Security strategies. They emphasize the advantages of delaying benefit claims until age 70 for enhanced financial security. Tax implications from selling rental properties are also discussed, including capital gains and depreciation recapture. Listeners get practical advice on managing finances, covering everything from real estate investments to monthly expenses, ensuring a well-rounded approach to preparing for retirement.

12 snips
Apr 18, 2025 • 19min
Concerns About My Financial Advisor
Concerns about financial advisors spark intriguing discussions. Strategies for navigating personal finance in uncertain times are explored. Key topics like estate planning and retirement investments take center stage. The podcast emphasizes the importance of liquidity in today's market. Listeners are encouraged to engage, highlighting the challenges of making sound financial decisions amidst personal relationships.

4 snips
Apr 17, 2025 • 12min
Good Time to Increase Roth Conversions?
Explore the tactical benefits of increasing Roth conversions during economic downturns, emphasizing the importance of individualized assessments. Dive into retirees' financial concerns amidst market anxieties and learn the value of proactive engagement with financial representatives. Discover strategies for managing investments and taxes in uncertain times, highlighting the careful approach needed to navigate market fluctuations. Plus, uncover community support resources and tools that empower listeners on their financial journeys.

5 snips
Apr 16, 2025 • 19min
Anxious About Retirement Plan
This podcast tackles the anxiety many face while preparing for retirement amid financial volatility. A light-hearted discussion leads into serious advice, as a couple's financial readiness is examined. Key topics include retirement account strategies like 401ks and the importance of asset allocation. Listeners learn about managing emotions and fixed expenses during this life transition. Insights on estate planning and the advantages of choosing reliable financial partners are also explored, making it a must-listen for those approaching retirement.

Apr 15, 2025 • 15min
Conflicted About Early Retirement Offer
This discussion dives into the decision-making dilemma of accepting a buyout for early retirement. It explores financial readiness, including how pension income and housing obligations play critical roles. Listeners hear personal stories that weigh job satisfaction against the allure of severance packages. The emotional aspects of financial security are highlighted, encouraging mindfulness in choices that resonate with individual values. Ultimately, it’s about finding empowerment through uncertainty.

Apr 14, 2025 • 16min
Can I Use the Rule of 55 and Retire?
I don’t like my job. So, do I take the leap now, or push through for a few more years? What are the real pros and cons beyond just the numbers?Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoney"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Apr 12, 2025 • 11min
Introducing: What We Spend
Imagine if you could ask someone anything you wanted about their finances. On What We Spend, people from across the country and across the financial spectrum are opening their wallets—and their lives—to tell you everything: what they make, what they want, and—for one week—what they spend. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

Apr 11, 2025 • 20min
How Risky Can I Be With a Career Reset?
How comfortable should I be with our financial situation in order to help us determine how much time I can afford not generating income and weigh the options for what the next opportunity could be?Have a money question? Email us hereSubscribe to Jill on Money LIVEYouTube: @jillonmoneyInstagram: @jillonmoneyTwitter: @jillonmoney"Jill on Money" theme music is by Joel Goodman, www.joelgoodman.com. To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices