Maximising outcomes by exploiting knowledge (and how things can still go wrong)

Sunrise on approach to Sydney
Sunrise on approach to Sydney

November 2015 was when I went on my third trip to the US.  This trips have presented an interesting experience in how one can learn things and then leverage that knowledge.  On my first trip, I was a complete novice.  I’d never planned a trip like this myself within Australia, never mind the complications of going overseas.  By exercising a lot of caution and care, I was able to minimise the chances of things going wrong.

Following that trip, I began a period of rapid education about travel and flights and all that stuff.  I quickly found out that the seats I had booked on the first trip were pretty bad (thanks Seatguru).  The second trip involved going on a slightly higher level of fare to mitigate some of the unpleasantness of sitting in economy for 14 hours, as well as just the experience that I might not get again.  All of the planning the first and second time involved a lot of manual work in Google Calendar, inputting place holder appointments for flights and hotel stays and other engagements, trying to keep a handle on the multiple time zones involved.

The third trip was the new apex in planning.  I managed to get all my air fares at very good prices, structured them for maximum benefit to my chosen frequent flyer account.  I also decided to put in for a points upgrade, given that doing so was one of the most effective ways to use the points and I now had a reasonable good status with the airline so my chances were good.  This time I also decided to use TripIt, which made the calendar population much easier this time around and essentially eliminated the need for paper copies of things (I still had them anyway).

But even with that level of things, some things still went wrong.  The hotel I stayed at in LA was still under renovation, this time it was the small convenience store I would visit for light snacks and coffee.  Ongoing sleep problems also came into play, as well as a few other things, some of which were out of my control.  Those will go into the lessons learned pile for trip #4.

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