How to Money - Episode #1060: Ask HTM - Open Enrollment Entanglements, Worthwhile BNPL Scenarios, & Continuing to Invest with Outstanding Debt

Release Date: November 10, 2025
Hosts: Joel and Matt
Podcast: iHeartPodcasts

Episode Overview

In this upbeat and practical Ask HTM episode, Joel and Matt answer listener questions at the heart of everyday personal finance: navigating open enrollment for health insurance, whether buy now pay later (BNPL) services ever make sense, and balancing investing while paying down debt. As always, the duo brings empathy, humor, and honest, jargon-free insight, sharing real numbers and personal stories to help listeners make sound financial decisions.

Key Discussion Points & Insights

1. Open Enrollment: Should You Switch Health Plans?

Listener Question: Brian from Chicago asks how to weigh switching health insurance providers during open enrollment to save $1,200, considering doctor networks and prescription coverage.

Guidance & Insights:

• The High Cost of Health Insurance

  • Average annual cost for a family: $27,000
  • Employer covers $20,000, employee covers ~$6,000, plus other costs ([11:05])
  • "Even with great workplace coverage here, we're talking...you could easily spend over $10,000, maybe closer to $15,000 on health care costs in a given year between just like the premiums and then just some of the other costs that go into it." – Matt ([11:25])

• Evaluating Your Options

  • Compare total annual cost: premiums, deductibles, copays, out-of-pocket max
  • Use last year's expenses as a guide, plus any planned procedures ([12:38])
  • Don't overlook the headache of changing providers: loss of preferred doctors can outweigh cost savings for some families ([14:09])
  • "If you have to go and find a new pediatrician...that might be a massive headache. That being said, extreme times call for extreme measures." – Matt ([14:24])

• Prescriptions

  • Factor in prescription costs under each plan
  • Consider cost-saving sites for generics: Cost Plus Drugs, GoodRx ([15:34])

• HSAs (Health Savings Accounts)

  • Benefits: tax-advantaged, grows for the future, sometimes employer match
  • Only pursue if a high-deductible plan actually makes sense ([16:02])

• Health Sharing Plans (Alternative Option)

  • Can dramatically lower costs (example: $2,500/month on exchange vs. $374/month health share for family of 6) ([17:41])
  • Less suitable if employer’s plan is well-subsidized; best for self-employed or those without coverage ([18:52])
  • "Not all are religious or faith-based, either—Sedera is a great option...where there’s a whole lot of folks who are served well via that organization." – Matt ([18:46])

• Bottom Line:

  • Weigh both math and lifestyle: "It's partly math, but it's partly lifestyle and what you care about when it comes to your healthcare coverage." – Joel ([19:57])

2. Buy Now, Pay Later (BNPL): Worth It for Big Discounts?

Listener Question: Wayne from Philadelphia asks if Matt and Joel would ever consider BNPL if it meant a meaningful discount (10%, 20%, even 80%).

Guidance & Insights:

• General View on BNPL:

  • The hosts generally dislike BNPL as it can encourage overspending and offers little consumer protection ([24:53])
  • "The only thing that Buy Now Pay Later offers...is you get to pay that item off over a longer period of time. And so what that leads to for some people...is poor behavioral and financial results, which have been well documented." – Joel ([28:41])

• Discount Exception:

  • If the discount is significant, their position changes:
    • Joel: "If there was like a 10 or 20% off perk for using Buy Now Pay Later, I’d probably use it a lot more." ([25:46])
    • Matt: "I would do it for like 5% off...I would get in there, I’d figure out how to incorporate that into my financial system." ([27:42])
    • Both stipulate: only if they wasn’t going into debt, i.e., always paying immediately ([25:48], [27:43])

• Why Credit Cards Are Still Preferred:

  • Offer cash back, buyer protections, credit score benefits ([28:20])
  • BNPL only offers delayed payment, which often leads to more spending ([28:41])

• On Friction & Behavioral Traps:

  • Both discuss how frictionless payments (in BNPL or contactless cards) can make overspending easier ([30:10])
  • "The whole way they're designed is essentially to get people to spend in ways they otherwise wouldn't, to become even more of a consumer." – Joel ([32:46])

Memorable Quote:

“If you don’t have the cash on hand, you need to have the cash on hand if you are going to use these methods of payment...we’re trying to raise the standard here, we’re trying to raise the bar. The cash on hand, that is your license to be able to play this game.” – Matt ([26:56])

3. Investing While in Debt: Should I Pause Retirement Savings to Pay Down Debt?

Listener Question: Kelsey from Colorado Springs wonders if she should pause 401k/Roth IRA investing to pay down $25,000 in high-interest debt (18%), given she has $90k in her Roth IRA and $8k savings.

Guidance & Insights:

• Acknowledging Both Sides

  • Kelsey is commended for significant IRA savings, but "if you do both those things, stop contributing to your Roth, contribute less to your 401k, only up to the match. That allows you to claw back more cash flow to work towards debt payoff a heck of a lot more quickly." – Joel ([38:33])
  • Matt shares his own story of making the same mistake: investing before building a cash cushion ([36:03])

• Money Gears Approach:

  • Gear 1: Savings,
  • Gear 2: 401k match,
  • Gear 3: Pay off high-interest debt (~10%+)
  • "After that, that’s when you can resume investing for your future. And you’ll have even more money for that purpose with less debt lingering in your life." – Joel ([39:05])

• Why Not to Pull from Roth:

  • Roth contributions are accessible but don’t draw down unless absolutely necessary — you’ll interrupt compounding and can't put dollars back due to contribution limits ([41:54])

• Debt Payoff Priority:

  • Double-digit debt beats stock market investments for ROI and peace of mind ([37:54], [40:36])

Memorable Quote:

“Credit card debt...It is a big problem and there aren’t many better things you could be doing with your money than paying that debt down as quickly as possible.” – Joel ([41:22])

4. Facebook QOTW: Will Paying Off My Mortgage Hurt My Credit Score?

Listener Question: If I pay off my mortgage (no other loans, only active credit card), will it hurt my score if I want to buy real estate in 2 years?

Guidance & Insights:

• Yes, paying off your mortgage can cause a dip in your credit score, especially if it’s your oldest account and only installment loan ([48:39])
• Credit mix and length of credit history matter; losing an installment loan dings your score ([49:05])
• The effect is temporary and relatively minor if your score is already strong ([51:18])
• “If you have a really high credit score to begin with, it doesn’t matter, you’re still going to be able to qualify for the best rates and terms.” – Joel ([51:28])
• Instead of rushing, weigh opportunity cost: can you invest or save that money at a better rate than your (likely-low) mortgage? Better options may be available ([50:23])

5. Facebook QOTW: What’s in the 15% Savings Rate?

Listener Question: Does the recommended 15% savings rate include my 401k contributions?

Guidance & Insights:

• Yes. The 15% should be based on your gross income and absolutely includes 401(k), Roth, even debt payoff ([52:19])
• Don’t stress obsessively over the specifics—consistency is most important ([53:00], [53:39])
• Matt: “As long as you are consistent with like, however it is you are calculating your savings rate over time. As long as you stick with that, I think that’s the biggest thing, especially if early retirement is a goal of yours...” ([53:11])

Notable Quotes & Moments

• On Market Corrections:

“High prices are the cure for high prices. ... The opposite is true as well: low prices are also the cure for low prices.” – Matt & Joel jointly discussing economic cycles ([04:06–06:19])

• On Credit Cards vs. BNPL:

“If there’s a Buy Now, Pay Later that was willing to offer 5% off just across the board ... I would do it.” – Matt ([27:42])

• On Financial Habits:

“You learn the lessons with like, one or two zeros at the end of it, as opposed to like, three or four.” – Matt, on mistakes early in your investing life ([37:11])

Timestamps for Key Segments

| Timestamp | Topic / Quote | |------------|--------------------------------------------------------------------| | 09:51 | Open Enrollment: Comparing Health Plans (Brian’s Q) | | 13:28 | What’s Included in “Total Cost” for Health Insurance | | 17:40 | Health Sharing Plans: Matt’s Family Example | | 23:20 | Buy Now, Pay Later Discount Hypothetical (Wayne’s Q) | | 25:46 | Joel explains discount as exception for BNPL | | 36:03 | Matt’s “too early” investing story | | 37:54 | Debt payoff as top priority | | 41:54 | Warning: Don’t tap Roth IRAs for debt payoff if you can avoid it | | 47:29 | Mortgage payoff and credit score (Facebook QOTW) | | 52:10 | 15% savings rate includes 401k |

Closing Thoughts

Joel and Matt continue to embody clear, actionable, and honest financial advice. They remind listeners to be intentional: crunch the numbers, value your peace of mind, and use behavioral cues to your advantage. And as always, save with purpose, invest with a plan, and keep a sense of humor along the way.

Best Friends Out!