I am a bit frustrated at my self esteem. It doesn't make sense. I am always selling myself low.

Its stupid. There are guys out there who are homeless and feel totally comfortable in knowing that a girl who looks like a 9 is still right for them.

But I am not like this and it frustrates me because even with the following, when a 7 girl looks at me I look down: -enough cash to buy a house and a decent income -fit body, little fat, surfing every day -4 women around me into me, 2 climbing into my bed, others as female friends who like me

I'm thinking, what does it take for me to get the self esteem required such that the level that feels like my destiny matches what I feel about myself?

I feel I belong with a 8 girl. Not the 5-7's I've been dating.

What questions do you ask yourself to get the self esteem and self reflect, to look into oneself?

If I was to do it the hard way I project it would have to be millionaire, ability to surf double overhead waves or triathlon and 5 women interested before I can not look down when an 8 looks at me. But this is only a projection. I could still be hard on myself due to ego... So better to address it now.