Your October Financial To-Dos

“Bittersweet October. The mellow, messy, leaf-kicking, perfect pause between the opposing miseries of summer and winter.”

Don’t judge us for quoting Carol Bishop Hipps–there’s something about October. Maybe it’s the fact that we’re finally, indisputably ensconced in autumn. Maybe it’s the fact that we can break out the cable-knit, go apple-picking and pumpkin-gathering, and brew hot chocolate with a clear conscience.

Once you have that hot chocolate firmly in hand, turn your attention to your October financial to-dos: From health insurance to trick-or-treaters, we’ve got you covered.

Take Advantage of Open Enrollment. Deadline: Wed, Oct. 3

Open enrollment is the period when you’re allowed to select your health care plans for the next year. If your health insurance is through your employer, check with HR immediately (seriously: now!) to make sure you know when your employer offers open enrollment. As an example, Medicare is holding open enrollment October 15-December 7th for 2013 benefits. Don’t be shy about asking HR or other experts for guidance–refusing to ask is one of the most common and critical mistakes a person can make during open enrollment. We also have information on how to approach open enrollment and what not to miss.

Plan Halloween. Deadline: Wed, Oct. 10

The last-minute hustle for costumes/candy/decorations in the last week of October is a dream come true for retailers, but a nightmare for us (“I’m a … sleepy person in pajamas?”). Take your Halloween plans into account now and start laying the groundwork: Look for sales on candy for trick-or-treaters, figure out exactly what you’ll need for a costume if you’re wearing one and start hunting down the pieces. And, of course, survey your options to buy the most affordable pumpkin-turned-jack-o-lantern. By getting things under control now, you’ll avoid the rush–and the spending!–later.

Assert Yourself. Deadline: Wed, Oct. 17

We all know that we’re allowed to negotiate for a raise, or with jewelry vendors on the street. But there are many more opportunities to get the best price. Since we’re spending a little more time inside, why not put it to good use? These five surprising things to negotiate (gym memberships!) are a good place to start. For more information on what to negotiate and exactly how to do it, sign up for our free Cut Your Costs Bootcamp, which will help you shrink your bills and find a little money to spare.

Reassess Your Budget. Deadline: Mon, Oct. 22

Go to the LV Money Center to make sure you’re sticking to your current budget. You may have readjusted over the summer for vacation spending (this is how not to blow your vacation budget), so make sure you reallocate your funds for fall spending, whether that means textbooks, back-to-school wardrobes (more on back-to-school budgeting) or increased IRA contributions. Adjust your numbers if your income, goals or lifestyle has changed.

Batten Down the Hatches. Deadline: Wed, Oct. 31

By October, you can’t deny that winter is coming. Before things get too cold (or wet, depending on where you’re living), get your winter chores out of the way. Depending on your situation, you might want to:

• Bring in patio furniture
• Buy or find snow tires
• Try on family winter coats and boots and find rogue gloves, hats and scarves
• Adjust your utilities budget in The Money Center to accommodate heating costs
• Get firewood

And don’t forget to look into what you should be buying this month in the guide below:

What To Buy When

• Jan
• Feb
• March
• April
• May
• June
• July
• Aug
• Sept
• Oct
• Nov
• Dec

Winter Boots, Clothing and Coats: Get in on winter sales now for the best selection	Suits: Around the new year, stores discount their fall suits	Perfume: A popular holiday gift, perfume is often on sale after the season	Home Furnishings: Retailers are making room for new inventory
Calendars: Just after the new year, prices are drastically reduced	Carpets and Flooring: Many people spruce up their homes during the holidays, so prices plummet afterwards	Big Appliances: Stock not sold during the holiday rush is now heavily discounted	Linens and Bedding: Ever-popular "white sales" make January the best month for these items
Holiday Supplies: If you're willing and able to store cards and wrapping paper for a year, you can find them now for up to 80% off	Office Furniture: Retailers cater to home businesses starting around the new year	Video Games: New games are released for the holidays, but you can get them marked down afterwards

Winter Boots, Clothing and Coats: The selection is sparser, but the sales are steeper	Perfume: Score a deal after Valentine’s Day	Homes: Bad weather keeps buyers at bay, so competition is weak, and sellers are eager
Home Renovations: You’ll pay less and get more attention from contractors, because few people renovate so early in the year	Bicycles: Retailers mark down older models to make room for new inventory in February and March	Cameras: New models come out in January and February, so buy last year’s version at a discount
Home Entertainment Systems: The best TV and home theater sales come just before the Super Bowl	Video Games: New games are released for the holidays, so you can get them marked down after the rush	Chocolates and Candy: Buy after Valentine’s Day, of course

Sweaters and Cashmere: Prices can be reduced by as much as 25% to 40% from the end of March through April	China and Flatware: Get in on inventory left over from the holidays	Air Conditioners: Don’t wait for the weather to get hot; demand is low now, as are prices
Gas Grills: As with air conditioners, demand and prices are low	Gardening Tools: Rakes, hoes, shovels and other gardening implements are as much as 50% off	Frozen Food: It’s National Frozen Food Month, so supermarkets celebrate with sales

Sweaters and Cashmere: Stock up now on next winter's sweaters with steep sales	Sneakers: In spring, stores entice warm-weather runners with sales	Vacuum Cleaners: Retailers slash prices now to make room for new models in June
Snow Blowers: Come April, demand is low, so scoop up one for next year	Office Furniture: Retailers cater to home businesses starting after tax season	Cruises: This is the season for repositioning cruises, which have fewer ports of call but are cheaper and of great value
Electronics: After the Japanese fiscal year closes at the end of March, retailers make room for new models of Japanese electronics

Sweaters and Cashmere: Prices can be reduced by as much as 25% to 40%	Vacuum Cleaners: Retailers slash prices now to make room for new models in June	Cookware: Graduation and wedding promotions mean you should buy pots and pans now	Refrigerators: New fridges come out during the summer, so stores are clearing space; negotiate a deal
Big Appliances: Stock not sold during the holiday rush is now heavily discounted	Patio Furniture: Warm weather means newer models, so buy last season’s styles now	Grilling Supplies: Get charcoal and lighter fluid before summer kicks into high gear and prices go up	Small Kitchen Appliances: Get your mixers and blenders now, when there are sales for wedding and graduation season
Party Supplies: Whether or not you’re throwing a graduation party, stock up on disposable plates, cups, etc.	Electronics: After the Japanese fiscal year closes at the end of March, retailers make room for new models of Japanese electronics	Mattresses and Box Springs: Stores want to make room for new models, so negotiate a good deal now

Men’s Suits: Father’s Day sales mean low prices	Tools: Father’s Day strikes again	Cookware: It’s not only wedding bells that are ringing—registers are ringing with sales of pots and pans
Paint: When it’s hot out, no one feels like painting … which is why it’s cheap at this time of year	Butter: Butter production is at its best in June and July, so prices are accordingly low; freeze for up to six months to make it last	Champagne and Sparkling Wine: There are usually deals for bubbly during the holidays and before June weddings
Gym Memberships: The outdoors beckon, so gyms are offering deals

Suits: Get a spring suit—in the middle of summer	Furniture: Retailers are clearing space to make room for new inventory	Big Appliances: Take advantage of Independence Day sales
Paint: When it’s hot out, no one feels like painting … which is why it’s cheap at this time of year	Butter: Butter production is at its best in June and July, so prices are accordingly low; freeze for up to six months to make it last

Flip-flops: Ever-useful flip-flops are harder to find later in the year; buy them now when retailers still have them in stock and they’re on sale	School Supplies: Back-to-school sales!	Trees, Shrubs, Plants: Nab end-of-summer deals late in the month, and store your plants according to instructions until next spring. Alternatively, buy bulbs, which you can plant whenever
Lawn Mowers and Swing Sets: Stores discount these summer items now to make room for fall products	Computers: Capitalize on back-to-school sales	MP3 Players: Stores want to get rid of old models before October when new styles come out and the holiday rush begins

China and Flatware: Get in on the inventory left over from wedding season	Wine: The harvest is coming in, so you can find eclectic wines from smaller wineries early in the season	Computers: Upgrade yours during back-to-school sales
Jeans: The remainders from back-to-school season are now available inexpensively for kids and adults	MP3 Players: Stores want to get rid of old models before October, when new styles come out and the holiday rush begins	Cars: Next year’s models have arrived, so dealers want to sell the current year’s leftovers, giving you negotiating leverage
Holiday Airfare: It’s about eight weeks before Thanksgiving, so make travel plans before flights book up and prices skyrocket

Jeans: The back-to-school sales continue, with sparser selection but steeper discounts	Swimsuits: Cash in on swimwear sales now through November	Big Appliances: Buy last year’s models now; shop during Columbus Day weekend, because stores celebrate even small holidays with sales
Air Conditioners: Temperatures are cooling, and so are prices	Gas Grills: Pick these up now for next summer	School Supplies: Back-to-school sales!
Toys: Retailers lower prices as early as October in order to maximize holiday sales	Cars: Next year’s models have arrived, so dealers want to sell the current year’s leftovers, giving you negotiating leverage	Health Insurance: Open enrollment may be your one chance to sign up for insurance for next year

Wedding Dresses: Wedding fever is at its lowest pitch now	Swimsuits: Swimwear is as much as 90% off, but selection is low	Cookware: Kitchenware becomes cheaper as the holidays approach
Christmas Trees: For the best selection, get your tree right after Thanksgiving; it’ll stay good for at least a month, and trees later in the season have been cut weeks earlier anyway	Frozen Turkeys: Buy one immediately after Thanksgiving, when grocery stores still have a glut	Toys: Retailers are slashing prices to maximize holiday sales
Electronics: Black Friday and Cyber Monday offer great deals on everything from TVs to computers

Wedding Dresses: The beginning of December is the slow season, so get in before holiday engagements	Televisions: In the run up to the holidays, stores have big sales on TVs	Pools: Off-season, you’ll find the cheapest prices, though maybe not the best inventory
Small Kitchen Appliances: Get your mixer and blender during holiday sales	Champagne and Sparkling Wine: Although these are in high demand, prices are also more competitive than usual	Frozen Meat: Buy this immediately after Christmas, when grocery stores still have a glut