Podcast Summary: Jill on Money with Jill Schlesinger

Episode: Can I Retire Before Kids Are Done With College?
Date: February 4, 2026
Host: Jill Schlesinger, with producer Mark

Overview

This episode features host Jill Schlesinger, CFP®, and producer Mark, fielding listener questions centered around early retirement planning, saving for college while supporting a family, optimizing retirement account contributions, and strategic approaches to funding higher education. The podcast, known for its jargon-free advice, addresses the feasibility of stepping back from work before all children have completed college, explores Roth and traditional IRA strategies, and weighs options for covering college expenses without derailing retirement security.

Key Discussion Points & Insights

1. Listener Brian's Early Retirement & College Planning Dilemma

Segment Start: [02:20]

Background

Brian, 49, married, with three kids (ages 16, 13, and 9), a sole earner in New England, wants to retire around age 56. He wonders if he can afford to sell his business (valued at $800k), help his kids with college, and live on $10k–$12k per month, possibly with part-time work.

Financial Snapshot

• Salary: $175,000/year; 20% ownership in small business
• Retirement Savings:
  • $850k in 401(k)/IRAs
  • $250k brokerage
  • $264k in a defined benefit (cash balance) plan
  • $60k Roth
  • $136k earnings in the business
  • Business value (his share): $800k
• Real Estate: $600k home, $200k mortgage
• Cash: $120k
• 529 College Funds: $103k total
• Desired Retirement Age: 56 (when his oldest finishes college, middle has 2 years left, youngest 3 years until college start)
• Monthly Spending Goal: $10,000 (Jill: “let’s make that $12k for planning”)
• Healthcare: Would use ACA exchange unless part-time work provides coverage
• Spouse: Stay-at-home mom; open to part-time work

Jill & Mark’s Analysis

• Mark:

  “Very, very close. Probably too close for comfort.... At 56, very close—but if they’re both willing to work part time, they could figure out a way to make it happen.” [08:52]

• Jill:

  “A lot of the money you have is going to be taxed. So even when you hear $4 million from Mark, like that’s pre-tax. We gotta pay tax on that; that’s not actually enough money.” [09:16]
  “Would you rather work... and kind of stretch it into another couple of years... so be full-time till 58, 59, or would you rather call it quits and really put the pressure on yourselves to come up with some part-time income that will cover most of the $12k a month you need?”
  “Your wife hasn’t worked in 15 years. Is it going to be so easy for her to just go get a job? I don’t know. Maybe. But maybe not.” [09:16]

Key Takeaway

• Brian is close to being able to retire at 56, but it’s risky given the tax hit, need for part-time income, rising healthcare costs, and children’s education bills. Stretching full-time work a few more years might offer safer financial footing and reduced pressure.

2. Retiring Early with Lean Expenses: Listener Don

Segment Start: [10:41]

Background

Don, 43, single, self-employed, invests $80k–$100k yearly, low spending, holds a 2.75% mortgage, and about $1.1 million in investments (stocks, ETFs, crypto, cash). Wants to retire within five years.

Jill & Mark’s Analysis

• Mark:

  “I’m guessing he spends very, very little, and that’s really the only way it’s going to work for him.” [11:50]

• Jill:

  “I want to know what your expenses are, and then whether you would work part time... We’re going to call this episode Pipe Dreams and Real Dreams or something like that.” [11:55]

Key Takeaway

• Retiring early on a moderate portfolio is possible only with minimal spending or additional part-time income. Knowing exact expenses is crucial.

3. Roth vs. Traditional IRA Contributions for High Earners

Segment Start: [12:44]

Background

Clint and his wife exceed Roth IRA contribution limits. He asks if he can contribute to a traditional IRA on top of his 401(k), and how to navigate Roth/backdoor options.

Jill & Mark’s Advice

• Jill:

  “You can do what is called a backdoor Roth... only if there is not another IRA account that's out there.” [13:45]
  “Don’t do the traditional IRA. You’ve got a bunch of money that's already in the traditional asset, the 401(k). Let's get you to Roth.” [13:59]

• Mark:

  “You can [contribute to both], but I wouldn't. I really see no reason anymore to use a traditional IRA.” [14:08]

  “If you're looking to get Roth money, check if your 401(k) has a Roth option.” [14:15]

Key Takeaway

• For high earners, prefer backdoor Roth IRA strategies and maximizing Roth 401(k) over additional traditional IRA contributions, unless specific tax reasons apply.

4. Switching to Roth TSP & Considering Roth Conversions (Federal Employees)

Segment Start: [14:53]

Background

N. and her husband (both with federal TSP accounts) ask whether to switch all new contributions to Roth and if they should begin Roth conversions to avoid a future tax “cliff” from RMDs.

Jill & Mark’s Advice

• Jill:

  “Absolutely, positively going into the Roth... I don’t know about the conversions.... It would be great to convert some of the money, but I don’t know if they have the assets to pay for it.” [15:46]

• Mark:

  “It's definitely appealing if they can pull it off and have the assets to pay the tax bill. But as far as switching over to Roth, 100%. Your husband's 51. If he's going to be working for a few more years, there's no reason to do any more pre-tax.” [15:57]

Key Takeaway

• Federal workers likely to have strong pensions should shift new contributions to Roth TSP; future Roth conversions depend on ability to pay the tax bill from non-retirement funds.

5. Best Ways to Fund College: 401(k) Loans, HELOC, or Reduce Retirement Savings?

Segment Start: [16:11]

Background

Sarah and her husband, both in their early 50s, face steep costs to finish funding their child’s prestigious college education, seeking optimal ways to raise $150k after 529 funds run out.

Jill & Mark’s Advice

• Mark:

  “I would pause your retirement contributions for two years... just up to the match, put that money towards college, and probably take out what will end up being a pretty manageable loan for the rest.” [17:20]

• Jill:

  “Even if you just have to keep [new contributions] in a money market so it doesn’t have to be taxed... keep pumping that up... That is the best place to put that money.” [17:51]
  “You don’t have to go into super duper debt to get your kids where they need to go or where you would like them to go.”

Key Takeaway

• Do not raid retirement accounts (via loans) or over-leverage your home unless absolutely necessary. Instead, pause or reduce retirement contributions (down to match), divert those funds to immediate college bills, then use manageable educational loans for the balance.

Notable Quotes & Memorable Moments

• On Early Retirement While Funding College:
  “A lot of the money you have is going to be taxed... That’s not actually enough money.” – Jill [09:16]

• On Making the Numbers Work:
  “Very, very close. Probably too close for comfort... if they’re both willing to work part time, they could figure out a way to make it happen.” – Mark [08:52]

• On Traditional IRAs for High Earners:
  “I really see no reason anymore to use a traditional IRA.” – Mark [14:08]

• On Using Retirement Assets for College:
  “You don’t have to go into super duper debt to get your kids where they need to go...” – Jill [17:51]

Timestamps for Major Segments

• [02:20] – Brian’s question: retiring at 56 and college expenses
• [08:52] – Mark: “Very, very close. Probably too close for comfort.”
• [09:16] – Jill’s detailed advice on the pre-tax nature of savings
• [10:41] – Don’s early retirement and lean living
• [12:44] – Roth and traditional IRA rules for high earners
• [14:53] – Roth TSP and Roth conversions (government employees)
• [16:11] – Funding college: 401(k) loans, HELOC, or other strategies
• [17:20] – Mark’s advice on pausing retirement contributions
• [17:51] – Jill: “You don’t have to go into super duper debt...”

Summary

This episode delivers practical, direct advice for those eyeing early retirement, especially while supporting children through college. Jill and Mark stress the importance of realism in drawing down assets early, caution against overreliance on pre-tax savings, and recommend maximizing Roth options and adjusting contributions in response to family needs. For college funding, they advocate using current income over loans from retirement assets. Their approach, while conservative, emphasizes sustainability, flexibility, and long-term security—hallmarks of the “Jill on Money” ethos.

For further personalized questions, listeners are encouraged to visit jillonmoney.com and use the ‘Contact Us’ form.