Podcast Summary: Jill on Money

Episode: 10 Years Until Retirement, Can I Do It?
Host: Jill Schlesinger
Date: March 31, 2026

Overview

In this episode, Jill Schlesinger speaks with listener Kay from Florida, who is ten years out from retirement and seeking a progress check on her financial readiness. The conversation centers on realistic retirement planning for late starters, resilience in the face of life setbacks (such as divorce), and practical strategies for financial security without having "millions" saved. Jill and her producer Mark offer encouragement, expert analysis, and relatable advice for listeners navigating similar circumstances.

Key Discussion Points and Insights

1. Kay’s Financial Snapshot

• Age: 55, aiming for retirement at 65

• Work: Full-time, annual income of $103,000

• Retirement Savings:

  • 4% workplace retirement plan with a $61,000 balance; employer matches contribution
  • Traditional IRA rollover: $220,000 (Vanguard)
  • Roth IRA: $115,000, contributing $550/month
  • Brokerage account: $5,000 (money market fund, contributing $50/month)

• Additional Savings:

  • High-yield savings: $30,000
  • I Bonds: $5,000
  • Robinhood/Acorns accounts: ~$5,000

• Children:

  • Son (24, financially independent)
  • Daughter (20, in college); college fully funded via prepaid plan and 529

• Housing Situation:

  • Owns home purchased in 2020 ($240,000 purchase, $315,000 current value)
  • Mortgage: $148,000 balance, 2.62% interest (30-year fixed)
  • Not making extra principal payments, per Jill’s advice—redirects surplus to retirement

2. Current Expenses and Lifestyle

• Monthly Expenses: Approximately $5,000 (excludes retirement contributions)
• Lives frugally: cooks at home, does own yard/housework
• Side hustle: thrifting and reselling on eBay to fund travel (e.g., recent 2-week trip to Japan)

3. Future Projections and Planning

• Social Security: Expects $3,000/month

• Retirement Contributions: Continuing for next 10 years (~$7,200/year to Roth + workplace savings)

• Long-term Outlook: On track for $800,000+ in retirement savings if contributions continue

• Family Considerations:

  • Aging mother (92, Tennessee): Some financial support, but mother has resources (long-term care insurance, paid-off home, Social Security)

Notable Quotes & Memorable Moments

On Late Starts and Progress

• Kay [03:08]:
  "I'm hoping you'll give hope to those that are kind of starting late in life and getting their finances together... I want to see how I'm doing."

• Jill [03:41]:
  "You don't have to have millions always. You know, it's a lot of different ways to get where you want to go."

On the Mortgage Sweet Spot

• Kay [07:20]:
  "It is a 30 and Lord, I want to pay extra, but I—"

• Jill (interrupting with laughter) [07:24]:
  "No, no, I don't. I listen to you guys. You tell me and I just put the extra in my retirement plan."

  • Jill [07:30]:
    "Perfect. That's great."

On Family and Longevity

• Kay [08:34]:
  "I do have an aging mom. She's 92, she lives on her own, still drives."
• Mark [08:41]:
  "Oh my God."

Jill’s Encouragement and Assessment

• Mark [10:36]:
  "She needs to give herself some credit from where she was to where she is... that's going to be over $800,000 in 10 years. Doesn't spend a lot of money."

• Jill [10:49]:
  "I think that you are an amazing example of, you know, the rug kind of gets pulled out from under. You certainly didn't think, you know, probably 30 years ago, you didn't think, oh, I'm going to be getting divorced when I'm 45. But here you are. But you're doing a great job."

• Jill [12:59]:
  "Well, I think you're doing an amazing job and we salute you. And Kay, you're in great shape and we really appreciate you checking in with us and we wish you all the best, truly."

Important Segments & Timestamps

• [02:05] – Jill introduces listener Kay and frames the theme (starting late, realistic retirement goals)
• [03:08-07:46] – Kay details her financial picture, savings, kids' college, and homeownership
• [07:47-10:36] – Social Security expectations, continued saving, and handling family support
• [10:49-12:59] – Jill and Mark offer encouragement; exploring part-time work, side hustles, and quality of life
• [12:27] – Kay shares about thrifting, eBay resales, and funding travel with side gigs

Tone & Takeaways

• Tone: Supportive, practical, down-to-earth, and encouraging
• Main Takeaways:
  • It's possible to rebound from late starts or setbacks and create a secure path to retirement.
  • Consistent saving, realistic spending, and making use of low interest rates can set you up for success—even without a huge nest egg.
  • Creative side hustles and resourcefulness (like travel-funding resale) can enhance both now and the future.
  • Listeners are reminded that they don’t have to be “millionaires” to receive support and financial advice on the show.

Final Words

If you’re working towards retirement and feel behind, Kay’s story exemplifies what focus and discipline can accomplish within a decade. Jill and Mark underscore that personalized strategies and small, steady actions are key. The episode closes with an invitation for listeners in any situation to reach out for their own financial check-in.

For more listener questions or to join the conversation, visit: jillonmoney.com