This Week’s Money Map:

• 🚗 Safe driver discounts — When they save you money (and when they don’t)

• 💵 Holiday hustles that actually pay

• 🚨 Why health insurance costs could skyrocket and what you should do NOW

• 🌴 2025 holiday travel playbook: When to book and where to go

🚗 Safe driver discounts — When they save you money (and when they don’t)

Many insurance companies now offer telematics programs (think plug-in devices or mobile apps) that track driving behavior like speed, braking, cornering, and mileage. And they often offer significant discounts when you opt in. But here’s what most people don’t realize: that same discount might actually raise your rates depending on how it’s set up and how your insurer uses your driving data.

The “safe driver” promise vs. the real trouble
At its best, this program is genius. Drive carefully — no hard stops, no speeding, limited night driving — and the algorithm rewards you with lower premiums. It’s data-driven fairness in theory: you pay based on how you actually drive, not how others in your ZIP code drive.

But here’s the catch: not all “safe driver” programs play fair.

Once the insurer starts collecting your data, that information doesn’t just disappear after your discount kicks in. It’s used to constantly “adjust” your risk profile. If your driving patterns change — say, longer commutes, late-night shifts, or one too many hard brakes (even if it’s avoiding a squirrel) — your next renewal could bring a surprise increase.

According to a study from the Maryland Insurance Administration¹, at least 24% of drivers enrolled in these programs actually saw their rates go up after renewal, not down. And 45% saw no change in their next year’s premium cost. The problem isn’t the tracking itself — it’s that you usually don’t know how you’re being scored. 

When data tracking makes sense
Here’s when opting into your insurer’s telematics program could be beneficial:

✅ Short, consistent commutes
If you drive mainly during daylight and stick to well-maintained local roads, telematics often helps you save. The fewer variables you face — like unpredictable weather or high-speed highways — the “safer” your data looks. 

✅ Hybrid or remote workers
Telematics rewards low-mileage drivers who only run short errands or commute a few days a week. 

✅ Drivers in safer regions
If you live in a suburban or rural area with low congestion and minimal stop-and-go traffic, your data likely paints a rosy picture. Fewer abrupt stops, steadier speeds, and less nighttime driving all help you look like the poster child for “safe driving.”

When it doesn’t make sense

🚫 Long-distance commuters 
More time on the road = more exposure. Even perfect drivers rack up more “risk hours,” which the algorithm can interpret as higher accident probability.

🚫 Night-shift or weekend workers 
Driving between midnight and 5 a.m. often triggers penalty points because insurers classify those hours as “high risk,” even if your routes are quiet and safe.

🚫 City drivers or delivery workers 
Heavy traffic, sudden stops, and constant lane changes can make even careful drivers look “aggressive” to a sensor that doesn’t understand context.

How to make data tracking work for you

1. Ask before you enroll — Request clear details on what’s tracked, how it’s scored, and whether your rates can increase.

2. Try a short-term pilot — Many insurers offer trial periods where you can test the app without it affecting your rate.

3. Use your state’s consumer protection site — Verify how your data can be used or shared.

4. Compare multiple insurers — Looking for insurers that play fair? These car insurance providers are known for transparent policies and balanced pricing.

5. Check your rate every renewal — Think your discount’s still competitive? You might be surprised. Compare real car insurance quotes online and see how your rate measures up without agent bias.

When used wisely, safe driver programs can reward good habits and put real money back in your pocket. Used carelessly, they can turn your daily commute into a pricing experiment.

💵 Holiday hustles that actually pay

October’s here and your wallet could use a little extra love before holiday chaos hits. The fix? Launch a side hustle now with what you already know, own, or love doing.

Turn your talents into cash
Got a creative streak? People pay for festive flair this time of year. Holiday photographers, dance teachers, event planners, singers, and decorators are in high demand from October through New Year’s Eve. If you’ve got a camera, a voice, or an eye for sparkle, that’s a business waiting to happen.

Proven small business ideas with real demand
Some side hustles grow faster than you expect. These are tried-and-tested small business ideas that do well every holiday season:

• Event planning, hosting and coordination (office parties, weddings, holiday dinners)

• Gift basket services (personal or corporate)

• Catering or baked goods (cookies, charcuterie boxes, holiday treats)

• Print-on-demand merch (funny holiday shirts, mugs, tote bags)

• Delivery driving (apps like DoorDash, Instacart, and Uber Eats boom in November and December)

• Errand running (help people wrap and deliver gifts, mail packages, or shop for groceries)

Protect your profits
Here’s the thing most hustlers forget: one accident, one bad client, one stolen laptop — and your hard-earned side income could vanish. That’s why business insurance isn’t just for big companies. It’s for you — the photographer, videographer, make-up artist, events coordinator, decorator, baker, or gig worker who’s making things happen this holiday season.

Whether it’s general liability (someone trips), property coverage (your gear breaks), or professional liability (a client claims your work cost them money) — small business insurance is your safety net. And it’s surprisingly affordable.

The holidays are your chance to shine and stack extra income before the year ends, but the key is to start now. Get your idea rolling, promote it locally or online, and make sure you’re covered. Because nothing says “peace on earth” quite like knowing your side hustle and your wallet are protected.

🚨 Why health insurance costs could skyrocket and what you should do NOW

The extra subsidies (tax credits) for Affordable Care Act (ACA) plans are set to expire at the end of 2025, unless Congress acts quickly to extend them. These subsidies have been keeping premiums reasonable for low- and middle-income folks. Remove them, and many people will be pushed to choose between paying more than they can afford, skimping on coverage, or dropping it altogether. Here are the numbers:

• Average premiums for subsidized plans could more than double, soaring from about $888 (2025) to $1,904 (2026)

• Millions of people could lose their subsidy support or become uninsured entirely

• On average, premium payments (after subsidies) could jump over 75%

Translation: the health insurance system is on the brink. If you rely on marketplace (ACA) plans — or might in the future — you need to pay attention.

How this impacts you 
You might be thinking: “None of this applies to me, I’m insured through my job,” or “I’m healthy, I don’t need insurance now.” Fair, but here’s what you should weigh:

• Unexpected life shifts — Job changes, gig work, losing employer coverage, crossing income thresholds — life doesn’t wait for “safe zones.”

• Medical bills don’t care about your budget — Without insurance, even a broken bone or ER visit can send you into financial crisis.

• You may unknowingly lose help — Many don’t realize they do qualify for assistance — 14.5 million people uninsured in 2023 were actually eligible for either Medicaid or subsidies. 

What you should do before open enrollment

1. Mark your calendar: Nov 1, 2025 — Jan 15, 2026
That’s your main window to enroll in or change ACA Marketplace plans (in many states). Some states have slightly different deadlines. 

2. Estimate your 2026 income 
Why? Because subsidies and eligibility depend on what you expect to earn. If you expect a raise, a new side gig, or a drop in income, factor that in. Get a rough ballpark now.

3. Use a reliable health insurance calculator
MoneyGeek’s free online health insurance calculator helps you decide whether to lock in a plan early or adjust contributions to lower your taxable income.

4. Look at alternative coverage options
If you don’t qualify for subsidies or ACA plans become too expensive, you can check if you qualify for Medicaid or state-level safety nets. Employer plans can also help, even through your spouse or partner. Just make sure to read every word of your policy. These are not “full coverage” in many cases. If you’re healthy but don’t want surprise health bills, consider locking in a plan with more coverage, even if premiums are higher now.

Don’t wait for Congress to decide your fate. Start reviewing your 2026 health coverage options this month, while plans and prices are still flexible. Check your eligibility, update your income estimate, and compare quotes early, even if you don’t plan to switch yet. Because when subsidies expire, waiting could cost you thousands.

🌴 2025 holiday travel playbook: When to book and where to go

It’s mid-October and the Halloween décor is in full swing. But the real scare isn’t the fake skeleton on your neighbor’s porch. It’s the price of holiday flights if you wait another week. Airfare’s already creeping up, airports are bracing for chaos, and the smartest travelers? They’re booking right now, quietly snagging deals before the rush hits.

Best times to book (and fly)
Here’s the insider breakdown:

• Thanksgiving: Book by October 16th for the best fares. Flying Tuesday before or Friday after Thanksgiving usually costs less than the infamous Wednesday rush.

• Christmas and New Year’s: The sweet spot is 6 to 8 weeks out (yep, that’s now). For savings, fly on the holiday itself — December 24th or 25th — and return on New Year’s Eve or January 2nd–3rd.

Where to go
Orlando, New York City, and Las Vegas are topping the charts for domestic travelers, while Cancún, London, and Tokyo lead the international wish lists. Ski lovers are flocking to Denver, Salt Lake City, and Banff, while families are eyeing warmer escapes like Hawaii and the Caribbean.

Want to stretch your dollars? Skip the usual hotspots and go for under-the-radar gems like Savannah, GA, Portland, ME, or Santa Fe, NM — all offering charm without the crowds (or premium prices).

• Bundle and save: Packages that combine flight and hotel often run 10–20% cheaper.

• Use fare trackers and hidden-city tricks: Tools like Hopper or Skyscanner can alert you to secret discounts.

• Pro tip: Use Google Flights’ “Price Graph” to see fare dips, and set alerts now.

October promos you shouldn’t miss
Many travel credit cards and airlines are sweetening the deal this month:

• Chase Sapphire Preferred® and Capital One Venture Rewards are both running limited-time 75,000-point bonuses for new cardholders 

• Airlines like Delta, United, and Southwest are offering early holiday sales through mid-October — up to 35% off select routes.

• Some even include bonus miles if you book through their app this month.

Why travel insurance is your life saver
Here’s the part most travelers skip and regret later. Flight delays, lost luggage, or sudden illness can wipe out thousands from your wallet. And with airlines still juggling staffing shortages and unpredictable weather, trip disruptions are spiking. Travel insurance isn’t just “nice to have” anymore — it’s your financial seatbelt. A solid plan can cover:

• Cancellations (weather, illness, or emergencies)

• Lost baggage and delays

• Medical care abroad

• Trip interruptions (if plans change mid-journey)

October is your golden window. Prices will rise. Seats will vanish. And those “I’ll book next week” moments will cost you. Lock in your flights now, check your card rewards, and for the love of travel, get insured before you fly!

Smart Cents gives you actionable tips and mindset shifts to help you reach your financial happy place. Thanks for being a part of our community.

The MoneyGeek Team

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1  Maryland Insurance Administration. Telematics Survey Report Auto Insurance Market in Maryland. July 2025: (https://insurance.maryland.gov/Consumer/Appeals%20and%20Grievances%20Reports/Telematics-Survey-Report-2025.pdf)