Podcast Summary: Jill on Money with Jill Schlesinger
Episode: Buckets in Retirement
Date: November 20, 2025
Main Theme & Purpose
In this episode, host Jill Schlesinger, CFP®, takes a listener call from Stacy in Washington State for a "retirement check-in." The primary focus is on organizing financial "buckets" for retirement—how to allocate and withdraw funds from various accounts, whether Stacy is on track to retire at age 57, and which adjustments might make her retirement finances more secure. It's an in-depth, real-world look at practical retirement strategy with an emphasis on flexibility and risk management, served up with Jill's trademark candor and warmth.
Key Discussion Points & Insights
1. Stacy's Situation: The Quick Facts
[03:34–06:31]
- Stacy is 53, partnered (they share expenses but keep finances separate), with no children.
- Owns her home (worth ~$800,000), mortgage-free.
- Earns $150,000/year, planning to retire at 57, transitioning to part-time work for three years prior.
- Substantial savings: $1.2M in a traditional IRA, $85K in Roth IRA, $25K in Roth 403(b), $55K HSA, $260K in a brokerage account, plus $15K in liquid cash.
2. Planned Retirement and Withdrawal Strategy
[06:31–10:44]
- Stacy intends to retire at 57 (full stop at 57 after part-time transition), then live off the brokerage account until eligible for retirement account withdrawals at 59½.
- She will have a state pension of $1,300/month starting at 65 (with a COLA), and expects Social Security of ~$3,470/month at 67.
- Annual expenses are modestly estimated at $4,000/month, likely to increase to ~$5,000/month in retirement due to health insurance and travel.
Jill's Analysis of the Plan
- Jill supports drawing down the brokerage for the “gap years” (57–59½) and then tapping into the traditional IRA.
- She's impressed by Stacy's savings and controlled lifestyle.
“Mark, what is with this? These people, they're $4,000 a month. I'm, like, so jealous.” — Jill, [08:29]
3. Risks and Flexibility in Early Retirement
[11:31–16:12]
- Jill highlights the risk of a severe market downturn in the years leading up to and just after retirement:
“Is it possible between now and the next four years that we have a big market sell-off and that all of a sudden your, you know, $1.3 million…gets lopped into 900 grand?... I personally would never want to retire into a bear market. If I had the choice, I would just keep working.”
— Jill, [13:02 & 15:13] - Jill recommends flexibility: either staying full-time longer or working part-time for more years, depending on how the markets and Stacy's assets fare.
- The idea is to "retest" the plan in a few years to ensure security, especially if the market tanks before or in early retirement.
4. Roth Conversions, Health Care, and Expense Planning
[11:31–13:50, 12:05–12:31]
- Stacy inquires about small Roth conversions in the early retirement years. Jill advises prioritizing liquidity:
“I need your money. Okay, we need that money for sure.” — Jill, [11:45] - Health care coverage post-retirement is available via Stacy's state employment, but will cost about $1,000/month—not yet included in current expense estimates.
- Jill urges caution about underestimating expenses and the impact of inflation and health care costs.
5. Asset Allocation Before Retirement
[16:46–17:19]
- Stacy asks if saving money in a high-yield account versus the brokerage makes sense for greater liquidity as retirement nears.
- Jill suggests splitting savings between the brokerage and high-yield accounts:
“I would really look at brokerage and high yield savings. Those two. That's what I would do for sure. Just to preserve that early retirement optionality.”
— Jill, [17:15]
6. Estate Planning & Final Advice
[16:40–16:42]
- Stacy confirms she’s set up her estate plan.
- Jill concludes that success in Stacy’s plan depends on being flexible and revisiting the plan as markets and personal situations change.
- The “dream” is alive, but the real key is adaptability as circumstances evolve, not a rigid commitment to a date or drawdown schedule.
Notable Quotes & Memorable Moments
- Jill’s humor about modest lifestyle:
“Mark, what is with this? These people, they're $4,000 a month. I'm, like, so jealous.”
[08:29] - On the “bear market retirement” dilemma:
“I personally would never want to retire into a bear market. If I had the choice, I would just keep working.”
[15:13] - Jill urging practical caution:
“53 is really young. You could live for 40 years… once we get into your 60s, you're good, but it's a long time to get there. So 10 to 13 years of just pulling money out of your retirement account is something that can be a little edgy.”
[14:08] - On partnering with someone less wealthy:
“Is your partner, like, much richer than you?”
“No, much less rich than me.”
“That's terrible. What were you thinking? What on earth were you thinking, for God's sakes?”
[13:50]
Important Timestamps
- [03:34] — Introduction of Stacy and overview of her finances
- [06:31] — Retirement accounts and withdrawal timing
- [08:29] — Discussion about expenses and lifestyle
- [10:43] — Tax considerations in Washington State
- [11:31] — Withdrawal strategy and Roth conversion question
- [12:05] — Health care costs in retirement
- [13:02] — Jill's concern about market risk and flexibility
- [15:13] — Advice about retiring in a bear market
- [16:40] — Estate planning confirmation
- [16:46] — Liquidity versus brokerage for pre-retirement funds
- [17:15] — Jill's summary on where to save next
Conclusion
Flow & Takeaway:
This episode delivers a realistic, reassurance-laden approach to retirement planning. Jill’s guidance embodies both empathy and professional caution, emphasizing that even well-prepared savers like Stacy need to stay nimble and be ready to change course in the face of market volatility. The tone remains light, encouraging, and sensible throughout.
Listeners left with two main lessons:
- Plan meticulously, but be ready to adapt if the investing landscape shifts.
- Prioritize liquidity approaching retirement, and err on the side of caution with early drawdowns.
Jill’s invitation: If you’re tackling similar questions and want a tailored conversation, reach out to the show!