

Jill on Money with Jill Schlesinger
Audacy
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.
Episodes
Mentioned books

18 snips
Sep 5, 2025 • 28min
Feeling Lost, What's the Next Step?
The discussion kicks off with insights on the rise of contract talent post-Labor Day and the multifaceted services of Amazon Prime. A chaotic travel tale from China leads into the importance of estate planning. Listeners hear a family's inspiring financial journey from modest savings to significant wealth, alongside the challenges faced by their adult children. Retirement finances are unpacked, covering social security and investment strategies. Finally, there's a focus on tailored wealth management for immigrant families, including tax liabilities and aligning financial goals.

Sep 4, 2025 • 17min
Income Streams in Retirement
What's the best way to manage four different annuities, plus Social Security, during my retirement years?
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16 snips
Sep 3, 2025 • 13min
59 and Considering Retirement
Delve into the complexities of retirement planning, illustrated by a case study of a couple's financial landscape. Discover strategies to maximize your retirement income, including pensions and 401k options. Unpack the emotional challenges of job dissatisfaction and how they can shape your retirement choices. Learn the significance of effective financial management during retirement transitions and the importance of estate planning. Gain insights into working with a financial planner to secure your financial future.

22 snips
Sep 2, 2025 • 15min
In-Plan Roth Conversions
Get ready for a deep dive into in-plan Roth conversions available to federal employees starting in 2026! Discover effective strategies to manage tax payments and navigate retirement planning tailored for a 45-year-old single employee. Learn how to retire early without Social Security and leverage government pensions. Explore investment strategies, insurance coverage, and smart savings options, like CD ladders, to maximize returns. Finally, empower your financial future with sustainable wealth-building strategies, particularly with rental income!

5 snips
Sep 1, 2025 • 10min
Lump Sum or Monthly Payments?
In this discussion, the hosts assist a listener in navigating tricky pension options. They weigh the benefits of lump sum payouts against monthly payments, shedding light on how each choice affects long-term financial security. The conversation highlights the need for careful consideration of individual circumstances and financial goals. Additionally, they touch on the importance of estate planning and seeking professional advice to ensure peace of mind in retirement. The session is full of practical insights for anyone approaching retirement.

14 snips
Aug 29, 2025 • 14min
On Track as We Approach Retirement?
As retirement looms, the conversation delves into the importance of assessing financial health. A couple reveals their retirement planning journey, discussing account figures and effective strategies. Key topics include the management of traditional IRAs and 401(k)s, along with understanding investment fees. Emotional aspects of transitioning to retirement are explored, alongside timely social security strategies. Additionally, the discussion touches on the role of young adults in supporting parents financially, showcasing how it can reinforce family ties.

12 snips
Aug 28, 2025 • 15min
Should I Ditch the Target Date Fund?
Listeners dive into the pros and cons of ditching target date funds for more aggressive investments. The conversation explores the importance of examining personal risk tolerance and market volatility. A compelling strategy emerges, suggesting an 80% stock to 20% bond allocation. Emphasis is placed on balancing investments with savings for financial security. Plus, the hosts encourage seeking professional advice as year-end approaches, making it a perfect time for financial reflection and growth.

16 snips
Aug 27, 2025 • 20min
Can We Splurge a Little Bit?
How can we balance fun spending with financial goals? The discussion dives into managing leisure spending as retirement approaches, examining savings and income sources. Complex topics like irrevocable trusts and inherited wealth shed light on their tax implications and family dynamics. Real estate investment in a volatile market is covered, highlighting strategic decision-making and diversification. Finally, the importance of selecting the right financial advisor is explored, blending financial insights with a focus on enjoying life.

10 snips
Aug 26, 2025 • 18min
Should I Combine Accounts?
Listeners grapple with the question of whether to consolidate multiple retirement accounts as they approach retirement. The discussion delves into smart investment strategies and practical tips for managing finances in this new phase. Audience engagement is emphasized, with a call for suggestions on future topics. Plus, a spotlight on Shopify reveals how it can help aspiring entrepreneurs kickstart their online ventures.

22 snips
Aug 25, 2025 • 16min
Evaluating Pension Options
Explore the complexities of pension options and the nuances of survivor benefits in retirement planning. Hear a couple's journey as they navigate various payout scenarios, focusing on the impact of cost-of-living adjustments. The discussion expands to financial preparedness for retirement, emphasizing strategic planning for long-term security. Additionally, gain insights into effective estate planning and the importance of family discussions regarding resource allocation. It's a rich conversation about making informed choices for financial stability.