After My First-Ever Upgrade On United Airlines, I Was Hooked – And Did Crazy Things To Stay Up Front

I flew what seemed to me like a lot growing up. My parents were divorced and lived on different coasts, and I went back-and-forth. And living in New York I naturally found myself in Florida over winters as well. (My very first flight memory is a drive to the airport for a flight to Florida, probably when I was three.)

But I always flew coach, and I remember thinking to myself as I boarded a widebody flight once that I would always travel in back. I’d never be wealthy enough to sit up front, and even if I was why would I waste my money that way? I had no idea what it cost, but it just seemed so… extravagant to be more comfortable for a few hours.

Of course first class was much more expensive, even 20 years ago. And domestically premium cabins were mostly filled with upgraders and nonrevs. Airlines have learned to manage their first class inventory and sell more seats at a discount, in order to make more money.

Once I graduated college I started traveling for work and quickly earned Premier status on United Airlines. When I learned that meant I was eligible for upgrades I got excited. My first trip as a Premier member of Mileage Plus was a roundtrip Washington Dulles – Los Angeles.

  • The outbound was a Boeing 767 on Thursday around 5:30 p.m. Good luck getting upgraded! But I didn’t understand upgrade priority, I just hoped there would be an unsold seat – because it would go to me! I was nervous all day from lunch onward, sure I’d get to experience first class for the first time. I did not.

  • On the return, though, I did clear the upgrade. It was amazing. I had a business class recliner on a Boeing 777. Lunch began with an almond-dusted shrimp appetizer, followed by steak. I had a couple of cocktails, read the Sunday New York Times, and genuinely did not want the flight to end. I was hooked.

After that upgrade I learned how to play the system so that I’d get upgraded, at least on long flights, as a lowly first-tier Premier elite. If I needed to go cross country, I’d depart at Noon on a Wednesday. Via Denver, rather than taking the non-stop which had more premium demand. I avoided flying between 7 a.m. and 9 a.m., and between 5 p.m. and 7 p.m. which were prime business travel times and meant more elite competition (and the occasional paid first class ticket taking up seats).

I was always searching for widebodies with more premium seats. Needed to fly to Phoenix? I’d go Washington Dulles – Los Angeles and backtrack to pick up a 747 for the long flight. And I’d start in Baltimore, taking United’s Jetstream 32 turboprop Baltimore to Washington Dulles. That accomplished (3) things:

  1. Airfares were lower out of BWI, and often didn’t involve Saturday stays
  2. I checked in earlier, which put me higher on the upgrade list if I needed to clear at the gate
  3. I’d earn more miles and an extra flight segment.

At first I never actually flew first class on a long flight, I always flew business. Business class on a widebody was better, but it didn’t sound better. I was so excited when I checked in for a Washington Dulles – Los Angeles – Phoenix trip and the agent offered to put me on a Boeing 757 for the Phoenix non-stop. It wasn’t as good a seat but it was first class and I got an ice cream sundae dessert.

The first time I ever flew three-cabin first class was 23 years ago on a United Chicago O’Hare – Detroit segment when the airline swapped an Airbus narrowbody for a Boeing 767 the day before travel. I saw my seat assignment disappear, called up and asked to be seated at the very front of the cabin, and then found myself the only passenger in ‘international first class.’ It was just an hour and a quarter but it was glorious.

I’d gotten hooked on miles even before that but hadn’t yet realized miles could be used for upgrades confirmed at booking. I was earning miles left and right, getting my account statements in the mail and following the promotions like a dining offer of bonus points for 3 participating restaurants (you earned 10 miles per dollar on all restaurants then, and that particular promo had no minimum spend so I topped off the required restaurants with a soda at a Chinese place).

Instead I funded my upgrades by buying paper 500 mile upgrade certificates on eBay at a deep, deep discount. I later learned to confirm upgrades back when it was just 10,000 miles at booking one-way. (Alaska Airlines charged just 5,000 miles for a confirmed upgrade, and had started flying transcons – and their upgrades came out of revenue inventory until 2022).

I also learned that if I could buy upgrades on eBay, I could sell them there too. I wasn’t making much money and I used to fund my weekends by signing up for US Airways and America West small business accounts. The welcome kits came with upgrade certificates, which would bring $50 – $100 apiece. I was hooked!

And that’s why over the years I’ve been dumpster diving for Wendy’s soda cups, shown up at hair restoration consultations, and more, all so that I could travel more and more comfortably than I’d ever thought possible.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. Who knew you didn’t know the premier benefits before you earned the status!

    I knew of upgrades, but thought they were limited, needed the 500 mile certs, etc didn’t realize some of the programs (not UA/AA) had ‘unlimited’ no sticker upgrades, and that got me hooked on chasing status. Whether it was the better route or not hard to say.

  2. Nice background. Best upgrade story was my grandson.
    He and his mom flew Delta from JBerg to LAX via ATL. Overwater they were business. Checking in for the LAX flight, both gold and Delta offered the only upgrade seat left to my grandson.

    His mom walked him to the counter and asked the agent if they would walk him on or should she take him on.

    Said the look on the agents face was priceless when they realized they had upgraded a 2 1/2 year old kid.

  3. Growing up, my family actually lived abroad for a few years in England. My dad wasn’t military, just finance, and at that point in his career he was working for TRW Space and Defense, now part of Northrop-Grumman. They needed a controller for a plant over there in the automotive division.

    I grew up in California, so moving over there, we’d do the 11 hour LAX-LHR in an American 767 at regular intervals, at least a few times / year until moving back. I was 10 at the time. I also did my first international solo trip the summer after moving back, at 13, in order to go visit my best friend over there, with whom I’m still in touch to this day. Travel really does connect people…

    (I’ve also been an AAdvantage member since 1997 as a result of all that. Almost certainly not the longest here, but probably above the median. Also maybe a little noteworthy considering I’m only in my mid-30s now.)

    Anyway, I remember having the exact same right as you, Gary. Every time we’d get on an international widebody, we’d file past first and business class. I’d think how cool it’d be to sit up there – the seats were all recliners back then, even in first, but 12-year-old me was still in awe – but it probably wasn’t in the cards for me.

    Anyway, one of those trips while we were over there, we were delayed going from NCL-LHR and misconnected. My dad argued with some American or BA rep for a while. I don’t even remember him raising his voice, which would’ve been unusual, historically the men in my family have tempers. But he got us out via a reroute to CDG. We didn’t know what was happening until we boarded the final segment in Paris, we were happy just to be on our way, and he kept it a surprise even for my mom I’m pretty sure. But somehow with that rerouting, he managed to get us interlined into Air France business class (!), on a 747 (!), for the TATL segment.

    The bread basket, full of warm French pastries, like they just came straight from the boulangerie… I’ll never forget it.

    (Of course my first international premium trip that I got for myself and that wasn’t the result of a mishap, that didn’t come until much later, as an adult.)

  4. Unfortunately premier status generally doesn’t get you upgraded on long haul international. I learned the hard way en route to Uganda watching over 15 seats in business class not get upgraded as I had gold status.

  5. Nice story!

    I also got my first taste of business class about 12 years ago while flying to India for my wedding on Qatar airways where with my paid economy ticket I was bumped to business class for the JFK to DOH leg because a family wanted to sit together on a full flight. Got spoiled after that experience and since then has become a second job to make sure can always sustain never having to sit in the back on any long haul flights so got heavily into the points game!

  6. What a beautiful read! Thanks for sharing. More content like this please, we’ve seen enough of the FRA-JFK SQ suites of late lol

  7. Gary,

    I do not know if this is one upping you or not.

    My first ever upgrade was from DCA-MSP-MKE. I’d take the long way (instead of via DTW) just for the heck of it in my college days. Somehow, I managed to accrue 10,000 BIS miles from actual flying — and realized I had enough for an upgrade. So I took it, because I had no idea what else I was going to do with those miles… surely I’d never actually get enough for a free ticket.

    The funny part with that particular upgraded ticket was that DCA-MSP was a DC-9, but MSP-MKE was a DC-10. That was my first time on a wide body, and an upgrade to boot! Two things struck me: 1) That was an awesome upgrade, but 2) Why did they run that flight on such short route?

    Shortly after those days, I moved out to LA. I worked midnights back then, and for whatever reason it was actually pretty easy to get Platinum out of LA. (They were running lots of double EQM then.) I managed to snag platinum for two of those years. My upgrades (working midnights, you weren’t flying with the road warriors) pushed 100%. The few times they didn’t, I had a reserved bulklhead seat. It was actually a pretty sweet deal — and I had no idea why it made financial sense to the airlines to upgrade my broke ass like that 😉

  8. Since I read your articles, I have always seen you as an accomplished businessman, spoilt by your parents, then by your company : your itinerary seems quite different ! It makes you much more human, if I can say that in my hesitant English !
    ( by the way I am so glad now to be Skyteam AF Platinum for life, after similar acrobatics !)

  9. Fun story to read mainly because I had a similar story that also got me hooked on working the FF system!

    Was going to Hawaii from Chicago. Longest I’d ever flown at that point was 3.5 hours and I hated it so I knew going to Hawaii would be a big test.

    This is where I first learned of different ticket categories. Specifically, a Y-UP fare got me upgraded to First. I scored that upgraded at a reasonable cost and never looked back I’ve been a mileage and upgrade junkie ever since

  10. Fun times. My first upgrade was a non-status gate agent random upgrade on TWA between MSY-MCI on a late afternoon trip after a job interview in the mid-’90s. I really think I was upgraded because I had a nice suit on and the first cabin was half empty. The best part was that the first-class FA wasn’t very busy and sat next to me and chatted for most of the flight so maybe that “suit magic” worked on her too 🙂 I was hooked after that but it took years to work the game. I never did get in on Wendy’s cups but my brother and law put me on the 100-mile certs on the back of Kellogg’s cereal boxes at one point.

  11. I wish I could remember my first flight, but I’m guessing it wasn’t until I was college age. My first premium class memory was a return flight on Air France from CDG. We had coordinated with my wife’s parents and spent some time in Paris with them. Her mom returned talking about the unpleasant airport experience on the return. We, on the other hand, were First Class. I think we took an elevator to a separate check in and lounge. I was floored by food offerings. We didn’t share that experience with her.

    Fast forward 40 years and we’ve got 3 recently married children and one nearly married. We are spread across 4 cities including international. I have a small business and accrue a massive number of points via sign up bonuses and spending.

    I love my role as family travel agent. So far I’ve booked nearly 500 round trips and over 500 hotel nights with points. (Yes, I have a spreadsheet.)

    I’ve been reading Gary, a few other bloggers, and Flyertalk for 10? years. Thanks to all who share their knowledge. I’m obsessed.

  12. Didn’t realize until now that your flying days got a boost because of the parents divorcing. While I’ve long seen kids flying a bunch because of separated parents, just didn’t realize that you were part of the flow.

    Were a lot of your flights as a kid done as an UAM? If so it would be interesting to hear your take on the differences between being UAMs then and being UAMs now.

  13. Gary, do you have any pictures of your experiences on those 767s/777s from way back when? Would be fascinated to see them if so!

  14. @Sam I don’t have photos from the mid-90s, but the same seats were still being flown into the mid-2000s and I do have photos ~ 2006 for sure.

  15. @GUWonder – I did fly as an unaccompanied minor, but when I was a little older, when I was 7 I remember my dad flying Los Angeles – New York to pick me up and we flew back New York – LA.

  16. Thanks for posting this Gary.

    I appreciated your candor and sense of humor, and particularly enjoyed the walk down memory lane as a fellow longtime travel hacker who’s roughly your age.

  17. Started out mostly with intra-East Coast US flights and US-Europe-Asia and back as an infant/toddler. Always economy class as far as I can remember for my pre-teen years. First time I ended up in a premium cabin domestic flight was on a NW flight out of DCA while in my upper teens. First times in premium cabin long haul flights were due to oversold or other IRROP situations on NW, KL or SQ between my teenage years and turning 20 or 21. Hadn’t arrived at an airport knowing or expecting to be in a premium cabin until around the same age as Gary got UA Premier status.

    My first airline elite status was on Delta Air Lines but it came later than it should have. I probably had dozens of DL FFP accounts since I seemed to use a new number for each trip for many years. But the airlines on which I should have gotten status first probably should have been NW or AA — but there too I was lousy about managing the numbers and using them — since we flew them the most domestically.

  18. Until the past 15-20 years, I rarely flew anything but coach. Was flying AA out of SAT after a big convention, and they asked if we would volunteer to be driven to AUS to connect thru DFW to SEA. Sure, not a problem. Got surprised with domestic FC seats. Another time, was flying with my team on NWA from MSP-SEA. I went early to organize check-in and my POC (I had gotten to know her well), said something came up and disappeared. It was a Sunday morning, the earlier flight had a mechanical, and was full of cruise passengers. So, they upgauged to a widebody to get both flights onboard. She “asked” if it was ok to put my team in Biz class. “Sure, not a problem”! I got to be the hero for a day, everyone had lie-flat seats for a 3.5-4 hour flight.

  19. An early memory: My father was a doctor. We were in the caribbean, probably St. Thomas with a connecting flight in Puerto Rico. There was a call for a doctor which my father answered. As a “thank ou,” we were all put into Business or First class, whatever they had in the late 50’s.

  20. Amazing stories. My first flight was a one way DC 3 from Atlanta to Panama City when I was in high school. Back in the early 90s I traveled from Boston to ATL with a women’s group and one of the women in my group knew the flight attendant, so he offered some of us an upgrade to first class but since we couldn’t all sit together, she turned him down (for all of us). Now at age 69, it is the closest I’ve ever gotten to getting a first class seat. It looks like I should make it more if a priority. I had no idea first class was worth having or paying extra for.

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