Jill on Money with Jill Schlesinger

Episode: Can We Stop Saving for College?
Date: March 11, 2026
Host: Jill Schlesinger, CFP®
Producer/Co-Host: Mark

Episode Overview

This episode of Jill on Money centers on complex and sometimes controversial personal finance questions from listeners—ranging from saving for college and retirement planning to Roth conversions and paying quarterly taxes as a gig worker. The heart of the episode (and the title’s focus) is a debate about when to stop saving for your child’s college education, but the episode also includes thoughtful answers about risk in retirement, the need for financial advisors, tax efficiency, and navigating taxes as a freelancer.

Key Discussion Points & Insights

1. Listener Mailbag: Financial Planning in Retirement

Timestamps: 02:41–05:40

• Steve, 77, and his spouse (76) have pensions and Social Security totaling $7,300/month take-home pay; they live on $6,000/month and save $1,000/month in their 70s.
• Assets: $300k laddered CDs, $100k in high-yield savings, $15k cash, no debt, grown children, living in a continuing care retirement community.
• Questions addressed:
  • Safe Investments: Jill affirms that in their case, avoiding risk is reasonable, and beyond CDs and high-yield savings, there are not really lower-risk vehicles that make sense.
    • "If you don’t want risk, take no risk." – Jill (03:36)
  • Tax Minimization: No major actions recommended; pensions and Social Security are taxed, and interest from bank products can’t really avoid taxes.
    • "You can’t make your pension go away. You can’t make your Social Security go away." – Jill (03:58)
  • Long-Term Care/Medicaid: Nothing to do at this stage; spend down assets as needed.
    • "I don’t think you got a lot to worry about."

2. Do You Need a Financial Advisor?

Timestamps: 05:41–06:41

• John asks if having under $400k in retirement accounts warrants hiring a financial advisor.
  • Jill: If it’s a simple situation (single account, not many complexities), probably not.
  • "If you have just one account and it’s a retirement account and you have $400,000, I’m not sure you do need an advisor..." – Jill (06:14)

3. The Big Topic: When to Stop Saving for College

Timestamps: 06:42–08:39

• Terry and spouse, with two young children (2 and 4), already have $158k and $135k saved in 529 plans respectively.
• Goal: Pay for in-state public university (currently $40k–$55k/year); comfortable with investment strategy.
• Question: With costs rising, can they ease up on saving?
• Mark: "I would probably ease up. I mean by the time each of these kids is 18, they’re going to have well over $300,000 each." (07:36)
• Jill: Suggests continuing for a couple more years if desired, then letting the account grow.
  • "But by the time that...four-year-old is in first grade, I don’t know, you probably can let this roll a little bit." (07:57)
• Investment risk shifting: Mark advises shifting to more conservative investments sooner, around age 12 rather than high school.
  • "Once those kids turn 12, that’s when I would start peeling off some of the risk." – Mark (08:29)
• Notable Quote:
  • "You can kind of ease up or...do it for a couple more years. But...at some point, let this roll a little bit."

4. Roth Contributions & Conversions at High Income

Timestamps: 08:40–13:47

• Ann, 54, California: Single mom, net worth ~$3M; high and rising income (AGI $350k → $770k, may reach $1M/year), spends $8k–$11k/month, substantial 401k and brokerage savings, and already using a backdoor Roth.
• Main question: Should she make Roth 401k contributions or in-plan conversions at her current high income level?
• Jill: Not right now—taxes are too high; wait until income falls (potentially in 2028 after child finishes college).
  • "I certainly wouldn’t do an in-plan conversion right now." – Jill (11:37)
• Mark: Would also wait until the tax bracket drops, but notes the power of tax-free growth.
  • "In terms of doing conversions, if she knows her income is going to go down in a few years, I would probably wait until then." – Mark (11:49)
• Jill: Suggests start Roth 401k or conversions once income drops, but not imperative—plan will need revision as circumstances unfold.
  • "I wouldn’t necessarily do [conversions] while I'm in my 50s, because who knows what this kid’s going to do...But this is quite a great problem to have, don’t you think?" (13:26)
  • Mark: "I'll say." (13:47)

5. Quarterly Taxes for Freelancers

Timestamps: 13:48–14:41

• Jasmine: Started a remote job paying her via PayPal; unsure if she needs to pay estimated quarterly taxes.
• Jill: Depends on whether withholding is happening elsewhere; filing current taxes will clarify requirements.
  • "You’ll make a decision based on this tax filing year...there’s no reason to do anything this second." (14:17)
• Mark: If nothing is withheld, start saving a percentage for quarterly payments based on your bracket.
  • "If nothing’s being withheld, then...you’re probably going to want to...put aside that percentage each month just to make those quarterly payments going forward." (14:28)
• Both stress: Quarterly tax payments are not difficult, don’t panic.

Notable Quotes & Memorable Moments

• "If you don’t want risk, take no risk." – Jill (03:36)
• "You can’t make your pension go away. You can’t make your Social Security go away." – Jill (03:58)
• "If you have just one account...and you have $400,000, I’m not sure you do need an advisor..." – Jill (06:14)
• "I would probably ease up. I mean by the time each of these kids is 18, they’re going to have well over $300,000 each." – Mark (07:36)
• "Once those kids turn 12, that’s when I would start peeling off some of the risk." – Mark (08:29)
• "I certainly wouldn’t do an in-plan conversion right now." – Jill (11:37)
• "I'll say." – Mark reacting to Ann’s “good problem to have” (13:47)

Timestamps for Key Segments

• Retirement Investing with Low Risk: 02:41–05:40
• Financial Advisors for Small Accounts: 05:41–06:41
• College Savings—When to Stop: 06:42–08:39
• Roth Contributions/Conversions Q&A: 08:40–13:47
• Quarterly Taxes for Remote/Gig Workers: 13:48–14:41

Summary

This episode provided clear, jargon-free advice for listeners navigating different financial crossroads. Jill and Mark’s discussion on college savings demystified how much is “enough,” reassuring high-saving parents that, after a point, continued contributions may be unnecessary. For listeners approaching retirement, the advice was refreshingly simple—if risk makes you uncomfortable, there’s no shame in sticking to cash or CDs. The episode also broke down complex issues like Roth conversions at high incomes and the practicalities of making estimated tax payments, all delivered in the supportive, practical tone that characterizes Jill on Money.

Listeners left with actionable, judgment-free guidance and a sense that even their “financial worries” are often signs of prudent, thoughtful planning.