Be aware that it took me several years to qualify as an instructor with over 200 jumps! It's not something you're likely to do on a gap year - that's why it took me 4 years to get there and did it after uni!
Also I travelled over 10 years ago so before all the 9/11 and all the stringent travelling laws and regulations making it much easier and more fun too - it might be less fun now - I don't know... You do need to plan it more now than you used to probably. So have a rough idea, but also be open to changing destination and direction. You can't be shy, you have to be rather self entrepreneurial in terms of selling yourself. You also have to be aware of people taking you for a ride. I have not scary stories to tell, but I got in a few dodgy situations (ended up behind bars twice, and in some drug lord/crime lord's property

not fun!) However, the plus sides I experienced I can't even list on one post the main ones being: women, sights, friends, once in a life time experiences. In fact I'm getting rather excited talking about it and thinking about it!!
Before I left I did some part time work for a small IT company, some bar work/door work which whilst living at home with the 'rents made for a decent bit of disposable income.
After uni I spent a lot of time in the States and in France throwing myself out of planes which was fun! Then got myself a proper job and continued travelling the world as part of it - so it was good fun! Until I had enough of the travel - after 7 years of living out of a suitcase it gets old.