There is a wonderful line in Negotiation by Brian Tracy.
The future belongs to the askers. The future belongs to those people who confidently and boldly ask for what they want, and ask again, and continue to ask.
This is incredibly true for a whole variety of reasons, the main one being that it opens up opportunities that weren’t there before.
However, you do need to ask, and it can be tough to strike the courage to do so, because of the innate fear of rejection that we all possess, and that is why it’s important to practice smaller asks first.
Ask for everything, hotel upgrades, discounts at restaurants, anything.
Ask “why not?”.
Get used to asking for small things, and before you know it you will have the courage to ask for big important things, and that’s when life begins to get really interesting.