On shoes and bags

I like to pack early for trips. A week before my / our departure, I'd usually have the bag that I am planning to use out and waiting for stuff and as I go about my day to day activities, I'd remember or think of something that I might need and I'd just drop that inside my bag. This is my way of making sure that I don't have to go without something that I need.

I mentioned in a previous post that I will be flying to Massachusetts this weekend to attend a week-long training at our headquarters. I'll also be staying on for another weekend for a meeting that I have to attend on Monday, this is the same client as the one which was cancelled due to a snowstorm weeks ago and I flew from airport-to-airport.

So now, am looking at my bags and can't decide whether I want to bring the small (hand carry size) roller bag or the medium one (which I'll have to check in) for my clothes. Hopefully, my stuff would fit in the smaller bag so I won't have to check anything in, I do hate waiting at the baggage terminal - and what I hate the most is when the airlines leave or lose your bag. Ugh!

I am also trying to decide which laptop bag to use, arte ba ? I have one which is small and compact (but heavy due to the padding) and a slightly thicker bag which is a roller bag. I find the roller laptop bag more convenient because I just have to pull it along and leave it on the floor whenever I stop and talk to other people. No aching shoulders. As for the smaller laptop bag, it has this sleeve at the back which you can slide down stroller handles so this makes travelling easier when you have both bags.

The thing is, if I'm bringing a roller bag for my clothes and another roller bag for my laptop, am not so sure if I can handle pulling 2 bags along - that would leave me with no free hands.

Me thinks I am over-analyzing this but it's really getting hard that I always have to go through this each time I leave - doesn't matter how long I'll be gone for or where I'm going, but I always have to go through this agonizing (heehee, drama) choice each and every time.

.. and don't get me started on what purse I want to bring... or shoes! I'm far from being a fashionista but obviously, I need to have something that matches. hay.