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Yes, those pack / don't pack decisions...
You never want to be having to make them as it's hard to think properly when you have been on the road for a while and the chances of making a shit decision are quite high. You do have to make some decisions and I try to save my brain power for the ones that I need to get right to stay in the race.
I'd forgotten that I packed on IndyPac at one point as I was sure I was out of time for my flight. Then I had a big curry and a long sleep in a hotel, and realised I didn't have anything else to do, or any other clothes to wear, so just started racing again as it saved having to make any other plans.
Yeah, I almost bailed on my second TransAm because I'd miscounted the days and booked the flight way to early (like, even if it went to plan this time, too early). Thankfully @DarrenFranks helped with flights so I could finish the ride properly.
Transiberica last year was similar - too many issues meant I was way behind schedule and then it gets to the point where you spend the rest of the race stressing about finishing in time versus just pulling the pin. For once, I pulled the pin and had a relatively comfortable return home with the time I had in hand.