[Joeaksa]

If you are going overseas, especially some parts of Europe (Switzerland is the worst) they will weigh your carry-on bags, so be carefrul there.

Which class are you flying in? First or business class gives you more latitude than "flying steerage" where they follow the rules. Also if you are a frequent flier they will look the other way if you bring a heavy bag as a carry-on in some places.

I used to fly overseas all the time and carried a small cordura briefcase with reading materials and passport, then a tote bag with my laptop and other important stuff inside. All jewlery, money, paperwork, medicine and so on ALWAYS goes with me and is never checked below.