Rebuilding from scratch: My elite status and travel strategy for 2020

Dec 24, 2019

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With 2019 drawing to a close, I’m evaluating my elite qualifications for the year, and figuring out my strategies for travel and status in 2020.

This has been a really fun year of travel for me. Unfortunately, it’s been a little bit less exciting on the status-earning front. By December 31, I will have been on 95 flights spanning almost 150,000 miles this year — one flight more than last year, but about 50,000 miles less. The difference primarily came from mostly traveling domestically rather than internationally. About one-third of those flights were on United, one-third on Southwest and the rest were a mish-mash of flight reviews, budget airlines and other options that got me to where I needed to go, such as Royal Air Maroc to Liberia for our 2019 PeaceJam conference.

For further context: I’m single, and don’t have any kids (or pets) to consider when I travel. For my personal travels, I spent just over $4,000 on airfare this year, including taxes and fees on award flights, and around $3,500 for all of my lodgings this year (outside of a sailing trip). I almost always fly economy unless my upgrade is complimentary, and I’ve splurged on fancy hotels — even on points — a mere handful of times in my life. I’m a destination over journey kinda person (working on that), so as a general rule, I’d rather travel more with my budget than blow it all out on a few big things.

With my travel philosophy out of the way, here’s where I stand status-wise with each travel brand, going into the new year:

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In This Post

United Airlines: From Premier 1K in 2019 to Silver in 2020

This one’s going to hurt: I’m dropping from Premier 1K to Silver on United on January 31, the day after my birthday. As you can see from the screenshot above, I’m significantly short on both my spend and segments flown after United significantly increased requirements for reaching top-tier status in 2020. Since I use points for a good chunk of my own travel, I’m definitely not chasing United 1K any longer.

At the beginning of the year, I consistently received complimentary upgrades to business class on domestic flights, since my 1K status rolled over from 2018. But that changed toward the middle of the year, as business travelers began building up their 2019 elite status and my upgrades stopped clearing.

Related: What is United elite status worth?

It’s been really nice having top-level status for the first time in my life over these last two years, and it won’t be my last time. Personally, the difference between 1K and Platinum, the next level down on the status hierarchy, was very noticeable for me. The perk I will miss the most is my access to the dedicated 1K help desk staff, who unfailingly provided prompt, helpful service by phone and email.

I usually fly United/Star Alliance because the network has the widest range of flights to the destinations I visit the most frequently, which includes Taiwan at the top of the list. I’ve logged 260,000 lifetime miles on United, and am waffling between spending the next two decades (!) inching toward Million Miler status, or ditching my sunk-cost fallacy mindset and defecting to Delta instead. 

No matter what, I’ll continue to use and earn United MileagePlus miles for award flights; I use the MileagePlus X app religiously, primarily for Alamo Drafthouse gift cards, which helps me maximize every dollar I spend with participating merchants. And Chase Ultimate Rewards transfer directly to United. I’m currently sitting on nearly 200,000 United miles, so I’m open to suggestions for a memorable way to use them!

In case anyone else finds themselves in my same shoes, I’ll pass on a few cautionary newbie mistake stories. I didn’t really know how to maximize my status, especially when it came to status matching and challenging: I screwed up my game early on by not doing a better job with matching or challenging to Delta and American.

I was offered complimentary AA Gold thanks to a targeted mailer and with Delta, I successfully requested a 90-day status match to Silver Medallion. But I could have done much better, since I wasn’t able to meet either set of challenge requirements within the designated timeframe.

In fact, with Delta, I didn’t have any say over which airline I was flying for my consulting work trips, so I wasn’t even able to fly the required number of miles within the designated time to complete the challenge to Silver. And with American, my request for a status match from 1K on United was denied because I had already been invited (and accepted) a complimentary boost to Gold for three months via that mailer.

With both airlines, it was really nice getting a taste of their premium offerings while it lasted. What I didn’t know was that most airlines have a strict rule about the number of times you can apply for a status match within a given timeframe. With Delta, for example, there’s a three-year restriction before I would be eligible to apply again.

Alaska Air is even stricter. There’s a once-in-a-lifetime status match restriction. I applied for MVP Gold 75K last year based on my United 1K status, so I can’t ever apply for a status match again. It was nice while I had it.

I recently made a Hail Mary effort to maintain my Star Alliance Gold status, at the least, by requesting a status match to Turkish Airlines based on the advice in this article. I heard back relatively promptly, within two weeks, with a polite but firm rejection. I’ve submitted another final-ditch application to Hawaiian Airlines and have been asked to send over more documentation. I have a current 1K membership that was earned from last year, but this year’s flight records look far less impressive from the perspective of an airline hoping to earn all of my aviation business. So we’ll see how that effort goes — I’m not holding my breath. 

2020 goal: Figure out the most memorable way to spend 200,000 MileagePlus miles. Suggestions welcome.

Southwest: From A-List to A-List through March 2020

Ahh, Southwest. I actually have The Points Guy and Southwest to thank for serving as my gateway into the world of points and miles. Like many newbies, I got hooked on earning and maximizing the Companion Pass back in 2012, and expanded my world of credit cards from there. I’ve been a consistent Companion Pass holder since then, and have successfully challenged for A-List status the last two years. I usually earn it by participating in the status challenges that Southwest offers every so often — these usually call for targeted travelers to fly six Southwest flights within the next 90 days.

I won’t lie: I’ve learned to love Southwest a little bit less after tasting the sweet bougie-ness of having top-level airline status. It’s nice getting the rush of complimentary upgrades to business class, lounge access, free booze and everything else. But Southwest still does a darn good job of getting me where I want to go, how I want to get there. I don’t often check bags, but it’s really nice not having to second-guess how much status I have (and if it’s sufficient for a free checked bag), if it’ll expire on my trip and force me to pay for my checked bag on the return leg.

And of course, I never worry about change fees with Southwest; in fact, when I book with points, I don’t even have to worry about canceling my flight to get a refund — if I no-show, the points are automatically returned to my account. Of course, I make every effort to cancel as a courtesy when I know that I won’t make a flight; it frees up the airline to offer my seat to another customer a little sooner, after all. But it’s nice to know that in the event of an emergency, I don’t have to add “hop on the phone with customer service to cancel my flight on a time crunch” to the list of tasks I need to check off.

One way I use Southwest for maximum value is by using my stash of Rapid Rewards points from earning my Companion Pass each year to position myself for other, more aspirational flights. I live in Texas, and many of the best international cash and awards flight sales originate out of major coastal cities such as New York, San Francisco or Los Angeles. I’ll usually book myself a super-cheap positioning ticket on Southwest from Austin to New York or California, then pay cash or points for a round-trip international flight from that major city to my destination.

Related: What is Southwest elite status worth?

I’ve found A-List to be incredibly valuable when I fly Southwest: I’m writing this from 39,000 feet in the air on a nonstop flight from Austin (AUS) to San Diego (SAN), for example. I originally booked a different, cheaper flight for this date using my bank of Rapid Rewards points. But since my A-List status allows me to make free same-day standby requests on any other flight traveling to the same destination, I was able to get onto the flight I actually wanted to take without paying the $200 higher price difference. I’ve done this at least half a dozen times in 2019, and value this perk more highly than anything else with Southwest. The Group A boarding is a close second, however: It’s really, really nice not having to do the mad dash to check in exactly 24 hours before my flight departs.

My Companion Pass expires on Dec. 31, but I’m not in a crazy rush to renew it this time around. For one, I don’t have a dedicated companion to designate right now and second, I’m just coming back out of Chase’s infamous 5/24 restrictions, and will probably never qualify for Chase cards again after this next elaborate round of applications I’m strategizing for 2020. So I’ll apply for a couple of higher-priority cards first — I have my eye on the United Club card (business version) — before going for the Southwest Performance Business card for the 365 Wi-Fi credits included each year. Considering Wi-Fi costs $8 per day on Southwest per device, that’s a hefty value proposition in that one benefit alone.

2020 goal: A-List Preferred for the free Wi-Fi would be pretty sweet — but only if I don’t get the Southwest Business Performance card, which negates that perk for me.

Delta: Started at the bottom, now we [still] here

I don’t really fly American or Delta very often, but this year, I did travel with both carriers at least twice, so I’m throwing in a mention for both. I don’t have any Delta credit cards, and I didn’t book any Airbnbs this year (if I had, I would have done so through the DeltaAirbnb.com partnership link for bonus miles). And yet I still managed to earn 4,000 SkyMiles from everyday activity: you’ll notice above that none of my earned miles since March came from the big 3 earners — flight, hotel or card. I linked up my Lyft and Delta accounts early this year, and I use the Delta SkyMiles shopping portal when it makes sense. So as you can see, even little trickles of earnings add up over time.

2020 goal: Get an Amex Platinum and fly Delta more often. Austin has a really great new SkyClub — and after reviewing it for TPG, I want to go back again and again.

American Airlines: In the end, it doesn’t even matter

I visited TPG’s parent company, Red Ventures, for the first time(s) this year. American is the only airline that flies nonstop between my hometown of Austin and our headquarters in Charlotte. So for that reason alone, it looks like I’ll be on American metal a lot more next year.

You’ll see from the screenshot that I’m close on reaching Gold — at least in terms of EQDs — as of mid-November. But I just didn’t have it in me to squeeze in an extra 7,320 miles of mileage run (OR 16 more segments) in the final six weeks of the year in addition to the 23,000 miles of travel I had already booked between Nov. 15 and Dec. 31. So goodbye to my chance at securing AA Gold for 2020: It was nice looking at you from afar.

Related: What is AA elite status worth?

While I didn’t start or end the year with American status, there were a few sweet months in the middle. I received that flyer in the mail offering me complimentary AA Gold elite status for 90 days, with the opportunity to extend it by meeting a few requirements. I already had prior booked travel and other schedule conflicts that didn’t allow me to hit the target goal for miles flown. But for those few months, I did enjoy my complimentary auto-requested upgrades, 40% elite mileage bonus, complimentary Main Cabin Extra seat at check-in and free checked bag.

I was also given 10 complimentary 500-mile upgrades, none of which I had the opportunity to use. While holding elite status is a prerequisite for applying the upgrades, they don’t actually expire. So if I manage to hit AA Gold next year, I’ve got 10 upgrades waiting for me to use for myself — or maybe for you.

2020 goal: Earn more AA miles, especially with all of these amazing Web Specials that keep popping up. I first found out about their existence last year around this time, when my colleague JT Genter discovered amazing economy award availability for domestic and international flights. Thanks to that find, I booked an impromptu flight to Madrid for a flat 18,000 miles round trip and had a blast visiting TPG senior writer Lori Zaino and her amazing friends in March.

Now more and more routes are available each day, and it kills me that I don’t have enough miles to book a 45,000-mile business class flight to Tokyo, for example. So I’ll probably apply for the CitiBusiness® / AAdvantage® Platinum Select® World Mastercard® sometime in 2020, because it offers 70,000 American Airlines AAdvantage® bonus miles after spending $4,000 in purchases within the first 4 months of account opening with just a $99 annual fee (waived for the first 12 months).

That rounds it out for my domestic airlines flown this year — let’s move on to hotel loyalty programs.

Hilton Honors: Diamond is this girl’s best friend

Aiight. See that status above? I hold it solely because I have The Hilton Honors American Express Aspire Card, which comes with Hilton Diamond status for as long as you are a cardholder. I almost never stay in chain hotels unless it’s for work, and TPG books a lot of our travel on points, while our parent company, Red Ventures, books most of its employee travel via third-party agencies, so most of my stays don’t qualify for points. But still, being Hilton Diamond is sweet, especially for a budget-travel plebeian like myself.  

Related: How to choose the best Hilton credit card for you

I’ve actually been a proud owner of the no-fee Hilton Honors card for several years. This summer, I was randomly targeted for an upgrade to the Aspire. The offer was too good to refuse: Upgrade my existing Hilton card to the Aspire without triggering an additional credit pull or card application, earn 150,000 Hilton Honors points once I hit the same spend that’s required for regular card applications.

Related: What is Hilton elite status worth?

The annual fee of $450 is pretty steep (see rates and fees), but there are many other valuable inclusions such as an annual Hilton resort credit of up to $250; up to $250 yearly credit on airline fees; and a free weekend night when I opened the account, as well as each year on my card anniversary. 

2020 goal: Book myself a really aspirational stay with all those Hilton points. I’m thinking overwater. I’m thinking a week, minimum. I’m actually really inspired by TPG director Summer Hull’s recent Conrad Bora Bora vacation, so maybe I’ll just copy her and stay there. Like Summer, I also canceled a big Marriott reservation earlier in 2019, and I agree that Hilton (plus my Diamond status) may be the right chain to house me in paradise.

Marriott Bonvoy: Not all that glitters is gold

2016 was a big year on the points and miles front. Marriott acquired Starwood, and everyone paid attention. Amidst the many ups and downs over the next three years, I set my sights on booking a sweet-spot award reservation at the St. Regis Maldives and clumsily crafted a strategy around my goal, which included applying for the Marriott Bonvoy Brilliant™ American Express® Card when it launched in summer 2018, which is how I have my Gold Elite status.

Very very long story short, I achieved my booking goal, but ended up not going to the Maldives this past November; instead, I canceled my rezzie and went to Liberia with TPG and PeaceJam. So now I’ve got all of these points, and no particular plan in mind yet for where I’m going to spend them.

It’s been difficult to keep up with all of the Bonvoy developments this year, and my interest in the program has waned somewhat as a result. As the kids might say, I like Marriott, but I don’t know if I like-like Marriott. That being said, I had an extremely memorable stay at the Ritz-Carlton Abu Dhabi in November 2017, which was ranked as a Category 4 property back then (it’s now a Category 5). I can find similar-caliber hidden gems in the new Bonvoy portfolio, especially at off-peak pricing, I’ll be a happy woman in 2020.

Related: What is Marriott elite status worth?

2020 goal: Similar to my Hilton goal, I want to find a fun, aspirational property for my points, maybe for a group trip with my friends. I’ve never sat on this many hotel points before, and while it’s small potatoes to some, it does represent a few years of dedicated earning for me. Since it’s a bad idea to stockpile points without a specific goal in mind, looks like I’ll just have to book a vacation.

Hotels.com: From gold to cold


I’ve tapered off on Hotels.com bookings this year for multiple reasons, since most of my work travel is now booked through TPG or by our parent company. That being said, I still utilize this site for smaller bookings, such as my upcoming New Year’s stay in Chiang Mai. My reward night value hovers around an average of $114 or so, but that’s still a nice little discount, especially for a “splurge” destination in a budget-friendly country like Thailand.

2020 goal: Nothing. Based on current trajectory, I won’t reach Gold again any time soon.

Related: My Target REDcard gets me 10% off Hotels.com bookings

Airbnb: Belong anywhere

There isn’t really any elite status to earn on Airbnb, but it’s a big part of my travel strategy. I love it for trips where you want to spend quality time together but still want your own space at night. There are a number of times when Airbnb just makes sense, and large groups traveling together is one of them. This summer, a dozen friends and I, including one toddler, shared a lake house which included a deck, kayaks, a massive kitchen and patio and ample beds for all of us for just $270/night.

TPG contributor Brian Biros would agree with me: In 2018, he and his dad worked together to get 24 people from his extended family to Puerto Rico for a massive family vacation — a feat possible thanks to two huge Airbnb rentals in the same neighborhood.

That being said, I don’t really roll with a large crew very often; my travels actually skew heavily in the opposite direction. You can see from my screenshot above that I really, really love staying in quirky little houses in New Orleans, for example. There’s something uniquely authentic about experiencing a new place in such a hands-on way, and the experience is especially poignant in places like New Orleans that are bursting with history and culture.

2020 goal: I still have $1,000 credit to spend from 2018’s Black Friday deal on the Google Pixel 3/3XL, so my goal for 2020 will be to use that up somehow.

Related: Here’s how to become a superhost on Airbnb

Hyatt: Discoverist

There’s one brand I’m interested in exploring further in 2020, and that’s Hyatt. I have limited exposure to this brand, which makes sense: Hyatt only has 875 properties worldwide as of the company’s last count. But each touch I’ve had with a Hyatt property has been pretty enjoyable, and many of my coworkers at TPG speak very highly of their experiences with the brand.

I’m game for a new game, so I’ll probably start by signing up for The World of Hyatt Credit Card, which will automatically grant me Discoverist elite status again, which I currently hold through Feb. 29, 2020 thanks to my [recently downgraded] United Club credit card. And if I want to book a Hyatt stay in the meantime, it’s super easy: My Chase Ultimate Rewards points transfer over instantaneously to Hyatt on a 1:1 basis.

Related: What is World of Hyatt elite status worth?

Anything new for 2020?

As of right now, I actually have exactly zero trips planned or booked for 2020, other than my return flight from visiting family in Asia in mid-January. One of my best friends is getting married in Maui in September, so I’m mentally planning for that — but flight sales to Hawaii have been abundant this year, so I’m not too worried about getting a good route there and back.

This isn’t the coolest admission for a TPG employee, but I’m planning to travel significantly less next year. Instead, I want to focus on making each trip as meaningful as possible. For example, I have just one more continent to visit before I check off all seven, and you can probably guess which one it is. If I find a good deal to Antarctica via any of the major routes, you betcha I’m going to book it.

In 2020, I also want to be present as much as I can, when I can. These last two years of travel have spanned almost 350,000 miles, but truth be told, I don’t honestly remember a lot of it. Highlights stand out here and there, but I spent a lot of my time and attention on maximizing, double-dipping, triple-stacking and strategizing. But when I think back over the last two years, a lot of those “non-status” moments stand out the most: Frying chicken with my friends on that lakehouse patio, sharing my companion pass with the people I love, sailing in the British Virgin Islands with a friend who sails, traveling to see my brother in Portland and crashing on his couch for a week. None of those earned me a red dime toward elite status, but they’re the ones that make me feel the richest.

…That being said, I also greatly enjoyed my Ritz-Carlton Abu Dhabi experience, and running up and down those marble stairs to get to my 600 sq. ft. suite of rooms was also a highlight I’ll remember forever. It’s all about balance, y’all.

For the rates and fees of the Hilton Aspire card, please click here.

Featured photo by Katherine Fan/The Points Guy.

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