4 smart rewards card lessons from America's teachers

Points help these educators score free travel, cash back cuts cost of school supplies

Susan Johnston Taylor
Personal Finance Writer
Writes about credit card technology and savvy card use

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Budget-conscious teachers know how to stretch their dollar, whether it’s buying supplies for the classroom or planning their summer getaway, and often that includes smart use of credit card rewards.

With school just starting across the country for students, class is now in session for card-savvy adults, as these teachers and one retired school administrator share their best credit card strategies to score free travel and cash back.

Jackie Sills-Dellegrazie in Patagonia.

    Jackie Sills-Dellegrazie in Patagonia.

Lesson 1: Get organized.
Jackie Sills-Dellegrazie, an elementary reading specialist in New York City and founder of The Globetrotting Teacher blog, got into travel hacking by accident when she and her husband were planning their honeymoon in 2006.

“We had all these points and didn’t know what to do with them,” she says. They ended up using their American Express Member Rewards points to fly to Italy. After that, they decided to get more strategic in how they earn and redeem credit card rewards.

Since then, she’s traveled to four continents and close to 30 countries using airline miles and credit card points. In 2016, she went on a solo hiking trip in Patagonia, spent 10 days in Eastern Europe with her husband and took her mom to visit Europe’s Christmas markets.

“A lot of your everyday spending, your cellphone, your vet bills, doctor copays and car insurance, can be paid with a credit card,” she says. “All those little things add up and add incredible value. I’m really big on trying to maximize every dollar I spend.”

Sills-Dellegrazie has about 10 credit cards, which she keeps organized in a spreadsheet.

“I color code it,” she explains. “With a new card, it’s in red if I haven’t met the minimum spend requirement” to earn the sign-up bonus.

Also, because the school calendar dictates when she can take vacations, she plans her travel carefully. For instance, she booked her and her husband’s awards flight to Prague 10 months in advance.

“You have to be a really solid planner as a teacher,” she says. “You can’t just grab a random awards seat. You need the dates that you need.”

Vicki Cook on the beach.

    Vicki Cook on the beach.

Lesson 2: Go for the Companion Pass.
Vicki Cook is a recently retired school administrator in Rochester, New York, who runs the personal finance blog Make Smarter Decisions. Now that both she and her husband are retired, they’re looking forward to more time to travel and they earned the Southwest Companion Pass to do that.

“We fly on one person’s rewards,” she says. “You don’t have to pay [for a second ticket] other than the taxes. Now we’re going to have more flexibility, so we should be able to use points on off days and stretch them further.”

Using the Companion Pass, they booked flights to Dallas for a conference in 2016 and used it to visit their condo in Sarasota, Florida, earlier in 2017.

To earn the pass, which is good for the remainder of the year in which it’s earned plus the following year, you need to accumulate 110,000 qualifying points or take 100 one-way qualifying flights in a calendar year. Cook earned 110,000 points through the sign-up bonuses for a Southwest personal credit card and a business credit card.

They use the business card for expenses on their rental properties.

“We can charge utilities, a lot of supplies, and we can charge our insurance,” she says. “We got 2,500 miles for our insurance, which is about half a flight.” (Some other credit cards offer companion passes, but those tend to be more restrictive than the Southwest Companion Pass.)

Cook also uses a shopping portal to accrue more rewards.

“We had to order a refrigerator a few weeks ago for one of the rentals,” she says. She clicked through her credit card’s shopping portal before ordering from Home Depot. “We earned 1,496 points when others might use their card and only get 498 points,” she adds. 

The Klines parasailing.

    The Klines parasailing.

Lesson 3: Revisit your card strategy.
Brittany Kline is a fourth-grade teacher in Rochester, New York, who with her husband Kelan Kline, runs The Savvy Couple, a money-saving blog. Since getting married in 2013, the Klines have used credit card rewards to purchase items for their home.

Sometimes Brittany also uses cash back card rewards to order supplies for her classroom. They’re now saving up credit card rewards to take a family vacation next year, possibly a Caribbean cruise.

Two ways they accumulate points quickly: Sign-up bonuses from opening new credit cards and putting putting group meals on their cards.

“Anytime we go out with friends or family, we’ll treat that night and pay for it with our credit card. Then everyone will pay us back at a later time with cash that night or do PayPal or Venmo,” says Kelan.  

Because reward offerings – and the couple’s needs – change over time, they revisit their credit card strategy regularly. They also track new promotions that fit with their current strategy.

“Every couple of years we’ll analyze what our goal is with our cards,” Kelan says. “Lately it’s been travel. We keep an eye out for new cards and switch every few years and earn that upfront rewards bonus.”

Lesson 4: Score sign-up bonuses with everyday spending.
Tracking multiple credit cards and always shopping through a credit card shopping portal to garner the most rewards isn’t for everyone. Debra Spector, a sixth-grade teacher in Galt, California, prefers a strategy of maximizing rewards with sign-up bonuses – and then switching cards.

Debra Spector on vacation.

    Debra Spector on vacation.

“We don’t want to become bogged down with program rules and requirements,” she says. She and her husband open a new card, earn the sign-up bonus through their everyday spending, redeem the points and then close the card before the annual fee kicks in, a strategy known as credit card churning.

Spector recently redeemed enough miles on her American Airlines card for a flight to Chicago to see family and go sightseeing for a day.

Right now, they have three credit cards (one of which is their “hideaway card” for emergencies, not a rewards card).

While they’re trying to earn a new card’s sign-up bonus, “we put almost everything on that credit card, including groceries, and we pay it off monthly,” she says. “All our bills that are automatic payment, we have them set up on a rewards card.”

Her daughter is in college, so some of her college fees also can be paid via credit card, and those points add up quickly.

Spector also stays loyal to two airline mileage programs, Virgin and American Airlines. “Otherwise our miles are too thin and spread out among too many reward programs,” she adds.

One final tip: Remember to always, always pay your credit card balance in full and on time, since rewards cards tend to carry a higher interest rate than more basic credit cards. 

What’s your credit card strategy success story? What lessons have you learned in handling your credit cards than may be able to help others rack up miles for a dream vacation, savor a meal cooked by a celebrity chef, or bank enough cash back to put a dent in your family’s back-to-school or holiday shopping? 

Email or tweet to me, so I can share your tips and tricks in a future story or blog post. I’m Susan Johnston Taylor. Drop me a line at susan@susan-johnston.com or tweet to me at @UrbanMuseWriter

See related: Video: Saving on back-to-school shopping, Ways to rack up points for last-minute, back-to-school shopping, 3 ways to maximize rewards on back-to-school shopping5 apps to turbocharge back-to-school savings


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Updated: 11-23-2017