Jill on Money with Jill Schlesinger

Episode: Feeling Stuck as I Approach Retirement
Date: December 30, 2025
Guest: Jackie (Caller from Nevada)

Episode Overview

In this episode, Jill Schlesinger takes a call from Jackie, a 63-year-old listener from Nevada, who is feeling stuck as she approaches retirement. Jackie is anxious about her investment choices after moving all her assets into “safe havens” following a market downturn years ago. Jill walks Jackie through a comprehensive review of her retirement readiness, breaking down her income sources, assets, and options for managing the emotional and practical challenges of transitioning into retirement.

Key Discussion Points and Insights

1. Jackie’s Retirement Snapshot

[02:58 – 07:20]

• Jackie, 63, plans to retire around age 65, currently working part-time (earning ~$12,000/year).
• Income sources in retirement:
  • Small pension: $800/month
  • Business income: ~$2,000/month, business equity valued at ~$500,000
  • Husband’s Social Security: $1,500/month (he's been retired ~6 years)
  • Jackie’s future Social Security: ~$2,600/month at full retirement age, $3,000/month at age 70
• Estimated monthly expenses: $6,000
• Assets:
  • Jackie’s 401(k): $430,000 (in stable value fund)
  • Husband’s 401(k): $200,000 (also in stable value)
  • Cash/non-retirement accounts: $200,000 (bank), $400,000 (brokerage, in stable value)
  • Home: Paid off, valued at ~$600,000
• No children, planning to leave assets to family (sister, nephew); no pets.

2. Current Asset Allocation and Risk Aversion

[06:37 – 07:32]

• Post-market crash, Jackie and her husband moved nearly all assets into stable value or cash equivalents due to fear of losses.
• Jackie wants to do “better” but is hesitant and lacks confidence re-entering the market.

3. Encouraging Strategic Allocation & Accepting Volatility

[10:58 – 13:49]

• Jill suggests a gradual approach to re-investing:
  • Start by shifting a modest portion (e.g., 10–25%) into equities and bonds.
  • “Your allocation would literally be 10% fixed income, 10% equities, and 80% stable value. Do you think you could live with that?” (Jill Schlesinger, 12:43)
• Jackie responds positively: “Not when you put it like that.” (12:43)
• Jill encourages making these changes within the old 401(k) accounts to start, emphasizing it's okay to proceed slowly: “It's like a little bit like we're dipping your toe in the water.” (13:51)

4. Social Security Strategy

[13:56 – 16:44]

• Jill analyzes the pros and cons of delaying Jackie’s Social Security to age 70:
  • Maximizes benefit significantly (from ~$2,600 to $3,200/month)
  • Requires drawing down savings to cover the income gap ($100,000 over 3 years)
• Jill: “Can you give yourself permission to spend the hundred? Because it’s kind of nice to get that guaranteed big bump up to maximize your Social Security benefit.” (14:45)
• Jackie: “Yeah, well, that's what it’s for. But it’s like, oh, yes, I know, I know. Run out.” (16:50)

5. Emotional Challenge of Spending Down Savings

[16:50 – 17:20]

• Jill discusses the psychological hurdle many retirees face: the transition from accumulating to decumulating assets.
  • Jill: “There’s a fancy term for this in financial planning… it’s the problem of the accumulator versus the decumulator. It’s a very hard transition.” (16:56)
• Jackie agrees, acknowledging the difficulty.

6. Tax-Saving Strategy: Roth Conversions

[09:34 – 09:58]

• Jill suggests converting a portion of the husband’s IRA to a Roth IRA while still in a low tax bracket.
  • "Only convert enough so that you'd stay in that 12% tax bracket because your income is low... Or you don't have to. You really don't have to.” (10:01)

7. Estate Planning Reminder

[17:34 – 17:47]

• Jill urges Jackie to complete her estate planning (wills, documents).
  • Jackie: “Well, that’s on the to-do list.”
  • Jill: “All right, let’s put that higher up on the list.” (17:44)

Notable Quotes & Memorable Moments

• On Facing Retirement Fears:
  "I really would like to get back in there, but I'm afraid. I'm afraid to lose the money and I don't know exactly what to."
  — Jackie (07:32)

• On Rebalancing Investments:
  “If I looked at your total assets... all I’m asking you is could I put 100,000 of that million in stocks? Can I put 100 of that million into bonds? ... That doesn’t seem like a lot to me.”
  — Jill Schlesinger (12:10–12:43)

• On Delaying Social Security:
  "It’s kind of nice to get that guaranteed big bump up to maximize your Social Security benefit. Most people can’t afford to do it… but it will require you to spend down some of your money, and you’ve got to be okay with that."
  — Jill Schlesinger (14:44–14:56)

• On Emotional Hurdle of Drawing Savings:
  "The problem of the accumulator versus the decumulator. It’s easy to accumulate... It’s a much harder transition to go from putting money in to taking money out."
  — Jill Schlesinger (16:56–17:12)

• On Estate Planning:
  “Let's put that higher up on the list.”
  — Jill Schlesinger (17:44)

Timestamps for Key Segments

• Jackie's Background & Income Sources: [02:58 – 07:20]
• Asset Allocation History & Motivation: [06:37 – 07:32]
• Strategy for Gradual Portfolio Risk: [10:58 – 13:49]
• Discussing Social Security and the Psychology of Spending Down: [13:56 – 16:50]
• Roth Conversion & Tax Planning: [09:34 – 10:01]
• Estate Planning Message: [17:34 – 17:47]

Tone and Style

Jill remains characteristically warm, straightforward, and jargon-free while guiding Jackie. She balances empathy for Jackie’s emotional struggles with practical, actionable advice, encouraging a step-by-step and manageable approach to financial change.

Summary Takeaways

• Jackie is in a strong financial position with multiple income sources and substantial savings.
• Her “stuck” feeling is rooted in risk aversion and emotional difficulty with shifting from saving to spending—incredibly common among new retirees.
• Jill recommends a gradual reentry into the market with a small allocation to stocks/bonds, possible strategic Roth conversions, and considering delaying Social Security for a higher benefit.
• Emotional readiness for decumulation and completing estate planning are highlighted as equally essential retirement tasks.
• "Let me know how it goes. I want a screenshot of when you pull the trigger and buy some stocks." — Jill Schlesinger (17:23)

For listeners approaching retirement unsure about investment moves or spending down savings, this episode offers reassuring, stepwise strategies and underscores the emotional as well as financial aspects of retirement planning.