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- Oct 22, 2025
Oct 22, 2025
This Week’s Money Map:
🚨 2025–26 open enrollment season survival guide
🚘 Car insurance playbook: Proven ways to save more
🌴 How to find the cheapest travel insurance for your holiday trip
✈️ Unlock the BOGO travel hack: 120K points + the Companion Pass with Southwest!
🚨 Your 2025–25 open enrollment survival guide
It’s the end of October, and open enrollment is about to hit like a freight train. Between November 1, 2025 and January 15, 2026, you can review, change, or enroll in a health insurance plan for 2026. Miss the window and you’re stuck with whatever coverage (or lack thereof) you’ve got, no matter how much your premiums spike.
Why this year’s open enrollment really matters
Premiums, deductibles, and drug prices are all rising; employers are trimming benefits; and Medicare’s tweaking coverage options again. Translation? The plan that worked for you last year might dent your wallet in 2026.
On top of all that, ACA subsidies are set to expire at the end of 2025 unless Congress acts now to extend them. Folks are already seeing their 2026 premium quotes double or even triple without these ACA premium cuts. That’s why reviewing your plan now isn’t optional, it’s survival.
Your open-enrollment checklist
Do this before Halloween:
Mark your calendar — twice
ACA Marketplace and individual plans: November 1st – January 15th. Medicare: October 15th – December 7th. If you miss these, you’ll need a qualifying life event (marriage, new baby, job change) to enroll later.Log into your account now
Healthcare.gov, your employer portal, or your Medicare dashboard, whatever applies. Confirm your info, dependents, and income details. Wrong numbers = wrong subsidies = higher premiums.DON’T let it auto-renew
Don’t assume “same plan” means “same cost.” Many 2026 plans are hiking rates or changing provider networks. Check the following:Monthly premium (your regular payment)
Deductible (what you pay before insurance kicks in)
Out-of-pocket max (your worst-case scenario)
Covered doctors and meds (networks could shift every year)
Estimate your 2026 health needs
New prescriptions? A planned surgery? A baby on the way? Pick a plan that fits next year’s life, not last year’s.Compare plans!
Sites like Healthcare.gov, Medicare.gov, and MoneyGeek’s free health insurance calculator can run side-by-side comparisons in minutes. They’ll show your estimated annual costs — not just the shiny low premium.Double-check your subsidy or employer credit
Many people leave money on the table. Even a small income change can alter your tax credit. A five-minute update could drop your premium by $50–150 a month.Don’t forget about Medicare
If you’re over 65, your open enrollment is already live (Oct 15–Dec 7). Compare your Part D drug plan — premiums and formularies change yearly. Many seniors overpay simply because they never switch. Check the Medicare Plan Finder and lock in a cheaper option before the deadline.
Act now, save big later
Open enrollment isn’t exciting, but it could be the biggest money move you’ll make this year. Spending an hour now could save you hundreds or thousands in 2026. Click, compare, and lock in your coverage before the holidays steal your attention — and your cash…
🚘 The new car insurance playbook: Proven ways to save more
If your 2025 car insurance renewal made your jaw drop, you’re not imagining it. Average premiums jumped this year across the country. Blame it on tariffs, pricier cars, record repair costs, and more extreme weather-related event claims.
But while everyone’s complaining, some drivers are quietly slashing their rates by hundreds, simply by playing the insurance game differently. Here’s their rulebook:
Rule #1: Never auto-renew without checking
Auto-renewal is convenient, which is exactly why insurers count on you not noticing that your premium just climbed 15%. A 10-minute check could save you $500–1,000 a year. Before your policy renews, always:
Get at least three fresh quotes (from GEICO, Progressive, Travelers, etc.)
Use a car insurance calculator to estimate what you should be paying
Compare apples to apples — same coverage limits, same deductibles
Rule #2: Don’t buy coverage you don’t need
If your ride is more than eight years old and worth less than $5,000, full coverage might not be worth it. You could be paying $70–100 a month for protection that wouldn’t even cover your car’s value in a total loss. Instead, consider:
Dropping collision and comprehensive if your car’s value is low
Raising your deductible — going from $500 to $1,000 could cut premiums up to 10%
Rule #3: Use pay-per-mile to your advantage
If you drive less than 8,000 miles a year, check out pay-per-mile insurance. Some drivers in California and Illinois are paying under $40/month by switching.
Rule #4: Stack every discount you can
Insurance discounts are like coupons — they’re useless if you don’t ask for them. Stacking two or three can easily drop your premium by 20% or more. Ask about:
Bundling auto + home or renters (saves 5–20%)
Safe driver or defensive driving courses
Good student or low mileage credits
Paying in full or auto-pay options
Rule #5: Don’t fall for “cheap” without checking the fine print
That rock-bottom quote might hide bare-minimum coverage that won’t help you when it counts. Always check:
Bodily injury limits (at least $50,000/$100,000 recommended)
Uninsured motorist coverage (essential if you live in high-claim states)
Rental reimbursement and roadside assistance options — the most popular policy add-ons for a good reason
Rule #6: Watch your credit like a hawk
Yes, your credit score still matters. In most states, drivers with excellent credit pay 40% less than those with poor scores. A 20-point bump could mean $200 back in your pocket annually.
Bottom line
It’s late October 2025, and renewal season is in full swing. Don’t wait until rates climb again in January. Compare quotes today using an unbiased car insurance calculator — not the one your insurer wants you to use. The driver who shops, wins. The one who doesn’t, pays for everyone else.
🌴 Find the cheapest travel insurance for your holiday trip
So you packed your suitcase and bought your place ticket — the next smart move is securing travel insurance. But the truth is, plenty of travelers overpay for underwhelming plans. You don’t need to overspend. With a few tips, you can lock in solid protection without blowing your travel budget.
What “cheap” really means — and where to draw the line:
The lowest‐price travel policies start around $43 for basic coverage (for a $2,500 trip), with limited benefits like modest medical limits and restricted cancellation options. Tin Leg’s basic plans often lead the pack for ultra-budget travel insurance.
For a little more (often just $18–30 extra), you can bump up to comprehensive plans. These typically include better medical limits, stronger emergency evacuation, and more generous trip cancellation benefits. For most international trips, comprehensive plans strike a better balance.
So here’s the trick: don’t just chase the lowest price — compare cost vs. coverage. Sometimes the “cheaper” plan leaves you exposed to big risks.
7 tips to get better insurance for less:
Buy early (preferably 7–21 days after booking) — It gives you access to waivers for pre-existing conditions and better CFAR (Cancel-For-Any-Reason) options.
Compare across insurers and tiers, not just policies — Same trip, same dates, different companies. You’ll often see big price spreads.
Skip CFAR unless you truly need flexibility — It boosts premiums by 40–60%, and usually reimburses only 50–80% of your costs.
Match medical coverage to your risk — If you’re healthy and your domestic plan has good overseas coverage, you might do fine with $50K limits. If you're older or traveling in places with expensive medical care, push for $100K+.
Use annual/multi-trip policies if you travel often — They can pay off if you take 2+ trips per year.
Check and add optional coverages only when needed — For example, adventure sports or trip cancellation beyond standard events.
Watch age and destination impacts — Older travelers often pay much more. Countries with high medical costs or remote locales drive up premiums.
Don’t settle for whatever your airline offers at checkout. Compare plans side by side, buy early, and get the coverage that fits your trip (and risk tolerance). That way you travel confidently without paying for insurance gaps or overpriced policies.
✈️ Unlock the BOGO travel hack: 120K points + the Companion Pass with Southwest
If you love flying two-for-one, this is your moment. The Southwest Rapid Rewards® Performance Business Credit Card from Chase is offering a massive 120,000-point bonus after you spend $10,000 in the first three months. That’s your fast track to the Companion Pass, the rare perk that lets your favorite travel buddy fly with you for just taxes and fees.
Why this deal is so sweet
120,000 bonus points is a killer offer!
The spend requirement ($10K in three months) looks aggressive but is manageable if you’ve got large purchases planned.
Once you qualify (by hitting the points threshold in a calendar year), you get the Companion Pass for the remainder of that year and all of the next year.
If you time it right, you could hold the Pass for nearly all of 2026 and all of 2027. Two full years of buy-one-get-one travel with a designated companion — that’s a powerful perk.
How to make this work for you:
Apply in October or November 2025 so you’re ready to go come 2026.
Plan so most of your $10K spend in January to February 2026. The reason: the bonus points count toward the calendar year you post them. If they hit within that time frame, they count for 2026 and you lock in the Companion Pass through 2027.
Track the qualifying points. Your total will include:
120,000 bonus points
The points you earned by that $10K spending
A built-in 10,000-point Companion Pass qualifying boost you get simply by having the card each year.
Together these get you over the ~135,000 qualifying points needed in a calendar year.
Use it wisely. Once you’ve unlocked the Pass, you can pick one companion who flies with you for free. You’ll just pay for the taxes and fees on any Southwest flight. That’s a serious value if you fly more than once or twice a year.
Stay eligible. Keep the account in good standing, and know that the Pass is valid through the year you earn it plus the next full year, so timing your qualification is key.
Getting the card is right for you if:
If you frequently travel with a companion on Southwest flights, or plan to.
If you have the ability (or business) to allocate $10K spend in a short window, or can plan accordingly.
If you want the luxury of a free companion seat every time you fly with Southwest (for just taxes and fees to pay).
HOWEVER, if you rarely fly Southwest or won’t meet the spend, then this might not be worth it for you. But for many frequent flyers this is a high-value move.
If you’re eligible, this is one of the strongest routes to unlocking the Southwest Companion Pass with a single card. Applying now and aligning your spend can mean two years of almost-free travel for you and a designated companion.
Spend your money on the things money can buy. Spend your time on the things money can’t.
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The MoneyGeek Team
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