Podcast Summary: "Should I Collect Social Security Early?"

Podcast Information:

• Title: Jill on Money with Jill Schlesinger
• Host/Author: Audacy
• Description: Host Jill Schlesinger, CFP®, addresses sometimes uncomfortable and controversial money and investing issues without the financial jargon. Each week, Jill takes listener calls and interviews informative guests to uncover surprising insights and provide actionable information to help you make the most of your money.
• Episode: Should I Collect Social Security Early?
• Release Date: June 24, 2025

Introduction

In this episode titled "Should I Collect Social Security Early?", Jill Schlesinger and her co-host Mark delve into a variety of financial questions from listeners. While the primary focus is on the optimal timing for claiming Social Security benefits, the discussion spans several related financial topics, providing comprehensive advice to their audience.

Listener Questions and Discussions

1. Home Ownership vs. Renting

• Listener: Dan (04:15)

  Dan's Perspective: Dan, a long-time homeowner in Connecticut, questions the financial benefits of owning a home versus renting. After 36 years, he wonders if renting and investing the funds elsewhere would have been more advantageous, especially given the recent 45% spike in real estate values over the past five years.

  Jill's Response: Jill agrees with Dan's sentiment, highlighting two key calculations:

  • Rent vs. Ownership Costs: Comparing the total expenses of owning versus renting over the same period.
  • Investment Opportunity Cost: Evaluating what returns could have been generated if the money invested in the home was instead placed in a diversified portfolio.

  Notable Quote:

  “I do not think you should be able to deduct home mortgage interest on your taxes. I just don't.” – Jill Schlesinger (06:30)

  Jill also criticizes the tax code's bias towards home ownership, advocating for a more level playing field between renters and homeowners.

• Listener: Jerry (08:10)

  Jerry's Scenario: Jerry inquires about a family member who, after being widowed, holds significant savings and is considering whether to buy a new home or continue renting. Given her high income from various savings and infrequent use of her current home due to her job as a flight attendant, Jill advises that renting is more sensible.

  Notable Quote:

  “Renting is a no brainer. I think what we would really look at in her case would be, hey, if she's happy and she's got cash flow and the rent is reasonable, which it sounds like it is. Stay where you are.” – Jill Schlesinger (09:50)

2. High Yield Dividends and Reinvestment

• Listener: Rich (11:00)

  Rich's Inquiry: Rich asks about investing in a mortgage REIT that offers a 15% dividend yield. He is contemplating whether to reinvest the dividends or withdraw them, considering the volatility of the REIT's share price.

  Jill's Advice: Jill advises against daily monitoring of such investments. She recommends reinvesting the dividends to facilitate growth but warns about the tax implications of potential short-term capital gains if the shares are sold.

  Notable Quote:

  “Unless this is held in a retirement account, stop messing around with this. Just let it be. Make it part of your portfolio and that's it.” – Jill Schlesinger (13:20)

3. Should I Collect Social Security Early?

• Listener: Gary (14:00)

  Gary's Concern: Gary, aged 68, is contemplating whether to collect Social Security now or wait until 70, fearing potential shortfalls and means testing by the Social Security Administration.

  Jill's Response: Jill reassures Gary that waiting an additional two years should not pose significant risks regarding impending changes to Social Security. She suggests that delaying benefits until 70 will likely result in higher monthly payments without immediate threats to the system's integrity.

  Notable Quote:

  “If it's two more years, I wouldn't worry about that because I don't think they're going to be any changes to Social Security in two years.” – Jill Schlesinger (15:10)

4. Emergency Funds and Investment Growth

• Listener: Michael (16:00)

  Michael's Situation: Michael and his wife have established an emergency fund of $70,000 in a Schwab investor account but are unsure how to make the money work better while keeping it liquid.

  Jill's Recommendations:

  • Swapping to Higher-Yield Accounts: Move funds from the standard brokerage account to Schwab's money market funds, which offer better yields (e.g., 4.12% on the Schwab Prime Advantage money fund).
  • Building a Bond Ladder: Diversify with CDs of varying maturities to optimize interest earnings while maintaining liquidity.

  Notable Quote:

  “If you put one and a half percent of your total assets into this one mortgage REIT holding... I just can't believe it. This is such a scam for these funds.” – Jill Schlesinger (12:45)

5. Paying into Social Security While Living Abroad

• Listener: Grace's Friend (17:50)

  Grace's Question: Grace inquires on behalf of her 45-year-old friend who has lived abroad most of his life and never paid into Social Security. She seeks advice on whether it makes sense for him to start contributing now.

  Jill's Insight: Jill explains that eligibility for Social Security benefits requires earning income through employment covered by Social Security. If Grace's friend works for a U.S. firm or earns income tied to U.S. employment, he can contribute and eventually qualify for benefits. Otherwise, living and working solely abroad for a non-U.S. firm limits his ability to benefit from the system.

  Notable Quote:

  “If you can work for 10 years, accumulate 40 quarters of credits. Sure, why not?” – Jill Schlesinger (18:30)

6. Retirement Contributions vs. Cash Flow

• Listener: Stephanie (19:10)

  Stephanie's Dilemma: Stephanie, a stay-at-home parent, has an upcoming 12-month CD and is debating allocating funds between 529 plans for her children and taking a vacation. She seeks guidance on optimizing her retirement contributions against her current cash flow needs.

  Jill's Guidance: Jill suggests assessing whether retirement accounts are being maximized. If retirement contributions are already optimized, she recommends using the CD proceeds to fund 529 plans and allocate a portion for discretionary spending like vacations, emphasizing a balanced approach without sacrificing children's future.

  Notable Quote:

  “Maybe you can do a little bit of everything. So get back in touch with us. We would be delighted to walk you through this.” – Jill Schlesinger (20:40)

Conclusion

In this episode, Jill Schlesinger provides nuanced advice on various financial decisions, emphasizing the importance of individualized strategies based on personal circumstances. While addressing the primary question about the optimal timing for claiming Social Security, she also offers insights into home ownership, investment strategies, emergency fund management, and retirement planning. Listeners are encouraged to reach out via jillonmoney.com for personalized advice.

Notable Closing Quote:

“Change your work, change your wealth, change your life.” – Jill Schlesinger (16:28)

Additional Resources:

• Website: jillonmoney.com
• Newsletter: Available on Substack by searching "Jill on Money"
• Contact: Click the "Contact Us" button on the website to submit questions or join live on air.

This summary encapsulates the key discussions and insights from the "Should I Collect Social Security Early?" episode of "Jill on Money," providing valuable takeaways for both current listeners and those who haven't tuned in.