5 Ways You Know You’re Winning in Travel and Loyalty Programs 5 Ways You Know You’re Winning in Travel and Loyalty Programs

5 Ways You Know You’re Winning in Travel and Loyalty Programs

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Recently I hopped onto Twitter to see what some of my miles & points folks were up to, and I came across this tweet by my friend Adam — also known as Travel Fanboy. He was responding to a post titled “Why You May be Losing the Miles & Points Game, Without Even Knowing It


No one wants to make the wrong move. And, if you want help learning about points and miles and how to use them, we have just the place to do so: our Facebook group Award Travel 101!

So, let's turn this mentality around a bit and discuss how you know you’re doing it right.

1. Taking the First Step

Learning and understanding travel rewards is tough for many of us. It takes a slightly different mental outlook to change any preconceived notions. If you’re anything like me, you may be risk- and debt-averse.

My family history dates back to some of the poorer areas of Europe. My great-grandparents immigrated to the United States in the late 1890s. Due to experiencing “The Great Depression” firsthand, my grandparents passed on many of the beliefs that debt was bad to my parents’ generation. We grew up with those beliefs ingrained into our mental fabric and looking past that mentality can be tough!

It's important to know that we here at AwardWallet and Award Travel 101 still believe that you shouldn’t carry debt. If you can’t pay off your credit card in full, the interest you'll pay will outweigh any rewards earned. Instead, you should focus on lowering your interest rate while you pay off your debt. If you're in this spot, taking the first step may start with one of these posts:

  1. Best 0% APR Balance Transfer Offers in 2021
  2. How to Get a 0% Intro APR without Paying a Balance Transfer Fee
  3. Best $0 Annual Fee Credit Cards with 0% Intro APR

If you're able to pay your balance in full each month, we have plenty of resources that can help guide you down the right path. You can start with:

  1. Back to Basics: An Introduction to the Types of Reward Points
  2. A Beginner's Guide to Credit Card Application Rules
  3. Beginners Guide To Credit Card Rewards: Transferable vs Fixed-Value Points

2. Saving Money

The basis of the travel/loyalty/miles/points “game” is to save money and live better. Are you like me? When I first started working my way through the field, I thought that people who worked in this space were magicians! The reality is that there’s no black magic here. It takes some time and careful study.

Miles/points should be viewed as an alternative form of currency. This is why we often discuss flexible point “currencies” such as Chase Ultimate Rewards, Amex Membership Rewards, or even the often overlooked Citi ThankYou Points.

Saving money is saving money. Some may scoff at the idea of purchase points because that's “losing the game”. But there are sometimes when it can make sense. Currently, you can buy Hilton Honors points with a 100% bonus. If you were going to pay for nights at a luxury property like those in Mexico, French Polynesia, or the Maldives, you can save over 50% off the cash rate by buying points.

For example, you could recently buy Radisson points with a 100% bonus. By buying points at that rate, you could pay $245 per night for an overwater villa in the Maldives. Wouldn’t you consider that a deal?


3. Traveling More/Better

Some people in the miles and points game need to take a step back and reassess the situation. All of us have different goals and ideals for each program. While some might want to get to Japan in first class, others may just want to save on flights for their family's next Disney vacation or trip to the beach!

If you pick up a Southwest Companion Pass or jumped on the Frontier Elite Status match I shared last year, you may fall into the latter category. Just because someone used their points or bought cheap cash fares doesn’t mean it's wrong; it's all about each traveler's priorities.

I’ve done everything from booking $10 flights for my family on Frontier all the way to redeeming miles for a $9,500 (per person) lie-flat business class tickets on ANA via Virgin Atlantic’s Flying Club program. The latter I did as a gift to my brother and sister-in-law just because miles & points made it possible!

4. Accomplishing Your Goals

While adding more cards can be beneficial, you don’t need to be Heinz with 57 varieties to succeed in travel and loyalty programs. Having a clear-cut strategy for what you want to do and how you want to get there will eliminate much of the FOMO (Fear Of Missing Out).

One of my business partners made a plan to use the extended Chase Pay Yourself Back feature to cover the cost of a kitchen remodel — it saved her $15,000!

Sure having a variety of award miles/points provides more options and choices, but there’s no point stressing yourself out collecting a few random points here or there and not having enough to complete your goals. After all, most people jump ship when they start bouncing all over the place because they don’t end up accumulating enough of the points they need to accomplish their goal.

Points & miles are similar to cash. They rarely increase in value and are subject to becoming less valuable over time due to inflation (of costs). Think of it just like a savings account. If you don’t save up for your next trip, you’re either going to have to cancel it or borrow from somewhere else.

5. Having Fun

Don’t worry about what everyone else is doing, work out what you want to do personally or for your family. Are people still laughing at me for picking up Frontier’s Elite 100K status? Probably. And I don’t care because it helps me to do more of what my family loves for less. If we can make earning and burning award points/miles fun and rewarding, all while saving your hard-earned cash, that’s the real goal.

However, if you’re ready to step up your game a bit, check out Award Travel 201 ($89.99 annual fee which comes with complimentary AwardWallet Plus). We won't beat you over the head to maximize to the extreme, but we are building a community of people who love to travel and are interested in putting a little more time, effort, and research into the programs.

How do you define winning in travel and loyalty?

5 / 5 - (5 votes)
AwardWallet Tip of The Day
Did you know that you can track loyalty accounts and travel plans for your entire family with one AwardWallet account? Simply add your family members and then add their programs to AwardWallet.
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  • Thanks for this article. Yes, I agree. the first thing is to travel more and have fun!

  • Great post! Love point number 4 especially, regarding accomplishing goals. It’s very personalized at the end of the day, so as long as we accomplish our goals, it’s a win in my books!

  • amelia grecco says:

    Great post, i totally agree about the fack that miles saving is the way to go… at least for those of us that think traveling is an investment not an expense!.
    Of course you have to give it some time to study the sistem and what its best for you, as with any other investment.

  • Hello, in South America it does not cost more to get to buy miles and the time that they last without expiring is short, would not the miles that you buy have no expiration?

    • The same expiration rules apply to miles that are purchased versus one’s that are earned by flying. Each program has it’s own rules and ways to extend the expiration that one should be familiar with in order to be safe.

  • Yes, I agree.
    The first thing is to travel more and have fun!

  • I just wish I could build the larger amounts faster and I can’t do that without bonuses and spending money.
    I think that if you can get most of your trips covered one way or another it’s good to take the time. Why not? My brother doesn’t earn anything towards travel and I just don’t get it. I like money back too but I see points and miles doing more for my family. To each their own.

    I think I win by learning new ways to earn points and miles by doing things I do anyway.

  • I would think an obvious way to tell if you’re “winning” is if you’ve learned how to make the system work for you instead of you working for the system. I grew up in a household where the use of credit cards was an absolute last resort; as such I never would have learned all the ways I can make my cards help me reach my personal goals without learning how to maximize my point-earning potential through these blogs. And while it did take a lot of effort at first, I don’t even think or stress about how many times I swipe my credit cards because I always pay them off before the bill even comes in, and my credit score has improved as an added bonus 🙂

  • If you are using your points in a way that makes you happy, then you are “winning.” Enough said.

  • Tara Chavez says:

    These points seem to be burning a hole in my pocket…and yet the last vacation I took was nearby and using No points for an airbnb.

  • I’ll add one more thought; points that are subject to devaluations (Wyndham, JetBlue, etc.) I relegate to the “travel more” column, since they’re earned/burned quickly, whereas transferable points (Chase/Amex) are used for “travel better”, since I can sit on them much longer while saving up for a major redemption, and the points are better suited for that use.

    I committed to one airline and one hotel chain which make sense for my situation, and earn transferable points everywhere else for maximum flexibility. “Having fingers in too many pies means you’ll never get a slice.”

  • I must say that Chase helps folks in North America win with its extensive loyalty card offerings.

  • “How do you define winning in travel and loyalty?”
    1) Every trip abroad over the past 15 years has been in First or Business, booked with reward points, usually transferred from Amex or Chase, because I charge every expense in life and business I possibly can to those cards, and in the multiple points per dollar spend categories as much as possible. Yet, I still end each year with more points than I began the year, even after redemptions, across Amex, Chase, Diners, Alaska, American, Delta, JetBlue, Spirit, United. I love flying and travel – security requirements and crowds (people watching) are just part of the shared experience.
    2) Usually have had multiple great saver itinerary redemption choices for each award trip taken, because of multi-airline credit cards and the 6 major airline programs in 1) above.
    3) Competitively bid all domestic flights (and international costing less than $500-$1,000), using Google Flights, to keep the price as low as possible, almost always in the extra legroom economy section, or First Class/Biz Class/Big Front Seat (Basic Economy for 1 and 1/2 hour flights if my luggage can fit under the seat in front of me), for less money than most flights same route same day charging for un-upgraded Basic Economy. And earn 5X or more points in both the airline programs AND Amex Platinum. Some level of priority boarding comes at no charge with all my tickets, except Basic Economy. Have not once been stuck in a middle seat or unable to bring a carry on over the past 15 years.
    4) ALL flights, award or cash, always booked directly with the airlines or occasionally Amex or Chase, never through any “grey market” or other 3rd party channels.
    5) Booked all hotel stays through airlines (usually Alaska) to earn bonus airline points, except Hilton and Marriott because Amex Platinum provides Hilton and Marriott Gold Elite status (so earn hotel points in those 2 programs).
    6) A variety of business lounge experiences before almost every flight (and during layovers), domestic and international, including broad tarmac views, outdoor observation decks, hot shower before my connecting flight, fast free wifi, and global cuisine (buffet or table service), either as a perk of the award flight ticket, or Amex/Chase lounge access, or lounge day pass covered by Amex Platinum $200 annual airline fee credit (American as the chosen airline).
    7) Pay all credit cards in full every month.
    8) Am nearing retirement, so the stash of points will be good for (hopefully) increased travel.
    9) AwardWallet makes it fun and painless to keep up with all the points and expiration dates and login credentials, as well as check which card will earn the most points for merchants I plan to buy from.
    10) Periodically review my card portfolios to minimize annual fee cost without sacrificing benefits I actually use, so my current annual fee cost is about 2/3 of the highest it ever got.

  • 1-2-3-4-5… check, check, check, check, check. Hey, I think I’m winning! ?

  • Yup, we started with this sometime back. Didn’t even know about the perks of mileage programs and now are discovering more. Thanks for this article because we were not aware of these perks 🙁

  • Thanks for a fun article. I agree that it is often what works best for you and your family.

  • Bill from Maine says:

    I know I’m winning every time I land in a destination that I would have never seen without points and miles.
    I was watching Wheel of Fortune the other night and the winner received a trip to Italy valued at $9K. I can do the same thing signing up for a couple of credit cards and in many cases not having to worry about paying a huge tax bill.
    My strategy is easy. Obtain elite status in the programs I value and travel to where I want using points and miles.
    Credit card signup bonus’s have to be the easiest way of enabling a person to accomplish this.

  • There might be some best practices to be aware of, but at the end of the day, there’s no one-size-fits-all answer.

  • HeavenlyJane says:

    6. Your credit score keeps getting better.