The same can be said about real life...some people prefer to take something rather then work for it. I used to know someone whole stole what they can, because they can and it wasn't born out of necessity or desperation, they simply enjoyed stealing.
If my characters join the Thieves Guild, they do so for training. Same with The Companions or the College of Winterhold.
I see it as a "place for higher learning" with the skills they offer, like sneaking, lockpicking, 1-Handed, light armor, and such. My characters may do the quests in the Thieves Guild (once joined), or they may just use it as a base of operations and training. (I almost always do the quests, though )
The Thieves Guild, for me, is a stretch on my own morality, but I sacrifice that for gameplay. I enjoy being sneaky and defeating locks