How I Prepare for Travel

I have a big adventure to Cuba this coming January, and a few shorter business trips before then. I'm preparing for them right now.

I embrace the "dry run" school of thought for packing. It's my belief that we cannot conceptualize everything we need (and just as importantly, don't need) without physically trying things out first.

My preliminary kit for Cuba includes:

That bag is packed now. I carry it back and forth to work everyday, and it will accompany me on two business trips between now and Cuba. 

During that time, I will determine if the backpack is too heavy, if there's gear that I'm not using, are their additional lenses I should add, and am I self-sufficient?

I could not answer those questions properly the night before the flight to Havana.

I need to know now.

And that's how I prepare for travel.