Let’s Get Real about Earning Points and Miles Toward Free Travel

I recently read an article in Rolling Stone about a 25-year-old blogger who has been obsessed with planes and the airline culture since he was a boy. Through constant research and networking with others who share his passion, he has mastered a system of acquiring travel points and rewards that has kept him in the skies, flying around the world in first-class accommodations for months at a time. According to the article, his skills and strategies for cracking codes and systems rival those of a professional gambler who pushes the limits of propriety to “beat the house.“

There have been many articles and a lot of blogging about traveling for free with points and rewards gained through loyalty programs and credit card spending. Many of these authors are young adults who have turned this travel currency into some seriously lucrative careers. Their articles are exciting to read and full of dreams of possibilities. But, the young minds that pursue the goal of free and never-ending travel are generally void of the everyday responsibilities that accompany life in the world where most of us live. So, let’s get our heads out of the clouds and back to a familiar horizon called reality.

new york city skyline

I’m an advertising professional who has navigated the credit card industry for 35 years. I began this incredible career as a youngster, much like those referenced above, in New York City – the center of the business world back then. The popular marketing tool in those days was the direct mail package that brought generations the good news that they were approved for instant credit via credit cards.

When I first entered the world of financial advertising, loyalty programs were just being launched. And, I was sitting in a professional position that offered me intimate knowledge of the terms and policies of major players like American Express®, Citi®, JPMorgan Chase, Barclays, and U.S. Bank. It wasn’t too long before co-branding became popular, and in no time, I was working on campaigns for other renowned businesses across a multitude of industries that would include giants like Ritz-Carlton®, Marriott®, Hyatt®, Wyndham®, US Airways®, Southwest®, United®, Walmart®, Subaru®, Starbucks®, AARP, Amazon®, Amtrak®…yea, yea, I know. That’s enough namedropping for now. It seemed as though everyone wanted to be partnered with everyone else, and before long I had more than 450 co-brandings and product launches under my belt.

Within a few years, I decided to break away from the herd, and a friend and I started our own direct mail business. Over the years, we managed to clog just about everyone’s mailboxes with loyalty program offers, and my friends began to call me “the junk mail queen.” This title stemmed primarily from the evolution of postal mailbox offers to email inbox offers. We’ve come a long way, baby.

So, what’s the purpose in revealing my extensive credentials? It’s to assure the reader that I know my stuff when it comes to these offers and their fine-print restrictions. And, this advantage has made it possible for me to choose credit cards that turn my everyday spending into countless treats.

I’ve had many requests from family and friends to help decipher the maze of charts and points per “spend” in order to determine the value of their earned rewards. So I decided that sharing some relatively simple advice and some actual experiences might just be beneficial to a community of consumers who could use a little hand-holding when determining how their spending habits can be used to their advantage – and lessen the sting of making their credit card payments every month.

To pull this off, I’ve enlisted an amazing crew of seasoned pros like me who have been in the “points” business for decades. Some are from the creative side of things and are the “talent” behind many credit card campaigns you’ve seen on TV or in the mail. Others are from the account management side, and have worked one-on-one with top executives at all the major credit card companies and banks. We also have a great group of writers here who quite simply know how to make each blog post interesting and informative. So that’s the talent team behind PointSavvy.

Since the 90s, I’ve been a complete junkie for points or miles that can get me and my family to a place of peace and tranquility – preferably first-class ocean view accommodations at world-class luxury hotels. And you know what? Sometimes that’s not too much to ask, if you play your cards right.

Barbara Jones

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Editorial Note: Opinions expressed here are author's alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.