How I Did It: Finding a Second Career in Couponing

A perfectly timed speaking gig about coupon clipping at her local Huntley, Ill., library led Jill Cataldo to her second career as a coupon expert. "The librarian told me I'd be lucky if 23 people showed up," she says. "I had 162 people come."

That was in August of 2008. A month later, Cataldo lost her job as a web developer, and around the same time, another library invited her to speak. "I thought 'I'm not doing anything else. Maybe this is what I should be doing,'" says Cataldo, 37.

By October, Cataldo had an offer to write a syndicated column on couponing, and she hasn't looked back since. Today she's created a mini couponing empire: syndicating her column to more than 20 million readers, filming two DVDs and consulting on the subject across the country. The next step, she says, might be television, but she's still reviewing proposals. "I was never afraid to reinvent myself," Cataldo says. "I've taught aerobics, and I even worked on a garbage truck for two summers. I'm not afraid to try something new."

Cataldo still gets a thrill out of cutting coupons, which she says shouldn't take more than 30 minutes a week. "To see what you would have paid and what you're going to pay (with coupons), it's like going to the casino knowing you're going to win every time," she says.

Here are her eight best tips to be sure you win every time you're at the store:

1. Don't use coupons the same week you clip them. Cataldo says this is one of the biggest mistakes she sees. Stores know in advance what coupons will be offered, so prices on those items will be higher.

2. Save coupons for when the items are at their lowest price. Most coupons have an expiration date 30 to 90 days out, which allows you to take advantage of lower prices. The same box of cereal can cost from $1.49 to $3.99, Cataldo waits until the cereal costs $1.49, and then using her dollar-off coupon, she gets it for 49 cents. "A lot of using coupons is about playing those cycles," she says. "Once you understand that prices are constantly in rotation, that's the biggest light bulb moment," she says.

3. Use coupon-matching websites. There are great sites out there that track store sales and give you printable coupons, including SavingsAngel, CouponMom and The Grocery Game.

4. Stack coupons. Combine manufacturer coupons with store-specific coupons -- that's when you really start saving money, Cataldo says.

5. Shop for lower prices rather than specific brands. You can't be brand-loyal, Cataldo says. "During a price cycle, one brand might be cheaper than another, so it's important to constantly shuffle around." But if you do prefer, say, a certain brand of toothpaste, wait for it to go on sale, then buy a few extra tubes, she advises.

6. Local grocery stores offer better deals than big box stores. "An everyday-low-price store actually stays right in the middle on most prices," Cataldo says. "They might have lower prices than those of grocery stores during the high points of the cycle, but they're higher prices than the low point of grocery stores' cycles."

7. Store brands aren't usually cheaper. The price of a store brand doesn't really change, Cataldo says. "National brands will fall into lower price ranges, and that's when you use the coupons," she says.

8. Coupons aren't only for groceries. Housewares, clothing and toys all go on sale in very predictable ways. For instance, January is the best time to shop for toys, the end of summer is the best time to shop for school and office supplies, and September is an optimal time to buy patio furniture. "Don't forget to use those department store $10 off any purchase deals," Cataldo says. "Even if I don't have anything I need, I'll use those for things like socks and underwear. I'll take $10 off $10 anytime -- that's beautiful."

Read more at Second Act:

Cut Your Grocery Bill in Half (And Other Stories)

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