I showed up for the wrong flight, booked a hotel for the wrong month, and even drove to the wrong hotel out of pure habit—so here are five travel mistakes I’ve made while on auto-pilot (and why they still worked out). Along the way: the Sydney–L.A. departure I missed after a schedule change, the time I “snuck” into a United Club despite having access, the Novotel booking that was off by a month, the wrong Hyatt in Miami, and the AAdvantage miles I let expire.
I hate tipping because of the frictions. You don’t know what you’re supposed to tip, it’s ambiguous. You’re supposed to have cash? It’s so much better when employees are compensated by their employers and listed prices are the amounts you actually pay.
If tipping is supposed to ensure better service, why is it such a bad customer experience?
A share in my social feed reminded me of this incredible story that links Chicago O’Hare and Al Capone. It’s really two stories, but stay with me until the end.
One of baseball’s greatest hitters of all time was Wee Willie Keeler, who introduced the ‘hit and run’ play to the game when he was a member of the Baltimore Orioles. It was his 44-game hitting streak that Joe DiMaggio broke. It was his record of 8 consecutive seasons with 200 hits or more than Ichiro Suzuki broke.
And his batting advice is exactly how you maximize your chances of an upgrade for both airlines and hotels.
A single scene from the forgotten 1984 film Over the Brooklyn Bridge shaped how I think about negotiation, arbitrage, and frequent flyer miles. It’s a reminder that small efforts, when the stakes are right, can yield the biggest rewards — and that sometimes, the squeeze really is worth the juice.
A man was arrested at Orlando International after mentioning a “pipe bomb” at a TSA checkpoint—then claimed he was talking about a toy for his kids. Plus: a fresh Bilt 2.0 rumor says one card could let you choose 3x on dining or groceries (and switch the category each year), along with a $250 Capital One checking bonus, REAL ID skepticism, and Biscoff’s global push.
Southwest is going to add first class, and it’s basically unavoidable once the airline is selling basic economy and bag fees like everyone else. The problem is they aren’t built to deliver a true premium product—no seatback screens, limited power, and a cabin and galley setup that would need real investment for hot service—but without a top rung, their new fare strategy has nothing meaningful to upsell.
A viral video from Kansas City International shows a Southwest gate confrontation escalating fast—until other passengers step in to separate people and escort the man away from the counter – weirdly dependent on bystanders instead of security.
A cascading delay into Los Angeles was about to keep travelers from reaching the funeral of the Sydney rabbi killed in the Bondi Beach attacks. United wouldn’t hold its flight—but American Airlines did something airlines almost never do: it moved gates to eliminate the terminal scramble, held its own Sydney departure, and then comped a new ticket entirely. What followed was a behind-the-scenes relay from cockpit to operations to the gate that turned an impossible connection into a just-in-time arrival for the funeral.
One creative flight attendant – on what looks like Spirit Airlines – found a way to make passengers help out cleaning the cabin, as captured in a viral video. This flight attendant made an announcement, leading passengers in a stretching exercise.
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 InsideFlyer.com, 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 »
