Jill on Money with Jill Schlesinger
Episode: Can We Make Our Dream a Reality?
Date: October 23, 2025
Host: Jill Schlesinger, CFP®
Special Guests: Annabelle from Washington State and her spouse
Main Theme
In this episode, Jill Schlesinger tackles Annabelle’s and her spouse’s financial planning questions, focusing on their upcoming retirement, withdrawal strategies, big-ticket purchases (a new car and a potential vacation home), and the reality check involved in trying to make their post-career dreams a reality. The tone is supportive, realistic, and pragmatic, with Jill offering both encouragement and tough love as needed.
Key Discussion Points & Insights
1. Retirement Preparedness Check (03:23–09:26)
- Situation:
Annabelle (55) and her spouse (61), both working full-time with a household income of ~$320,000/year; Annabelle has a second job and plans to work part-time into her 70s. - Retirement Savings:
- ~$900,000 in traditional retirement accounts.
- Both spouses will receive pensions:
- Spouse: $4,800/month at 65 (no COLA, includes survivor benefit).
- Annabelle: $6,000/month at 60 (2% COLA).
- Social Security expected in the future:
- Spouse: $3,150/month at 65, higher if delayed.
- Annabelle: $1,100/month at 67, $1,389 at 70.
- Spending Needs:
- ~$12,500/month including discretionary fun and some savings.
- Health insurance costs discussed, especially the gap before Medicare kicks in for Annabelle.
- Pensions + Social Security projected to cover most, but not all, spending.
Quote:
"It should just be giving you a framework to think about these big events in your life and maybe transitions that you're considering."
– Jill (01:30)
2. Withdrawal Strategies & Filling the Income Gap (09:26–13:41)
- Assets Beyond Retirement:
- $1.6M home (with $855,000 mortgage at 3.01%).
- Healthy but limited non-retirement savings: HSA (~$7,000), brokerage ($7,000), high-yield savings ($2,000).
- Bridging Gaps:
- Jill recommends they plan for additional withdrawals from their retirement accounts during early retirement years before Social Security, leveraging their likely lower tax bracket, especially given the lack of state income tax in Washington.
- Annabelle's potential part-time income ($2,500–$3,000/month) could help cover incidentals and reduce withdrawal pressure.
Quote:
"As long as you stay in a tax bracket that's reasonable—22, 24 percent—I think that you should be trying to get as much money out. And even if you take out more than you actually need... just pop that money that you don’t use into your brokerage account."
– Jill (12:56)
3. Big Purchase: Upgrading the Car for Travel (13:41–16:12)
- Dream:
- Buy a vehicle capable of towing their camper—a Toyota Sequoia, even used could be ~$60,000, new closer to $85,000.
- Questions Raised:
- Should they pay all at once out of retirement accounts or finance?
- Jill’s Take:
- Depends on loan rates at the time:
- If loan rates are reasonable (4–5%), consider financing and gradually withdrawing from retirement as needed.
- If rates are high (8–9%), better to take the full amount out, pay taxes, and buy outright.
- Suggests beefing up their brokerage and savings accounts in advance to increase flexibility.
- Depends on loan rates at the time:
Quote:
"It’s time for you guys to start looking at building up your brokerage account and that high yield savings account in anticipation of this car."
– Jill (16:02)
4. The Bigger Dream: Second Home/Vacation Property (17:04–22:39)
- Dream:
- Eventually buy a “small” vacation home, possibly in the Adirondacks ($350k–400k) or West Coast ($700k–800k).
- Jill’s Reality Check:
- Expresses strong concerns about withdrawing $400k–800k from retirement nest egg.
- Points out risks: significant depletion of liquid assets, increased exposure to unplanned expenses, and underestimating taxes on retirement account withdrawals.
- Suggests the only feasible way is to sell the primary home and downsize/trade to the dream locale.
- Recommends renting in vacation areas first to see if it’s truly right for them, and stresses the value of flexibility versus tying up net worth in illiquid real estate.
Quotes:
"You are young, you are 55, Annabelle, you could live for 40 more years... That 900 is like 700 once you account for taxes. So do we really want to spend half of it, 350, 400 grand, putting that into the dream house? I don’t see that working out.”
– Jill (20:23)
"Here’s how you can do your dream house. You want to know how? You’ve gotta sell your primary.”
– Jill (20:22)
5. Key Takeaways & Final Advice (22:39–23:12)
- Annabelle and her spouse have strong fundamentals: two pensions, two eventual Social Security checks, a sizable (if not unlimited) pre-tax retirement fund, and an affordable mortgage.
- A moderate splurge (Sequoia) is doable with planning, but a second home would unnecessarily compromise their financial security unless offset by downsizing their primary residence.
- Renting in target areas is a strategic and emotionally wise alternative.
Quote:
"I think that doing the second home, I’m okay. You had me at the $80,000 Toyota... But the $800,000 house—I just don’t think you could have something like $2.3 million of your net worth tied up in two illiquid assets."
– Jill (21:16)
"Renting’s okay. I think it’s a really good option for people who want to try something out."
– Jill (23:12)
Memorable Moments & Notable Quotes
-
On Retirement Flexibility:
"You guys are going to live a great, happy retirement. If things change... give us a holler and we’ll figure out the dream house."
– Jill (22:49) -
On the Hard Truth:
"Mark, dream crusher today. They don’t always work out, but it’s good to have them."
– Jill (23:12)
Important Timestamps
- 03:23 – Annabelle introduces her retirement planning questions
- 04:37 – Income, retirement savings, and job status breakdown
- 05:57 – Pensions, COLA, and retirement income sources
- 06:19 – Spending needs and health insurance gap identified
- 09:26 – Assets outside retirement, including home value and savings
- 11:06 – Part-time work discussion and its role in the plan
- 13:41 – Jill’s recommended withdrawal strategy
- 13:45 – Car purchase goal revealed
- 16:02 – Advice to beef up brokerage/savings for purchase
- 17:04 – Second/vacation home idea introduced
- 20:22 – Jill’s tough love: vacation home not feasible unless replacing primary
- 22:39 – Final affirmation and encouragement for the couple
Summary
This episode provides a thorough case study in practical financial planning for late-career couples with stable incomes but big dreams. Jill balances affirmation (“you’re in good shape”) with accountability, vetoing risky moves in favor of preserving flexibility, security, and future freedom. While Annabelle and her spouse can enjoy a well-earned, secure retirement and even upgrade their car, the allure of the “dream” vacation home simply doesn’t stack up against their long-term well-being unless their life circumstances (and housing situation) change. Renting remains a smart and liberating alternative.
Listeners with similar aspirations will find actionable guidance on how to weigh wants versus needs and keep their retirement dreams attainable and stress-free.