Beginner's luck

What's that? when you try something for the first time. You do it without any fail. People will tell you when you had it ;)
It is generally associated with the task which is complicated.
So how this may happen. My hypothesis is that when you attempt the first time any complicated task, you are ready for any failure and so you are at peace. No pressure! That will give you the flawless brain power which one does not have especially once we try it after training. After trying a few times, you are expected to do it without fail. That makes you worried somewhere leading to fails. Having said so, it's not universal law (for that matter just a hypothesis by me). Although, this may be the case for some  :) 

A dreamer, an achiever or a criminal??

Somesh is an accountant in a private firm. He is hard working but earns little money. Just enough for a lifestyle of a lower medium class. He had this desire to be rich someday in his life. He witnessed around him that the rich are respected and admired. He wished that for himself. 
He started stealing money from his boss's account smartly. He covered his steals on paper. He is too smart to be caught. I must mention his boss keeps the black money so the boss is not a 'saint'.
Somesh is very rich. It's been a while. He bought properties. He spends money on his family and extended family. He is known as a kind rich fellow with gentle behavior. With his open secret, society still loves and respects him. 
Tell me guys- Should Somesh feel proud of his achievements? Should people who are aware of his acts, should still respect him? Is it okay to be okay for him? or let the conscious make you feel, he is just an ordinary small thief with a white collar...