Podcast Summary: "Do I Have Enough to Slow Down?"

Podcast: Jill on Money with Jill Schlesinger
Episode Date: December 29, 2025
Host: Jill Schlesinger, CFP®
Episode Theme:
This episode addresses the financial, emotional, and practical considerations of "slowing down" or semi-retiring. Jill takes a listener call from Mary, a 63-year-old realtor, to analyze whether Mary is financially positioned to scale back from full-time work, while still maintaining her lifestyle, funding some travel dreams, and ensuring long-term financial security.

Main Theme & Purpose

Jill helps listeners wrestle with the common concern: "Do I have enough to slow down or semi-retire?" Working through Mary's numbers and circumstances, Jill illustrates principles about financial independence, spending, retirement tax strategy, and living out your dreams without fear or guilt.

Key Discussion Points and Insights

1. Introduction to Mary’s Situation (03:03–05:21)

• Who is Mary?
  • 63 years old, realtor, labeled herself a "worrier"
  • Wants to shift from full-time (7 days a week) to part-time, or possibly retire
  • Sold a townhouse, now owns a 2-bedroom, 2-bath condo mortgage-free ($325,000 value)
  • Savings: $1.6M in brokerage (mostly taxable), ~$500k cash, $400k in tax-advantaged accounts, $1,500/month ex-husband’s pension, Social Security eligibility

"I'm looking for some practical advice. I tend to be a worrier... I'm ready to slow down. So the question I have is: do I have enough reserves, savings, etc., to make that happen?" – Mary (03:10)

2. Analyzing the Numbers (05:22–07:39)

• Spending Needs
  • Comfortable on $4,000–$5,000/month; Jill assumes $5,000 for calculation
• Income Sources
  • $1,500/month pension (continues as long as ex-husband is alive)
  • Potential to make ~$1,500/month part-time (uncertain)
  • Social Security at age 70: Expected to be ~$3,700/month
  • Significant cash buffer: $500,000 sitting in a bank (immediate spending cushion)

"Let's just say that even if you do it for four or five...you take $50,000 a year out of that amount and you're covered, your expenses are covered..." – Jill (07:39)

3. Creating a Cash Flow and Withdrawal Plan (07:40–08:21)

• Jill suggests that Mary is financially secure enough to slow down now, drawing from her large cash reserve to fund living expenses during the gap years to age 70.
• Even if she draws $50,000/year for several years, there's sufficient cash and investments to ride out market swings and unforeseen expenses.

"You burn your cash, go through it, leave yourself with a couple hundred thousand dollars at the very end. By the time you're 70 and you are pretty well set..." – Jill (07:39)

4. Social Security and Pension Planning (07:08–08:29)

• Key consideration: Ex-husband’s pension ends upon his passing.
• The goal should be to delay Social Security until age 70 for maximum benefit, using savings to bridge the gap.

5. Roth Conversion & Tax Strategy (08:30–10:50)

• Jill raises the question of Roth conversions as a tax-preferential strategy while Mary is in a lower tax bracket (before RMDs and Social Security).
• Two strategies discussed:
  • Convert enough IRA to Roth each year to stay within the 22% bracket
  • Consider pushing into the 24% bracket because taxes are unlikely to go down

"I would start converting. I really would. You can use some of your cash. You're going to do it slowly over time. And if you do it, you've got like this 7-year horizon before you start taking Social Security..." – Jill (09:41)

6. Living Life: Travel and Enjoyment (10:50–11:47)

• Mary wants to travel more, especially to Italy where her sister has a place.
• Jill encourages spending on these enriching experiences, reassuring Mary that “slow down” includes living dreams, not just covering expenses.

"This sort of feels like there’s like many movies that are made about 60-year-old women who are traveling to Tuscany. So I think that you could just, like, binge all of those movies and figure out where you want to go." – Jill (11:24)

7. Estate Planning & Family Considerations (11:47–12:02)

• Mary confirms her will, health directive, and durable power of attorney are in order and under review.
• Children to be provided for by other family members.

Notable Quotes & Memorable Moments

• On Retirement Guilt & Freedom
  "Now that’s ridiculous [working 7 days a week]." – Jill (05:55)
  "I think you’re in great shape. Go find that Italian stallion. Exactly." – Jill (12:08)

• On Outliving Savings Anxiety
  "Yes, you could totally do this." – Jill (07:33)

• On Travel and Defying Stereotypes
  "If I could mesh Eat, Pray, Love and Under the Tuscan Sun…" – Mary (12:20)

Timestamps for Important Segments

• Mary’s introduction and concerns – 03:03
• Assets and spending details – 03:53–05:21
• Retirement income calculation – 05:22–06:50
• Social Security and pension analysis – 07:08–08:21
• Roth conversion discussion – 08:30–10:50
• Travel plans and lifestyle dreams – 11:07–11:47
• Wills and estate preparations – 11:47–12:02
• Final encouragement and wrap-up – 12:08–12:31

Episode Tone & Takeaways

The conversation is supportive, direct, and gently humorous. Jill’s hallmark style—cutting through worry, jargon, and guilt—shines through as she delivers a verdict: Mary can and should slow down, enjoy her savings, and pursue her travel and lifestyle wishes.

Listeners get a clear look at:

• Practical application of retirement math (spending vs. income and asset drawdown)
• The psychological hurdle of moving from saving to spending
• Timely tax strategy insights for those with significant pre-tax assets
• Importance of legal documents and communicating with family

Bottom line:
Mary is more than ready to slow down—and so might be many listeners in similar shoes, if they run their numbers with candor and care.

For further information or to submit your own question to Jill on Money:
Visit jillonmoney.com and click "Contact Us".