I consider myself an expert air traveler.  Since 2004, I’ve traveled around 35 weeks each year (of course this ended in 2020 and is only now beginning to resume), mostly by air.

I wasn’t born with this knowledge.  It’s something you only learn first-hand.  Here are my top five lessons (and how I learned them).

  1. Pick One Airline and Be Loyal to It.  Early in my career, I took whatever fare was cheapest.  It wasn’t until I selected one primary airline (Southwest), got the Southwest Visa card, and earned loyalty and travel benefits that I learned this.  Now, I get premier boarding, priority when making last-minute flight changes, and a ton of free drink coupons!
  2. Never Check Luggage.  In 2005, I flew from Dulles to Great Falls, Montana, connecting through Denver.  I checked my bags.  While in Denver, I learned my connection was cancelled and United (see Lesson #1) dumped me on a flight through Salt Lake City.  I arrived in Montana after midnight.  My luggage did not.  That meant the next day I led a workshop in my travel clothes.  I’ve never checked another bag since then.
  3. Fly Direct Whenever Possible.  Sometimes you can’t, but if you don’t, you’ll always risk a missed connection.  About 15 years ago, I flew from Sioux Falls, SD to Memphis, TN via Chicago O’Hare.  The SD flight was delayed.  Very delayed.  By the time I got into O’Hare, my flight was long gone.  I was able to book one out the next morning, but it was too late to get a hotel.  So, I spent the night on the floor, listening to a hell-loop recording of United Airline’s theme song, Gershwin’s Rhapsody in Blue. All. Night. Long.
  4. Always Take the First Available Flight Out.  You have about three good flying weather months per year in the USA:  October, November, and March.  After that, you worry about thunderstorms and snow.  The earlier your flight, the better chance you have of avoiding weather problems, but that won’t matter if your connection is in a bad weather location.  Yeah, it sucks to be at the airport at 6AM, but not nearly as bad as sleeping on the airport floor.
  5. Be Careful Where You Connect.  Finally, if you must do a connection, avoid the following airports if you can: Philly, Newark, JFK, LaGuardia, Reagan National, Charlotte, Orlando, Miami, Atlanta, Dallas, Houston, Denver, Minneapolis, O’Hare, LAX and Seattle.  Two reasons:  Weather and air traffic problems, and I’ve personally had issues here.  Leave early, fly direct, and connect in lighter markets!

Now, this wasn’t just a post of travel tips.  Each of the lessons above were learned through experience. I failed, and learned from that failure. If I read this in a book or blog post, I’d probably ignore it, but the School of Hard Travel Knocks was a much better teacher.

We all make mistakes.  Our only salvation is learning from them.  What hard lessons are you benefitting from today?  If not, you’re wasting them!