1. Dial 800 for a lower cable bill
Call your cable/internet provider and tell them you're going to switch to Dish or DirecTV or Time Warner, or whichever other competitor exists in your local market. The first representative usually will give you a standard line or offer some minor bonus (like a premium channel), but hold out for the real deal when you get transferred to "I'm serious about cancellation representative," which is the company's last line of defense. I pull this stunt annually with Cablevision (hello!) and get their $85 "Triple Play" new subscriber promotion or an equivalent discount each time (rather than about $130). The vast majority of subscribers won't bother making this call. Don't be a statistic. I should have been out three times already but Cablevision makes more money when I'm on the roster.
Estimated annual savings: Anywhere from $100 to $450 depending how persuasive you are.
2. Slash your car insurance bill
Your ability to do accomplish hinges on (1) availability and (2) your ability to not drive like an a**hole. To the first point, begin by calling your insurer to find out if it offers a discount if you take a defensive driving course. Many states offer discounts of 10% or more, or remove points from your license for completing the course, which in effect will help lower the insurance rate. You may even be able to take the course online where you can take breaks to road rage during a Mario Kart session.
Estimated annual savings: Potentially $240/annually (based on $200/month insurance lowered 10%).
3. Know the right time to buy... stuff
For example, now's the best time to buy golf clubs while April is the right time to snag a good price on sneakers and cruise tickets. Merchants are willing to pull less from your pocket for certain products (or services) at different times throughout the year when they need to get rid of inventory, during holiday seasons and so on. Check out Lifehacker's complete chart so you can get all your ... stuff ... at the right time.
4. Less than extreme couponing
You don't have to go batsh*t level and become a TLC-certified extreme couponer to save a lot of cash here. Stores will effectively give you money if you're willing to spend a bit of time preparing before to a grocery trip; the epic battle between laziness and time and money. Best thing to do here is identify the products you buy consistently, whether it's paper towels or Oberto beef jerky. Go to coupons.com or a similar site or just Google "product" and "coupon" and you can print 'em out or have them mailed to you if you want to go next level. Best part here is, most grocery stores will "double" the coupon, i.e. trim twice the face value of it from your bill.
Estimated annual savings: If you use only five 50-cent coupons (doubled) every time you shop and shop once a week, that's $250, also known as NFL Sunday Ticket.
5. Make a Deal
Same principle: save money by spending a few minutes to see if there's a discount at a deal site for something(s) that you buy regularly, or were going to purchase anyway. You can find steep discounts on everything from electronics to diapers (adult or children's) at sites like Slickdeals, Woot and FatWallet; there's also coupon codes for retailers at retailmenot.com and you ought to be familiar with the Groupon model by now. Key here is, avoid buying stuff you don't need just because it's a "good deal." Spending only $100 for a $250 fax machine you won't use isn't a deal -- it's an expensive footrest.
Estimated annual savings: Varies
6. Brown bag it to work
Not a 40 oz. -- your lunch. You don't even have to make a cold cut sandwich necessarily. Buy a bunch of frozen meals that go for about $3.99 apiece (or less) and pack it with some fruit or chips and a bottle of water from a 24-pack -- rather than the $1.50+ from a typical vending machine. Chances are your Seamless or takeout order goes for double what your own lunch would cost, on average. And I love Subway as much as the next guy but there's only so many times I can shove an Italian B.M.T. into my face.
Estimated annual savings: Bring your lunch only twice a week at an average savings of about $5 per meal for $500 annually, and that's if you're spending only $10 on wherever you usually get lunch. Do it full-time and you're looking at about $1,300-plus.
7. Go big then go home
Buy things you use regularly in bulk. Order on Amazon or at BJ's or Costco or wherever things are sold for giants. Now you can't go on a shopping spree there because it's tempting: everything is cooler in mammoth quantities, even sponges. But if you stock up on the right items and avoid buying heavily marked up goods, it can go a long way.
Estimated annual savings: Focusing solely on the bathroom trio of razors, toilet paper and deodorant, the answer is ... a lot. It's hard to quantify because, for example, some of us are TP folders, other bunchers, but those three items come to drastically cheaper when you buy a heap at once.
8. Trim the fat
Are you a "Homeland" fanatic? Great. How often do you watch other Showtime programs? Getting crushed at work, or travelling, leaving your Netflix queue lonely and scared? Put Netflix on hold for a few months until you can devote time to an "Archer" marathon. Cancel Showtime when it's out of season for your show(s). Magazine subscription you simply don't need? You get the idea.
Estimated annual savings: Cancel one premium channel for eight months when you're not using it and freeze Netflix for four months, and you've got about $130 for the year for only two phone calls.
9. Cut your own hair
Potentially dangerous one here and I wouldn't advise watching "how to cut hair" on YouTube, but if you simply buzz or bic your head, it's hard to screw up with a set of clippers that will run you about $30 dollars. You may simply like the barber experience as I do, which is why I rotate between buzzing myself and sitting back at Dominick & Vincent's with a newspaper while the delicious scent of talcum powder passes through the nostrils.
Estimated annual savings: Cut the hair yourself 12 times and save about $170, minus your investment in clippers. And when you do it yourself the shop's always open and there's never a line; time equals money.
10. Redeem those devious gift cards
So you received one of those prepaid credit cards, which are decidedly better than unwanted clothing. Only the card might expire in your state and you might get rejected somewhere if the balance doesn't cover the entire purchase. Point is -- they can be tricky. Solution? Use the card to buy an Amazon gift card, then spend away without restriction. Bonus: Go to Plastic Jungle to sell a store-specific gift card you simply don't want.
Estimated annual savings: Enough.