I kind of see what you are saying, but for me 'settling' was the means of achieving happiness, that pleasant life you mention.

I had set high expectations of myself, far higher than I asked of anyone else; because you have to keep pushing for more, right? If you aren't pushing you are settling, and everyone keeps saying you can do more, have more, be more, want more...

But actually settling and saying 'I have enough', 'I dont want things I don't need', 'my needs are small' released me from the treadmill of false expectations.

Examine what you want, and ask yourself why you want it? You want to travel the world, why? Because you see others doing it and they look cool...?
You want a big house, why? Because it allows you to have a special status within your peers...?

Settle and have an easy life... :)