I think it’s useful to share my mistakes as well as my successes. One thing I’ve learned is that for people to take advantage of the offers right in front of them it needs to seem achievable. Even when I’ve been willing to walk work colleagues through everything start to finish I’ve heard people talk about travel all over the world in premium cabins as “a Gary thing” as though there’s some magic difference between us.

I’m far from perfect and exposing that may also help show that it’s all a learning process, trial and error, and that it doesn’t take anything other than being human and paying attention to improve your travel skills and jump on deals that come along.

I failed to earn miles when I was younger, even failed to have an account when I first flew enough to earn elite status. I’ve let miles expire. And I broke some program rules two decades ago without even realizing it was a big deal. These are stories I’ve shared before but not in any kind of systematic way in a couple of years.

My High School and College Miles

I debated in high school and at the start (and then the very end) of college, and saw some success at the national level. I should have been earning points. I wasn’t.

As a high school debater travel was mostly driving in-state — though I did fly to North Dakota for Nationals. We waited too long to book our tickets and couldn’t get flights into Fargo, so we wound up flying Northwest via Minneapolis to Grand Forks, North Dakota and driving. I just remember feeling like we were at ground zero in the event of a Soviet pre-emptive nuclear strike, because of the likelihood of nearby missile silos. It’s strange the things you thought of back then. Boris Yeltsin had stood atop a tank months earlier but I don’t think that had yet changed everything I had heard growing up as a kid.

We stayed at the Madison hotel in Moorhead, Minnesota just outside of Fargo. J.J. Walker was performing in the lounge. But I wasn’t aware of any points opportunities. Many of the hotels we stayed in didn’t have loyalty programs then and I certainly wasn’t aware of them.

I signed up for my first frequent flyer program as a teenager before a trip to Australia. I flew American Airlines to Sydney via Honolulu and earned almost enough miles for a free domestic roundtrip award. Those miles ultimately expired, unused.

My freshman year of college I debated for UCLA, and that started out as a phenomenal experience. The team had won CEDA nationals the previous year. They were ultra-competitive, and the work ethic was intense. I soaked in tremendous learning.

Driving back from the UNLV tournament during the winter quarter several of my teammates were involved in a van crash. (I was driving my own car just a little behind that van.)

My partner through much of the season was killed. That cut short most of my own debating, but I did continue to travel a little bit for competition and I traveled as a coach.

I went to CEDA nationals at Towson State University in Maryland my freshman year anyway and did well (without much in the way of materials, our boxes were destroyed in the crash) that was for the most part the end of my debate career. I did compete successfully in parliamentary debate in a national tournament at the end of my senior year at the University of Alabama, Tuscaloosa (I lost the final round), the only time I competed in that event. But I only flew to two tournaments as a college debater after the crash.

My last three years of college, though, I coached high school debate. I had been a member of a reigning national championship policy debate team, and though our season was cut short I did manage to learn some things along the way that let me offer some skills and strategies to students. My senior year of college the team won the California state championship.

I took my high school teams to tournaments out of state. I mostly remember driving 15 passenger vans rented from Enterprise, and staying at hotels that didn’t award points. And didn’t have interior corridors. There weren’t that many points to be earned, but surely I’d have benefited from crediting flights to a frequent flyer program.

Debate today is far more electronic than it was then. I recall carrying a Mac onboard flights in 1992 and 1993. And I couldn’t imagine paying checked bag fees for all of the tubs of ‘evidence’ we used to carry around on carts. It’s a good thing airlines didn’t charge for checked bags in those days.

My senior year of college I easily flew enough to earn elite status. There were at least 4 California – DC roundtrips, California – Florida, California – Alabama, and more. Yet it never occurred to me to sign up for programs or credit miles to an account. My American miles had already expired — I hadn’t played around with miles and points for five years and didn’t again I started working. (Flying back from Alabama to California in 1996 I remember one person on the team signing up at the airport for AAdvantage but I didn’t stop to think much more about it.)

I Started Paying Attention Once I Graduated College

I’m not sure what prompted me to join a frequent flyer program back in 1996. I think that’s when I joined the United and US Airways program. I was certainly flying for work, and suddenly I was aware of the program marketing. I used some of my family’s British Airways miles to fly home to California for Thanksgiving on American, and that certainly underscored the value of miles and points for me.

I remember calling up United on the phone after each trip to hear my mileage balance, and see if flights had posted yet. I loved to hear that number grow from the automated Mileage Plus system. Back when I had 60,000 and then 90,000 miles in the account that seemed like a lot (of course 90,000 was enough for a business class roundtrip to Australia back then, with much better availability than we see today).

At the time I also stumbled onto a book one day browsing the shelves in a Barnes & Noble that set me off on a passionate journey with the airlines: Thomas Petzinger’s Hard Landing: The Epic Contest For Power And Profits That Plunged The Airlines Into Chaos, a great book on the business history of the US airline industry from inception through the mid-1990s (still probably the best book on the industry I’ve ever read).

My first full year out of school was 1997 and I earned elite status on United. I quickly figured out that even as a first-tier Premier member I could reliably upgrade if I avoided first flight Monday morning and Thursday and Friday evenings. I went for the big planes flying domestically — 747s and 777s back then! — and would almost always clear. I cared enough about the upgrade that I’d even try to stick myself on San Francisco trips flying 777s through Denver at noon on a Wednesday.

Back then I loved the United Connection disk-based reservations software. I still think that was a more powerful tool than what the bulk of booking websites offer today.

Hitting Premier status made me eligible to participate in United’s iDine program (that required elite status back then!). I remember getting my first bonus offer, miles for eating at four participating restaurants in a limited timeframe. I remember realizing that there was no minimum spend requirement listed at those restaurants, so I could go in and just buy a soda. That’s when I learned the value of reading through fine print.

United didn’t offer unlimited complimentary upgrades then. Upgrade certificates were paper, and checking in at United Express stations those paper upgrade certificates were rarely collected, so they stretched pretty far. You could buy more at a discount on eBay.

Confirmed domestic upgrades were 10,000 miles with no cash co-pay. United used to inadvertently post class of service mileage bonuses on those. So you’d be earning back most of the miles you spent on a cross country trip. You could also buy confirmed upgrade certificates on eBay which amounted to buying back miles somewhere between one and two cents apiece (although if you used the certificates checking in at a United Express station…).

I wouldn’t buy or sell upgrade certificates now. Back then I just didn’t know any better. Hopefully having purchased upgrade certificates on eBay 21 years ago doesn’t come back to haunt me. The MileagePlus (then ‘Mileage Plus’) terms and conditions don’t include a statute of limitations.

I get asked all the time now, as a result of my award booking service, whether I can help someone buy the miles they need for a trip or if I’d recommend a broker. I won’t get involved in those discussions at all. I just don’t think it’s worth the risk though I’m torn on the appropriateness of the restrictions themselves (value propositions are predicated on a certain amount of breakage which miles sales reduce, but I also do think consumers have a greater moral claim to ownership of their miles than programs generally allow).

I Made Plenty of Mistakes Along the Way

I started getting excited about credit card signup bonuses back in 1997. I remember when a new bonus came out for a Lufthansa card around 2001 and I signed up, not even paying attention to Miles & More’s expiration rules. I earned the bonus, but let those points expire too. So my 1991-earned American AAdvantage miles weren’t the only ones to expire.

Flying on a business class award to Australia in 2000 I visited a club lounge for the first time. I didn’t even realize I had access until I was directed to the United Red Carpet Club in Sydney on the way back. Then I snuck into the Red Carpet Club in Los Angeles before my connecting flight home, not realizing that my arriving boarding pass would have granted me access.

Incidentally it never even occurred to me to redeem miles for first class on that trip, even though I had the points and the increment wasn’t especially great (United charged 90,000 roundtrip for business, 120,000 for first). I never flew international first class until 2005 — 145,000 American AAdvantage miles apiece for Los Angeles – Tahiti (Air Tahiti Nui) // Tahiti – Auckland (Air Tahiti Nui) – Sydney (Qantas) // Melbourne – Los Angeles (Qantas).

And I almost screwed up that booking — I originally had Sydney – Los Angeles on hold, but American called me back to flag that I had held first class award space on an embargoed flight (not all Qantas flights were eligible for AAdvantage redemption then). Fortunately, booking 9 months out, there was Melbourne space home to the States a day later.

It wasn’t until 2002 that I first secured lounge access for real — by status matching to Mexicana Frecuenta Gold, back when the now-defunct airline was a Star Alliance member (they later left for oneworld). My Mexicana card got me into United clubs and I thought that was pretty cool. I took steps to make sure I always had access to lounges after that.

While I like to think I travel pretty well — gliding through the airport effortlessly, handling irregular operations with aplomb — my leisure travel is changing markedly now that I’m a dad. It takes longer to get out of the house (no more 75 minutes front door-to-gate), I wind up checking a bag, and need to be prepared for a bottle and diaper change prior to boarding. That makes me both appreciate my business travel more (traveling like I’m used to) and spending more time at home.

However I’ve made my share of mistakes, by far the biggest was when I showed up at the Sydney airport in the afternoon for a morning flight on Virgin Australia. I showed for the flight time when I originally booked the ticket, not for when it was rescheduled to, even though I had booked a hundred redemptions for people on Virgin Australia’s flight 1 to Los Angeles and knew what time it departed.

I’ve also showed up at the wrong hotel and also made a booking in Bangkok for the wrong month.

I’m Still Far From Perfect

I”m not a maximizing machine. Sometimes I will trade value for comfort and convenience, or give up miles for time saving. I probably place too much value on my time and effort.

But goodness knows I’m having fun!