Podcast Summary: Jill on Money – "Student Loan Payment Strategy"

Host: Jill Schlesinger, CFP®
Guest: Logan from Missouri (Listener call-in)
Date: September 22, 2025
Platform: Audacy
Main Theme: Navigating the current uncertainty with student loan repayment strategies, especially for those close to potential loan forgiveness.

Episode Overview

In this episode, Jill Schlesinger takes a listener call from Logan, a 47-year-old from Missouri, who is grappling with a major student loan burden while making up for a late start in retirement savings. With the recent rollback of several student loan repayment programs and ongoing legislative changes, Jill walks Logan through his possible strategies as he nears the milestone of loan forgiveness. The conversation underscores the confusion and frustration many face in the current student loan landscape, as well as practical, actionable tips on building financial resilience.

Key Discussion Points & Insights

1. Logan's Financial Snapshot

• Age: 47
• Status: Partnered (finances semi-separate, jointly budget household expenses)
• Home: Jointly owned, worth ~$350k, over half paid off
• Mortgage: Estimated 3% interest rate (refinanced, originally partner’s purchase)
• Income: $104,000/year (full-time), plus $24,000/year VA disability
• Retirement Savings: $60,000 in a Roth 401(k), contributing 15% after a late start
• Other Savings: $8,000 in savings, $6,000 in checking (with intention to build emergency fund)
• Student Loan Debt: $98,000 (primarily graduate school), 15 years of on-time payments

2. Student Loan Repayment Dilemma

• The Biden-era repayment plan Logan relied on has ended.
• Remaining federal repayment programs are uncertain; likely to be reduced to 2-3 basic plans: standard and income-based.
• Currently, Logan’s repayment (due to COVID-era moratoria and disability income exclusion) is set at $0 until August next year.
• Logan is uncertain about his future payment amount and whether to pay aggressively now or continue making minimum payments until reaching the 20-year forgiveness mark.

Jill (07:10): "I'm inclined not to pay it all off. That's so unlike me because I like certitude... but... you can take that 24 grand a year of disability and sock it away and create kind of a sinking fund so that if you had to..."

3. Actionable Strategies Suggested by Jill

a. Emergency Fund First

• Build up an emergency savings fund to at least $30,000 (half a year’s spending).
• Do not invest savings in a Roth IRA yet—liquidity and easy access are more important.

b. Where to Save

• Keep funds in high-yield savings or CDs for accessibility and small gains.
• Credit unions may offer attractive rates; consider online banks as well.

Jill (09:02): "I would like you to have access just in case. Right. That's what Emergency reserve is."

c. Disability Income Management

• Continue saving the VA disability income as a “sinking fund” to prepare for possible lump-sum payments or unanticipated student loan costs.

d. When to Revisit the Student Loan Issue

• A crucial decision point will come when repayment resumes and actual payment amounts become clear.
• If it turns out to be unaffordable or forgiveness looks likely, strategies may change.
• Jill advises, “Touch base with us in a year when you know the payment amount.”

Jill (12:01): "That's going to be your next decision point... let's see what it comes back with. You know, we don't know."

4. Student Loan Forgiveness: Take the Wait-and-See Approach

• Logan is about five years away from possible 20-year forgiveness.
• Rather than paying off aggressively right now and forgoing the possibility of loan cancellation, build flexibility via savings, wait for regulatory clarity, and keep all options open.

Jill (13:52): "I'm just gonna go Zen with you, man. Five more years."
Logan (13:54): "I know. It's so close."
Jill: "It's so close. And so much can change, as we've just seen over the past five years, when it comes to student loans."

5. Estate Planning for Unmarried Couples

• Jill reminds Logan that, as an unmarried partner, state law can complicate inheritance and property ownership after death.
• She urges both partners to have basic estate documents: wills, power of attorney, and healthcare proxy.

Jill (13:12): "You should do that. You know what? You're a grown up now. Now you have to do it, I'm sorry to say."

Notable Quotes & Moments

• On the ever-changing student loan landscape:

Jill (12:24): “This is insane—this is insane to switch policies like this midstream on people. It really is. So I'm sorry you have to go through that.”

• About managing anxiety with uncertainty:

Jill (11:36): “If you, you know, if you have the wherewithal to just be able to carry this emotionally, I think you're going to be fine. And even if not, we will be able to figure out a plan before then.”

• On planning for emergencies:

Jill (08:19): “You need to have access to your money. You really do. So I think that until you get to this $30,000 savings level, I wouldn't put the money in a Roth. I just would like you to have access just in case. Right?”

Important Timestamps

• [02:40] Logan outlines his main concerns: high student loan debt and late retirement savings
• [06:03] Logan explains current student loan status and uncertainty about future payments
• [07:10] Jill details her pros/cons for paying off loans now versus waiting for possible forgiveness
• [08:43] Conversation shifts to emergency savings targets and how to structure accounts
• [12:01] Jill identifies the next big decision point: reassess plan when repayment resumes
• [13:07] Estate planning reminders for unmarried partners

Takeaways for Listeners

• When facing student loan uncertainty, maintaining cash flexibility and optionality is key; don’t rush to pay off if forgiveness is possible.
• Build a robust cash reserve before focusing on tax-advantaged or higher-yield investments, especially if large future expenses are unpredictable.
• Estate planning is crucial for unmarried couples who jointly own assets.
• Keep lines of communication open with experts—financial plans may need to pivot as policies change.

If you have a similar financial dilemma or want guidance, go to jillonmoney.com, click the 'Contact Us' button, and you could be the next caller featured!