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.
I'm the one who asked the question on Quora and I appreciate your response.
This, coupled with another answer that pointed out I've faced a lot of jealousy since my youth (a fact I wasn't aware of consciously but the jealousy did make me feel guilt) puts things into perspective.
I've gone from broke to, what is for me, a decent amount of money and while I can't stomach "blowing away" all my money, I want to buy (for instance) a designer handbag (I'm a girl) that's expensive but a fraction of my income. I hate people who make me feel like I should give it all to charity and not "brag" with an expensive bag. It's my money, I worked hard, I need to reward myself to keep going at this pace.
Accepting that "deserve's got nothing to do with it" makes life a lot easier, because it means other people don't necessarily deserve handouts from me either (excluding charity). Yes, I've already gone down the classic road of lending money to "friends" and relatives and never hearing back from them (it was a small amount to me and I can't be bothered to follow up, an easy cull).
Accepting that "deserve's got nothing to do with it" also makes it easier for me to shift focus away from the money. It's just another part of who I am. The major part of who I am is what I do each day - eat healthy, write like a demon, be good to those who I love.
This is why I asked you to answer - I'd rather hear from someone who's talked about the chemistry of success changing who a person is, than from someone who insists that you *must* stay the same person through it all and just appreciate it all. After all, it's a very "oh poor me" question, but I want to see more success with my writing (for selfish reasons) and I don't want anything (like guilt, which leads to self-sabotage) weighing me down.
Thanks again for the answer - would you mind if I copied out a bit on Quora and linked to your blog?
This is why I like a focus on excellence and discipline and kaizen for my life-- it is true that deserves got nothing to do with it, and furthermore attempting to tweak my actions for a particular outcome (monetary success, forex) can have an negative cascade effect (overwork, burnout, loss of focus in other areas that are important to me, and most of all, associating mostly with people who value monetary success over everything else.)
At the most, you can put yourself in a position to be able to take advantage of circumstances breaking your way (in the "the harder I work the luckier I get" sort of way.) But the corollary is that you have to be mindful of the fundamental attribution error. If you didn't succeed because of your innate merit, it follows that people who *don't* succeed don't necessarily have anything wrong with them. And if you can keep this in mind in business, you can find a lot of diamonds in the rough to work with, which I've always found to be an amazing investment in time and confidence.
Another desert hack: when you feel that you do not deserve something, interpret it as a sign that the universe is telling you that you need more experience in this area. So the things you don't deserve actually become beacons of interest.
Great stuff, Sebastian.
As Tim Ferris said in his new book, "some people become successful despite how they train and what they do."
Yep, most of success is luck (random causalities).Michael lewis said in this speech.  I'd like to point out that meritocracy is dangerous concept to hang onto.
"It’s a rigged system, rigged for the elites by the elites. Not maliciously. It’s just that they know not what they do. The system has been designed to make them feel good about themselves. As long as it looks like a meritocracy, they don’t feel bad about the inequality of opportunity. As long as there are a few token kids of extraordinary intelligence pulled out of the ghetto and given a free ride to Yale, they can suspend their disbelief about how the system they designed, the system they support keeps the masses from Liberty, Prosperity, and Dignity. They aren’t bad, they’re just ignorant, perhaps willfully so." 
This is really great stuff. It's important to get this "deserve's got nothin' to do with it" out of the way so we can focus on the craft of our lives, both personal and professional. Hopefully we do enough of the right things and as you say, catch the right breaks at the right time. A lot of people don't like to admit that a lot of things out of their control contributed to their success. They feel it diminishes their accomplishments. Not true. Regardless, great post and one of my favorite movies also.
Made my first comment on your blog recently and as promised, i'm here to make direct contact via email, officially deleting my name from the list of 900 :)
I'm blown away by the depth of the posts you make in response to emails from other folks for advice, so i'm gonna try my luck seeking some insights from you about my situation.
I just graduated from university about one and a half years ago.
So fast forward to today. Till now, i still only manage a low 4-figures monthly income from the internet business.
Okay, I've almost got all my email inboxes almost empty now.
I get a ton of mail. I hired an assistant and automated some of it, and I still get a ton of mail. More than I can answer normally.
I'm gradually building more systems, both technology, decisionmaking, and people to process all of this, because I have opportunities worth a lot of cash, a lot of cool stuff, and a lot of ability to connect with interesting people sitting in my inbox. At any given time, there's probably 3-4 very interesting things buried in the dozens of mails I get.
And I also get a kick out of helping people. I like getting and answering questions when I can.
But then I realized, one particular type of questioning makes me cringe, and I dont want to write back to people that write like that.