

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

12 snips
Aug 4, 2025 • 22min
Need to Find Peace and Get Some Time Back
Discover strategies for reclaiming your time and finding peace amidst financial chaos. Hear real-life experiences of balancing work and parenting while planning for college expenses. Explore the intricacies of education compensation and retirement preparation. Learn how to navigate life insurance choices with a focus on community support. Each insight offers a unique perspective on achieving work-life balance and financial stability.

11 snips
Aug 1, 2025 • 16min
55 With the Itch to Retire
Listeners dive into the pressing question of retirement timing as they ponder life after 58. Strategies to maximize pension and Social Security benefits are highlighted, alongside personalized advice for managing finances. The challenges of entrepreneurship are also discussed, emphasizing the diverse roles business owners take on and introducing a global commerce solution to streamline their efforts. Tune in for engaging insights and expert guidance to navigate your financial future!

15 snips
Jul 31, 2025 • 20min
Get Out of Here and Enjoy Your Life
Explore the journey of transitioning to part-time work in retirement and the importance of financial planning. Discover strategies to navigate personal finances after major life changes, like divorce, including insights on 403B accounts. Dive into retirement choices, contrasting pensions with annuities, and the significance of work-life balance. Finally, learn about the 'glide path' approach to retirement, emphasizing proactive health decision-making and positive daily actions in a changing world.

12 snips
Jul 30, 2025 • 21min
Navigating Single Life in My 50s
Navigating life in your 50s brings unique financial challenges. The discussion centers on the complexities of long-term care insurance, especially for single women. Listeners explore retirement readiness, including pensions and savings strategies, while considering future expenses. Insights into managing long-term care and retirement funding shed light on essential planning aspects. The podcast emphasizes making informed financial decisions amid evolving job markets and career transitions.

10 snips
Jul 29, 2025 • 20min
High Earners, Still Do Roth?
The discussion kicks off with the challenge of managing finances amidst job changes and how job satisfaction plays a role in financial health. High-income listeners share their reflections on tax strategies, especially regarding Roth versus traditional retirement accounts. Recent tax legislation impacts are examined, focusing on SALT deduction limits and the need for tailored advice. The importance of balancing immediate tax benefits with long-term savings is emphasized, along with the necessity to rethink financial strategies in light of potential future tax increases.

8 snips
Jul 28, 2025 • 17min
Is There an Alternative to Annuities?
In this discussion, the pros and cons of annuities are examined as listeners consider their financial futures. There's a deep dive into early retirement preparations, including expenses and healthcare. The impact of potential relocations on finances and housing is also explored. Additionally, the drawbacks of multi-bucket strategies are highlighted, emphasizing the need for accessible funds and second opinions from certified planners. Overall, it stresses informed decision-making in navigating complex financial products.

12 snips
Jul 25, 2025 • 15min
60 and Planning for Retirement at 67
A listener navigates their retirement plans, wondering if they're on track for a secure future. The discussion dives into income sources like Social Security and pensions. Key strategies for withdrawing from retirement accounts are explored, alongside the timing for claiming benefits. The importance of managing minimum required distributions is highlighted, with tips on tax implications. Investment strategies focusing on low-cost index funds are also examined, encouraging personalized advice for a solid financial path.

10 snips
Jul 24, 2025 • 17min
Job Change With No 401(k)
Explore the impact of AI on jobs in finance and media, as experts discuss its limitations compared to human experience. Learn how to navigate 401(k) transitions during a job change and weigh the pros and cons of lump sum versus monthly pension payouts. Gain insights into retirement strategies, from life insurance to Social Security claims, and discover effective saving methods. The importance of timing withdrawals and maximizing contributions is emphasized, making financial planning feel empowering and accessible.

4 snips
Jul 23, 2025 • 15min
Federal Service Early Retirement
The podcast dives into the significance of making smart financial moves during key life events like retirement. It discusses the retirement plans for federal employees, emphasizing pensions, spousal benefits, and Social Security. Listeners learn about managing personal retirement savings, including the ins and outs of IRAs. A couple shares their thoughts on approaching retirement, focusing on finances and aspirations. Finally, the importance of estate planning is highlighted, reassuring listeners about securing their financial future.

5 snips
Jul 22, 2025 • 14min
529 Plans vs Trump Accounts
The discussion dives into the new Trump Accounts and whether they outshine traditional 529 plans for college savings. Listeners hear about the complexities of timeshare exits and retirement planning challenges, including healthcare costs. The balance between leaving a legacy for children and enjoying retirement is explored, emphasizing experiences over mere savings. Finally, the notion of financial independence is celebrated, likening it to the freedom of summer vacation and encouraging listeners to engage with their financial journeys.