Recently, I was made to look from afar on what I've accomplished at $WORK and even my inner critic had to agree that it's been a real success story. Paradoxically, this really killed my drive for a while. "I don't have to prove myself, to the company or myself. Colleagues and management are glad to have me around." Ironically (and thankfully) this resting on my laurels of course brought the critic right back.
So while I do like feeling 100% confident in myself and my skills, a healthy (!) dose of self-doubt is also necessary for me to stay humble and keep pushing myself. And this is true outside of work just the same.
Naturally, this need not apply to anyone else. But as positive as "being happy with yourself/your work/your lifestyle" sounds, it also risks removing the gradient toward improving your behavior/skills/situation. Or, put another way (in the spirit of TSAONGAF): You will always have problems, but maybe wrestling with your inner critic is a good problem to have.