NerdWallet’s Smart Money Podcast

Episode: Preparing Finances for Fall and How to Help Parents Who Haven’t Saved Enough
Date: September 22, 2025
Hosts: Sean Pyles, CFP® & Elizabeth Ayoola
Expert Guest: Kate Ashford

Episode Overview

In this practical and relatable episode, Sean and Elizabeth guide listeners through financial self-checks to prepare for fall and the end-of-year milestones, offering actionable questions to assess spending, saving, and readiness for both the holidays and the upcoming open enrollment season. The second half pivots to an in-depth Q&A session, responding to listener Steph’s concerns about supporting aging parents with limited retirement savings. Guest expert Kate Ashford joins the discussion, delivering compassionate, concrete advice for navigating sensitive family financial conversations, optimizing resources, and balancing self-preservation with generational care.

Key Discussion Points & Insights

1. Five Financial Questions to Prepare for Fall

(01:14 – 11:17)

Sean & Elizabeth’s “Autumn Audit”

• The hosts urge listeners to reflect on the year, evaluate their goals, and prepare for holiday and new-year transitions.
• Sean quips, “It being fall, that basically means the year is over. So Elizabeth, it's time to start working on your New Year's resolutions.” (01:24)
• Practical questions feature:
  • What to leave behind from summer, and what to take forward?
    • Sean: Scaling back discretionary expenses due to wedding costs, refocusing on rebuilding savings.
    • Elizabeth: “Goodbye summer, and all of the costs that it came with,” excited to cease paying large childcare bills and focus on boosting emergency savings. (02:38)
  • Affordable ways to indulge in fall activities without overspending.
    • Sean: “If you want to do all of the fall things like do the corn maze and go to the pumpkin patch and go to the haunted house, that stuff gets really expensive.” (03:38)
    • Elizabeth: Advocates for creative alternatives, such as growing your own pumpkins or adjusting holiday traditions.
  • Planning for open enrollment:
    • Sean recommends tracking current year healthcare spend as a baseline for 2026 choices, and highlights possible ACA premium increases.
    • Elizabeth: “Look out for a summary of benefits coverage so that you can see, you know, what your benefits are... and also your out-of-pocket maximums.” (06:28)
  • Retirement contribution check-in:
    • Sean provides IRA and 401(k) caps and deadlines; both hosts compare their annual performance and discuss asset allocations.
    • Elizabeth celebrates, “Mine is up around 16% year to date!” (08:10)
  • Holiday readiness:
    • Budgeting for gifts, designating savings for the holidays, and incorporating future goals to rein in spending.
    • Sean shares, “With my honeymoon coming up and my partner and I going to Japan and South Korea, I’m planning on having that be the place where I get all of my holiday gifts for everyone.” (09:39)
    • Tip: Track flight prices early for holiday travel and factor 2026 goals into end-of-year financial choices.

2. Money Question: Helping Parents Nearing Retirement with Insufficient Savings

(11:47 – 27:30)

Listener Q: How can I support my aging immigrant parents who haven’t saved enough for retirement, without jeopardizing my own finances?

A. Starting the Conversation: How to Talk to Your Parents about Money

• Kate Ashford recommends “disguising money and estate planning questions in the form of asking for advice from your parents,” or using headlines as conversation starters. (13:18)
  • Sample: “Hey mom, my spouse and I are working on our own estate planning and I’m wondering what you both have done with yours.”
• Elizabeth’s experience: “I have very old school or traditional parents who did not talk to me about money... So I just asked him straight up, like, do you have any life insurance? What would you like to do with your assets?” (14:17)
• Sean’s tip: Designate a single “money person” among siblings, but keep the whole family looped in.

B. Assessing Your Parents’ Financial Picture

• Topics to cover include:
  • Retirement income sources and expected Social Security (check/estimate via SSA.gov).
  • Housing situation (own/rent, mortgage paid off?).
  • Debt obligations.
  • Expected healthcare expenses.
  • “You want to understand... the scope of what you expect to get out of the first conversation and then map it out...” (16:55 Sean)

C. Self-Preservation: Prioritizing Your Own Financial Security

• Sean: “It’s like they say on airplanes, put on your mask before you help someone else with theirs.” (17:48)
• Checklist for helping:
  • Minimum emergency fund ($1,000–$2,000)
  • Resolve high-interest debt
  • Progress on retirement savings
  • Budget that accounts for any regular support to parents
  • Never borrow from your own 401(k) or retirement funds to help family

D. Ways to Support Aging Parents

• Supplement income or cover bills: Direct payments for specific expenses offer transparency and control.
  • Stat: “NerdWallet had a survey last year that found that for Americans who say they're helping their parents financially, 60% are paying for food, 41% are paying for housing costs, and 48% are paying for other things.” (19:16 Kate)
• Contributing to IRAs:
  • Allowed only if parents have earned income equal to the contribution.
  • 2025 Contribution limits: up to $8,000 for those 50+.
• Consider multigenerational living: Can offer mutual support if the logistics and relationships work.

E. Housing Solutions

• If Social Security is the only source, consider subsidized senior housing or moving to lower cost-of-living areas; get on waitlists early due to long processing times.
  • “Your local Area Agency on Aging may have information on public or subsidized housing options... and any other supports that might help, like property tax breaks, for instance.” (21:03 Kate)
• Downsizing or state-to-state moves may open options, but be mindful of family members’ preferences.
  • Elizabeth: “My dad is a die hard Florida fan. He does not want to leave Florida.” (21:59)

F. Encouraging Parents’ Self-Help

• Cut expenses, explore part-time or seasonal work, sell crafts/services.
• Pay down high-interest debt; maximize returns on any savings (high-yield accounts).
  • Kate: “To the extent that they can cut back or earn more money, every little bit is going to help.” (22:58)

G. Tax Considerations and Government Benefits

• Claiming parents as dependents is rare: Must provide majority support and parent’s income must be very low (approx. $5,000 or less).
  • “You have to provide more than half of their support... and the parents would have to be very limited in their income.” (23:43 Sean)
• Explore:
  • Property tax breaks
  • Utility assistance programs
  • SNAP and other food benefits
  • Local agencies on aging
  • Resource: "USA.gov is also a good place to look." (24:13 Kate)

H. Navigating Medicare & Medicaid

• Two choices at age 65:
  • Original Medicare (government-managed; supplement plans provide flexibility and broader coverage, but are costly)
  • Medicare Advantage (private; lower/no premiums, may include dental/vision but restrictive networks)
  • Kate: “For the most flexibility and risk management, original Medicare with a Medicare supplement plan is kind of the way to go... But if you can't afford a supplement plan, then Medicare Advantage may be the better option...” (25:00)
• Further help: State Health Insurance Assistance Programs (SHIPs) offer free guidance.
  • Find them at shiphelp.org
• At very low incomes, layering Medicaid over Medicare can reduce medical costs even more. Check medicaid.gov.

I. Big Picture Advice and Emotional Encouragement

• “Navigating retirement for parents who haven't saved much is stressful. But kudos to Steph for seeing this coming and trying to take proactive steps... It’s much easier to get information and make decisions now before anyone is in any kind of crisis. So yay for thinking about this early.” (27:12 Kate)

Notable Quotes & Memorable Moments

• Sean, on adjusting for fall:
  “I'm leaving behind all non discretionary expenses because it turns out that my wedding expenses are growing by the day and I'm currently way over budget…” (01:51)
• Elizabeth, on holiday budgeting:
  “What's interesting, actually, as I'm thinking about my budget is I wasn't joking when I said I've started doing my goals for 2026. So I've been looking at how much I want to save for next year, and that's helping me rein in my spending, especially as I tend to overspend during the holidays.” (09:00)
• Kate Ashford, on easing into difficult talks:
  “These conversations can feel really awkward, but they're also so important. I recommend people disguise money and estate planning questions in the form of asking for advice from your parents…” (13:18)
• Sean, on family financial roles:
  “It can be helpful if you have siblings to maybe designate one person as the one who's maybe the go to for that. But make sure you're all in the loop on what's happening with your parents.” (15:14)
• Elizabeth, on parents and housing independence:
  “My dad is a die hard Florida fan. He does not want to leave Florida… He's an adult at the end of the day. So if he wants to stay in Florida, well, what can we do?” (21:59)

Timestamps for Key Segments

• 01:14 – Season transition: Reviewing and setting new financial goals
• 03:38 – Affordable ways to enjoy fall festivities
• 06:09 – Healthcare: Preparing for open enrollment
• 07:30 – Year-end retirement account and 401(k) checkup
• 09:00 – Holiday planning and tips for smart spending
• 11:47 – Listener email: Supporting parents with little retirement savings; segment introduction
• 13:00 – Kate Ashford joins; initiating financial talks with parents
• 15:52 – What financial topics to discuss with aging parents
• 17:27 – Protecting your own finances first
• 19:16 – Approaches to financially supporting parents & multigenerational living
• 21:03 – Housing support options and resources
• 22:58 – Cutting costs, increasing income, and making the most of savings
• 23:43 – Tax benefits & government aid possibilities
• 25:00 – Navigating Medicare, Medicare Advantage, and other healthcare programs
• 27:12 – Closing encouragement for listeners in similar situations

Resources Mentioned

• SSA.gov – For Social Security estimates
• SHIPHelp.org – State Health Insurance Assistance Programs
• USA.gov – Government benefits portal
• Medicaid.gov – Medicaid eligibility and enrollment
• NerdWallet's Best High-Yield Savings Accounts – Up-to-date rates

Tone & Style

Conversational, practical, empathetic, research-driven—emphasizing supportive strategies, clear explanations, and actionable steps for listeners seeking to take control of their finances and navigate family responsibilities.

For Listeners Who Haven’t Tuned In

This episode blends seasonal financial maintenance—think budgeting, benefits, and holiday planning—with deeper advice for those supporting family members facing financial instability in later life. If your parents are approaching retirement with little saved, or you simply want a strategic fall tune-up for your finances, the Nerds break down what to do and how, with compassion, experience, and a whole lot of actionable advice.