Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Retirement and College Expenses
Date: November 14, 2025
Host: Jill Schlesinger, CFP®
Main Theme: Navigating Retirement and College Savings — Balancing 529 Plans, Retirement Accounts, and Cash Flow

Overview

In this episode, Jill Schlesinger tackles the complex—and often stressful—financial scenario of balancing college funding for children with retirement security. A listener, Jen from the Mid-Atlantic, calls in for advice as she and her husband approach retirement and send twins to college. The discussion produces actionable strategies for handling 529 allocations, retirement withdrawals, pension considerations, budgeting, and the emotional complexity of large financial decisions. Jill and producer Mark break down solutions step-by-step, dissecting the math, timing, and feelings involved.

Key Discussion Points and Insights

1. Listener Situation: Jen’s Background (04:10 – 09:45)

• Jen (57, retired) and her husband (55, working, earns $360k salary + $175k bonus) are parents to twins, juniors in high school.
• Substantial 529 savings ($175k–$180k per child) but anticipating higher total costs (private school: $80k–$90k/year; out-of-state public: $70k–$75k/year).
• Assets include significant retirement savings (Jen: $1.5M traditional, $40k Roth, $36k Rule-of-55 401k; Husband: $2M 401k, $330k Roth, $55k IRA, growing $457f, $60k/yr), $50k in cash, and a $2M home ($925k mortgage at 2.75%).
• No significant pensions except for husband’s small one ($33k/year, no COLA), both eligible for Social Security.

2. College Funding vs Retirement Security (12:00 – 20:53)

• Jill and Mark analyze whether dipping into retirement assets for college will endanger future lifestyle goals, especially as current spending is about $23k/month.
• Asset Allocation for 529s:
  Jill strongly recommends moving the first year’s tuition in each 529 into stable value or money market funds to guarantee liquidity and avoid last-minute market crashes.
  • Quote (Jill, 19:28):
    “I would take the first year of tuition... and have it in the money market or whatever fixed income fund they have. 18 months is a long time and a short time, but if the market craps out... you’re going to be pissed if you don’t have that cash on hand for year one.”
• Mark suggests adjusting the husband’s 401(k) contributions—lowering them to the required 6% match to boost cash flow for education costs, while still benefiting from the employer’s generous additional flat contributions.
• Jen wonders if she should start tapping retirement funds; Jill reassures her to avoid large, lump-sum withdrawals. Instead, pursue a methodical, as-needed approach.
  • Quote (Jill, 17:52):
    "You can pull down money as you need it, but you don’t make these big sweeping changes. You should be okay."

3. Calculating Retirement Feasibility (16:51 – 18:56)

• Mark analyzes if current and future assets can support projected lifestyle (including college expenses) assuming husband works to 62. With ongoing employer matches, a pension, and future Social Security, they're on track.
  • Quote (Mark, 17:28):
    “Based on their current assets... in seven years, that’s going to be able to generate almost $20,000 a year, plus he’s got that $3,000 a month pension plus Social Security down the line.”
• Moving out and downsizing later (age 75–80) could free up more options, but no need to factor that in now.

4. Practical Action Items (18:56 – 21:05)

• Move first-year 529 tuition to cash/stable value soon.
• Temporarily adjust husband’s retirement contribution strategy to maximize cash flow without forfeiting employer support.
• Build more up in basic savings (beyond $50k current), which may aid college or buffer the household.
• Keep evaluating cash flow, especially as kids go to college and spending patterns shift.
• Update estate documents and ensure life insurance coverage is sufficient, given household dependence on husband’s income.
  • Quote (Jill, 20:53):
    “With his extra cash flow, you should be able to do it.”

5. Emotional Realities and Listener Reassurance (21:13 – 22:11)

• Jill addresses the emotional aspect for high earners—making big decisions is stressful at any income; it’s not just about math.
  • Quote (Jill, 22:11):
    “We’re all emotional beings, okay? That’s why this show exists. If this was all just a math equation, nobody would need you and me to walk through it with them.”
• Reinforces that financial planning is about timing, psychology, and personal values as much as dollars and cents.

Notable Quotes & Memorable Moments

• On the shock of college costs:
  Jill (06:35):
  “It is really incredible... I know that I’m being like an old stir when I say, like, wow, $350 grand for college—It’s a big number. It really is.”

• Advising incremental, not drastic, retirement withdrawals:
  Jill (17:52):
  “You can pull down money as you need it, but you don’t make these big sweeping changes. You should be okay.”

• On funding strategy and emotion:
  Jill (22:11):
  “We’re all emotional beings, okay? That’s why this show exists. If this was all just a math equation, nobody would need you and me to walk through it with them.”

Timestamps for Important Segments

• [04:10-09:45] — Jen explains her financial background and college savings.
• [12:00-15:27] — Jill and Mark assess the risk and security of using retirement funds for education.
• [16:51-18:56] — 401(k) funding strategy and projecting retirement feasibility.
• [18:56-20:53] — Specific recommendations for 529 allocations and contribution adjustments.
• [21:05-22:11] — Estate planning and emotional factors in financial decision-making.

Tone and Closing Thoughts

The episode is warm, practical, and supportive—Jill and Mark balance tough financial calculations with compassion and humor. Their guidance is methodical but adaptable to listener comfort. Jill emphasizes, for all income levels, that financial planning is both numbers and psychology, assuring listeners they’re not alone in the emotional weight of these decisions.

For more episodes or to submit your own financial question, visit JillOnMoney.com.