Extreme Business Travel stories

Business Travel is the most fickle part of my job.  I travel enough that I’m in upper tiers on airlines, auto rentals, and hotels.  I’m also pretty good at it due to practice.  I do decent job of planning so that I can easily get 3 cities in a week if required.  I have had to change plans including re-routing at my layover airport to new destination, but the plans gave me ability to adapt including the fact I always carry a raincoat.  Sometimes, it just doesn’t seem to matter what I do. 

In the last month, I’ve planned and executed well and had terrible results, and of course the inverse where I planned and executed poorly yet had a wonderful result.  Interestingly, both were the same airline, Delta, and out of New York Airports – LaGuadia Airport (LGA) and JFK (JFK).

First, the not so good.  I planned to take a flight from LGA to Fort Myers (RSW).  I started in New Jersey, so got there extra early to avoid the traffic since the flight was at 7 p.m.  I was extra early since it was raining and there were major storms in the area.  I knew I was in trouble when the times started pushing back by hours.  Eventually it cancelled.  The alternative was to depart at 10 p.m. to Tampa (TPA), rent a car and drive about 2.5 hours to home.  I had 8, 9, and 10 a.m. calls I needed to be on in the morning with the 9 a.m. requiring me to review a document. Unfortunately, the TPA flight was delayed and didn’t take off until 2 a.m.  The result was I got into TPA around 4 a.m.  I took a hotel, took my calls from the hotel, and got home around 1 p.m.  I had done everything right, but I lost.

I had the inverse, too.  I had JFK to San Francisco flight 7 a.m.  The airline adjusted the take off to 6:58 a.m. which I somehow read as the flight was at 8 a.m. or at least that is what I had in my head.  I had a really nice mid-town NY hotel, but that night I didn’t sleep well and found myself watching clock.  At 6 a.m., airline app gave me an alarm telling me I had 20 minutes to boarding and I’m in my hotel room in my undershorts brushing my teeth.  GASP!


  • 6:00 Panic! 
  • 6:01 Don’t Panic per the Hitchhikers Guide to Galaxy (valuable even if fiction)
  • 6:01 Dress, stuff suitcase, etc.
  • 6:10 Ask for car via UBER (love that app).  The account is tied to your credit card, so no long goodbyes or failed credit card transactions at curb as with taxis
  • 6:12 UBER driver meets me on the curb with trunk open in front of hotel
  • 6:15 Looking up alternative flights for 2:00 pm PST meeting (none on my airline, so big $s if I miss the flight)
  • 6:30 Traffic is light and the driver is moving quick, but not insane. 
  • 6:46 Dropped off at the curb at JFK
  • 6:48 Go through TSA line asking for Pre-check and telling them “I screwed up, mis-timed my flight, and it was my fault”
  • 6:49 TSA agent closes her stand, walks me to front of the line, puts my bags in the front and puts me first in for the scanner
  • 6:52 Walk to JFK Gate 62 which is about 20 meters from security with my belt and shoes in hand
  • 6:54 Gate agent hands me an upgraded seat for the 5+ hour flight
  • 6:56 Butt in seat 44 minutes from mid-town on a weekday morning
  • 6:58 Sent a nice tweet to the TSA for their angel of an agent
  • 6:59 While shutting down I check the PDF bill for UBER (got to love it)

If you judged travel by these 2 sensational accounts, you’d argue planning doesn’t matter it is all luck.  What is missing is the boring part – the other 50 weeks where I made my flights with no real ups or downs, but got there on time according to plan.  Too often we define a topic based on the extremes and the sensational.

So besides being a good story, there is lesson.  Build your plans to give you enough structure to support your requirements, but enough flexibility to adapt to inevitable changes in your business.  Most of the time it will work to your advantage and sometimes no matter what, it fails due circumstances beyond your control.  All you can do is roll with it. Finally, sometimes you get help from an unlikely source – just be sure to send a thank you note / tweet / e-mail.  Even angels need encouragement.