I was asked to answer the question, "How Do I Overcome My Guilt About Success/Wealth?" on Quora. I wrote this up for there --
You know, my favorite quote from any movie is the end of Clint Eastwood's "Unforgiven."
Unforgiven is a sweeping human drama, which no clear good guy or bad guy. You have a variety of antagonists and anti-heroes, and no clear cut "good guys."
In it, due to the sweep of human emotions, at the end you wind up with a slightly overly brutal and sadistic sheriff who nonetheless has mostly good intentions... pitted against a former murderer and outlaw who wants to avenge the excessive and inappropriate killing of his best friend (who was a decent guy who got caught up in events outside his control).
Neither is the "good guy"; both are bad and hard men.
Eventually, one of the sides shoots the other fatally. The losing side, laying there bleeding and about to expire, says, "I don't deserve this. I just built a house."
The winning side?
"Deserve's got nothin' to do with it."
Each side could claim a moral high ground, but the final encounter had nothing to do with justice or cosmic fairness, and everything to do with vagaries of mundane events: a gun jams, someone is quicker on the trigger, a stay round goes this way or that way, and the outcome is decided.
It can be intensely liberating to realize that most of human life is like that.
Deserve -- and morality and justice in general -- has a lot less to do with success, winning, and losing than most people want and need to believe.
Most of success is causality, and as you get more successful, you realize that there's a hell of a lot of chance that's outside your control. Sure, you can minimize that by practicing hard, treating people well, constantly learning, looking to be very valuable, working hard, executing, focus, looking to understand the field you're in...
...but then, you can't help but noticing that some amazing people don't break through, and some lesser lights do, and you're sitting there pondering this.
So to answer your question, "How can I start to feel like I deserve my wealth and success?"
It's pretty easy. You remember that deserve's got nothing to do with it.
Or at least, less than you'd think. The emotion, customs, and feelings -- which are normal and quite common, by the way -- have not so much to do with why you broke through and became successful.
Really. You're wealthy because you did some of the right things, and some forces that could have broken this way or that way broke in your favor.
I dare say that you could even dissolve the question -- do you need to feel like you deserve your success to be happy and do what's meaningful to you?
It might be a strange and crazy question but really, think on it for a moment.
You're where you're at materially right now, not because of any morality, ritual, or custom. You took some actions (honing your writing craft, writing, editing, promoting) and you became successful through a mix of your own actions and forces outside your control breaking the right way for you.
Now, you want to be happy and effective going forwards.
Is, "Do I deserve this?" even a useful question for you to think and meditate on? Or can you keep your eye on the ball that matters to you. Questions like, "How do I keep improving my writing craft? How do I keep delighting my readers? How do I be the best spouse I can be? How do I treat people well? How do I keep learning and growing? What do I find meaningful in the world, and how do I do more of that?"
Your ethics, morality, and values are key to you. But there's 10,000 philosophical, moral, and ethical questions you could obsess over. I dare say there's a right answer to, "Do I deserve my success?' -- which is to stop thinking about it, realize that deserve's got nothing to do with it, and to move on to weightier questions that will guide your pen and footsteps and moving forwards.