
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

Jan 17, 2025 • 13min
Investment Anxiety Entering 2025
Explore the lingering anxiety around investments as we head into 2025. Discover strategies for navigating market volatility, especially for those invested in the S&P 500. Learn about the significance of maintaining an emergency fund and the dangers of market timing. The discussion also highlights the challenges of real estate investing, complemented by an introduction to a managed portfolio solution. Plus, get a glimpse into new TV shows while diving deep into the world of finance.

Jan 16, 2025 • 20min
Roth Conversions, How Much and How Fast?
With over two million in tax-deferred accounts, and now that we're both retired, we feel now is the time for Roth conversions. How much should we do and how fast should we do it?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

Jan 15, 2025 • 12min
I Have a Pension, Do I Need Bonds?
Explore the intriguing idea of treating your pension like cash while contemplating riskier investments. Discover strategies for optimal retirement planning, particularly with substantial pensions and 401(k) funds. Delve into asset allocation and the potential market risks faced as you approach retirement. Learn about the importance of estate planning and preparing documents to secure your family's financial future. Get insights on balancing aggressive investment choices against the stability of pension income.

Jan 14, 2025 • 15min
Roth IRA or Roth 401(k)?
If I max out traditional contributions to my 401(k), it will lower my AGI and I'll be eligible to make Roth IRA contributions for me and my wife. Does that make sense? Or should I forget about the Roth IRAs and stick to the Roth 401(k)?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

Jan 13, 2025 • 19min
Moving Parts in Retirement
My wife and I are retired and we're trying to decide if we should start collecting Social Security and let our investments grow or should we take money from our brokerage account and do Roth conversions?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

Jan 10, 2025 • 22min
Can We Afford Our Forever Home?
A couple grapples with the financial realities of pursuing their dream home, weighing investment strategies and assessing mortgage affordability. They delve into the joys of homeownership and smart savings options, while also reminiscing about holiday culinary triumphs and childhood milestones. The conversation takes a fun detour into cycling and personal finance, addressing complex queries like treasury direct loans and I-bond rates. Heartfelt listener success stories illustrate the transformative power of sound financial advice.

Jan 9, 2025 • 13min
Can We Upgrade Our House?
Discover the intricate dynamics of real estate investment and how it can impact long-term financial goals. Delve into a family's financial stability while contemplating a major move and the emotional toll of selling their home. Hear about planning and strategizing a dream lake house purchase, balancing investments in IRAs and brokerage accounts. Explore the complexities involved in significant financial commitments and the importance of managing savings, income, and tax implications in high-stakes property transactions.

Jan 8, 2025 • 16min
55 and Thinking of Retirement
The journey to retirement at 55 brings financial complexities. Real estate investment is dissected, revealing its pros and cons. Stay informed about income sources and the dynamics of family finances as retirement nears. Dive deep into managing retirement accounts like IRAs and 401ks for strategic planning. Long-term care and insurance options are crucial for pre-retirees, alongside updating important estate documents to reflect life's changes. Prepare wisely to ensure a secure financial future!

Jan 7, 2025 • 15min
Planning for Our Financial Future
Explore innovative retirement strategies and essential tips for navigating family finances. Dive into proactive planning methods like Roth IRAs and 529 accounts for children's education. Discover how to optimize college funding while considering family income's impact on scholarships. Delve into the benefits of job flexibility in nonprofit careers and reassessing life insurance policies. Learn about vital estate planning tools like wills to secure your family's future against uncertainties.

Jan 6, 2025 • 18min
Anxiety Around My Finances
Explore the roots of financial anxiety and how early education shapes adult money habits. Discover smart strategies for retirement and effective debt repayment. Learn about investment management and the value of education savings plans, such as 529s. The discussion emphasizes the need for adaptability in finances and the significance of working with a financial advisor for personal stability. Plus, gain insights into the balance between family finances and future planning.