Get Started

Learn more about Credit Cards, Travel Programs, Deals, and more.

My Earning and Burning Greatest Hits of 2020 – Strengthening Travel Freedom for the Future

This post may contain affiliate links - Advertiser Disclosure. As an Amazon Associate, we earn from qualifying purchases.

Greatest Hits of 2020

My Greatest Hits of 2020 – Strengthening Travel Freedom For the Future

The year is wrapping up several days from now.  It feels like it’s gone by slowly and quickly at the same time – is anyone with me here?  Back in the spring, it had already become cliche to say things were “unprecedented.”  That’s not a word I like to throw around often (I feel the same way about “classic”),  but our hobby has certainly seen unique changes this year.  It’s also been a huge year for reflection and appreciation of one’s health.  From a hobby perspective, though, my greatest hits of 2020 share a common theme – strengthening travel freedom for the future.  Let’s take a look back!

Paying Myself Back

As a longtime fan of cashing out Chase Ultimate Rewards, I was floored by Chase’s May announcement of the Pay Yourself Back feature.  Chase enabled Sapphire Reserve cardholders to redeem Ultimate Rewards points for 50% more value at grocery stores (and certain other transaction types).  Sapphire Preferred cardholders could achieve 25% more value, but upgrading one of my five Freedom cards to a Reserve was a no-brainer.  Long story short, it turned something I already did into a much more lucrative venture.  By simply using Pay Yourself Back, I obtained about $3k more value out of my Ultimate Rewards.  I bet many of you fared even better.

Greatest Hits of 2020

Shopping My Way

In August, the guys over at Gift Cards Galore and Frequent Miler collectively unearthed how Citi ThankYou Points could be redeemed for a variety of gift cards via Shop Your Way at 1.2 cents per point.  While some yawned at this since they maybe didn’t have use for more gift cards, I (and many others) saw value here.  For me, my redemptions were singularly focused on the gift cards of one retailer:  Walmart.  And I redeemed all of my ThankYou points at the time.  But why?

I knew that I could buy discounted Disney gift cards at Sam’s Club with a Walmart or Sam’s gift card.  The whole process looked like this:

ThankYou Points –> Shop Your Way Points –> Walmart Gift Cards –> Discounted Disney Gift Cards at Sam’s Club

Long story short, I got a value of just over 1.25 cents per point by redeeming this way.  This is right at the same ThankYou point value I would get for Disney World bookings with Citi’s Cruise and Tours Department thanks to the Citi Premier Card’s extra 25% point value.  The true win for us was increasing our travel freedom.  We can use our Disney gift cards however we want with no deadlines attached to their value, unlike committing to a specific trip.  There’s no calling Citi to book, either.  My redemption via Shop Your Way was even more vital to achieve that open-ended value since the Premier’s 25% bonus value is disappearing in April 2021.

This method was killed a few times over later in the year, with Walmart gift cards disappearing from Shop Your Way’s site, Sam’s not accepting Walmart gift cards for Disney gift cards, and the devaluation of Thank You points redemptions on Shop Your Way.  But it was very lucrative while it lasted.

Greatest Hits of 2020

Loads of Southwest Points During a Pandemic

Many airlines and hotels created new options for changes, cancellations, and redemptions due to the pandemic.  Southwest came up with one of the more attractive options for me – turning travel funds into Rapid Rewards points.  I had plenty of gift cards and travel funds with Southwest for a long time, many thanks to various cards’ airline credits.  Through a bit of a tedious, but not overly painful process over the summer, I (and some of you) turned those accumulated assets into Rapid Rewards points.  My already-healthy points balance grew much higher, and I was okay with the risks for this situation.  In summary, I did so for more flexibility and convenience in booking future flights with Southwest, my favorite domestic airline.

Amex Referral Bonuses

Taking advantage of Amex referral bonuses isn’t unique to 2020, but the volume to which I did this year is.  In years’ past, a referral bonus of 20k Membership Rewards points was big.  This year, that number is routine, and many of us saw referral bonus offers of 25k, 30k, and even 35k points.  With a bit of planning and luck with these offers, my wife and I received just over $3k in rewards.  And most of these bonuses were simply from us referring each other.

Amex has the most flexible referral offer policy out there, from my perspective.  The referring cardholder can obtain their preferred Amex credit card rewards currency (Membership Rewards, cash back, or airline miles/hotel points) regardless of the card the individual referred chooses.  There are caps, but you have separate capacity to refer from each of your Amex card accounts.  Reflect on your situation and determine what free points or money you can easily obtain with Amex!

American Express has offered excellent everyday rewards in 2020.

The Growth of Everyday Rewards – Greatest Hits of 2020 (and Beyond?)

Everyday rewards, what I creatively call any rewards I obtain that aren’t directly related travel, have been increasing for years.  These rewards grew by leaps and bounds in 2020, much of it due to the new options from card issuers during the pandemic.  While I’ve focused on these non-travel redemptions previously, I became even more focused on their utility this year in further cutting my expenses.  Indeed, why should I (or anyone else) focus solely on travel rewards?  I’m very interested to see how this rewards space develops (or not) in the coming year.  While we collectively look forward to hitting the road in the near future, I think many have grown accustomed to the everyday perks of these cards.  Will issuers continue to provide these non-travel benefits, or revert back to their pre-pandemic structure?  I’m betting and hoping for the former.

Citi Convinces Me to Hoard, Twice

In the spring, I described my plans to hoard ThankYou points.  But I subsequently obtained a far superior redemption due to Shop Your Way as I described above.  A combination of events has led me to hoard ThankYou Points (again) this fall:

  1. The death of my preferred Shop Your Way redemption for Disney Gift Cards.
  2. Citi enabling 3x ThankYou points earning at grocery stores starting in the summer.
  3. Citi removing 25% ThankYou point bonus value from the Premier card effective April 2021.

Since #1 happened, I’ve been feverishly hoarding ThankYou points from my Premier, Double Cash, and Rewards+ cards with plans to redeem them all by April 2021.  How will I redeem?  I’m exclusively redeeming for Disney World tickets in order to maintain flexibility and obtain optimal redemption value.  The big, outstanding question is what my future with Citi will be after April 2021.  What am I going to do?  I currently have no idea, but I plan to write about it here soon.

Greatest Hits of 2020

Greatest Hits of 2020 – Conclusion

Annually, I read articles stating some version of “the points and miles hobby has been different this year.”  I feel like that’s lost meaning with every passing year.  But indeed, the common theme is that the hobby is constantly evolving.  How do we evolve to stay with, and hopefully ahead, of it?  That’s the fun part, and I enjoy interacting with and learning from each of you along the way.  I hope your 2020 hobby accomplishments have been fruitful and that they will improve in 2021.  What have been your greatest hits of 2020?

Disclosure: Miles to Memories has partnered with CardRatings for our coverage of credit card products. Miles to Memories and CardRatings may receive a commission from card issuers.

Lower Spend - Chase Ink Business Preferred® 100K!

Chase Ink Business Preferred® is a powerful card that earns 3X Ultimate Rewards points in a broad range of business categories on the first $150K in spend per year. Right now earn 100K Chase Ultimate Rewards points after $15K $8K spend in the first 3 months with a $95 annual fee.

Learn more about this card and its features!

Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.
Benjy Harmon
Benjy Harmon
Benjy focuses on the intersection of points, travel, and financial independence (FI). An experienced world traveler, husband, and father, he currently roams throughout the USA close to expense-free. Benjy enjoys helping others achieve their FI and travel goals.

Responses are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.


  1. I have gotten back thousands from Chase Sapphire Reserve “Pay Yourself Back.” Wonderful way to reduce cash outflow. And if Chase stops allowing my wife to transfer her points to me, we always say, “It was fun while it lasted.” Then you tell us about a new ‘deal’ to pursue if we still want to stay in the game. I find it surprising when I tell people that I just saved $4,100 on new flooring from travel hacking. If they respond, they say something like “I need to learn more about that” but then never ask. Maybe I have a damaged DNA that makes me interested in the fun of this game.

    • Thomas,

      Thanks for chiming in. I can identify with you. This hobby works out best for me when I focus on “rewards”, not just “travel rewards”. Why limit ourselves?

  2. I am on the other end of the spectrum and keep my points to get outsized rewards I probably would not spend money on myself. Therefore I hold the points, or move them to someplace else to get the outsized reward. With many of our MS ways gone for the average guy I think points are even worth more now.

    About the only way I would cash points out is if the stock market showed me an excellent upside.

    I don’t blame anyone for cashing in points. We are all different and that is a good thing.

    • Byron,

      Thanks for sharing! I’m a cashout fan, but hoard some other currencies, as well. I throttle more either way based on need. I agree that everyone’s different and should have their own strategy.


Please enter your comment!
Please enter your name here