I think part of the problem with realistically viewing one's life through this prism is the impossibility of determining what percentage of one's success is due to luck.
In a sense, literally everyone who is alive today is lucky. They are the product of an unbroken line of genetic material passed down for millions of years. Can you imagine? Not one of their thousands and thousands of ancestors managed to be killed before procreating!
In another sense, everyone alive today is lucky they weren't stillborn. Lucky they weren't claimed by SIDS or whooping cough, or a cold, or any of the various childhood afflictions we've eradicated. Everyone who wakes up tomorrow is lucky they didn't get cleaned out by a bus crossing the street, or sideswiped by a drunk driver on their way home.
Almost all of the "rich" people in the U.S. did not start out rich. Unquestionably, luck played a role. But how much? Who's to say that, if Michael Lewis skipped that fateful dinner, he wouldn't have gone to a frat party, met a future ballplayer, and then gone on to break the MLB steroid scandal. Or sat next to a White House intern and broken the Clinton sex scandal? or, or or. If any one of these alternate scenarios happened, he would still claim to be "lucky" to be in the right place at the right time. And, in a sense, he'd be right. But that doesn't necessarily mean he was successful because he was luckier than millions of other people around the world.
Obviously someone born today in the U.S. is much "luckier" than someone born in Somalia. Someone born into an upper-class family in Germany is "luckier" than someone born into a nomadic tribe in Algeria. Does that make the "luckier" person's success more attributable to luck? (And, as a corollary, the "less lucky" person's success less attributable to luck?) Maybe, but to what extent?
More important, in my view, is the reverse side of that luck equation: if you assume that input A leads deterministically to outcome B, then if you didn't get outcome B, obviously you didn't put in input A. Replace "A" with "hard work" and B with "economic success" and you have a nice justification for killing the social safety net, for example: obviously people who aren't successful must not be working hard enough.
So accepting that luck plays a role in success doesn't just affect your view of someone's success, it affects your view of other people's potential lack of success, which is an even more important thing to have if you want to have empathy for your fellow human beings.
Unfortunately, cognitive dissonance being what it is, a desire to attribute your own personal success to hard work rather than to luck makes it harder to attribute other people's failures to bad luck, and inclines you to assume that they must "deserve" their situation in life.
So I think it's less important to play the "what if" game there with specific situations, and more important to realize that people who haven't been successful might have been unlucky (or less lucky), rather than to try to decide whether someone successful was lucky or not.
This reminds me of a passage from Richard Dawkins' "Unweaving the Rainbow."
"We are going to die, and that makes us the lucky ones. Most people are never going to die because they are never going to be born. The potential people who could have been here in my place but who will in fact never see the light of day outnumber the sand grains of Arabia. Certainly those unborn ghosts include greater poets than Keats, scientists greater than Newton. We know this because the set of possible people allowed by our DNA so massively exceeds the set of actual people. In the teeth of these stupefying odds it is you and I, in our ordinariness, that are here."
I too thought of that passage but also this from Watchmen:
"There are thermodynamic miracles, events with odds against so astronomical they're effectively impossible, like oxygen spontaneously becoming gold; I long to observe such a thing. And yet, in each human coupling, a thousand million sperm vie for a single egg. Multiply those odds by countless generations, against the odds of your ancestors being alive; meeting; siring this precise son; that exact daughter, until your mother loves a man she has every reason to hate, and of that union, of the thousand million children competing for fertilization, it was you, only you, that emerged. To distill so specific a form from that chaos of improbability, like turning air to gold, that is the crowning unlikelihood, the thermodynamic miracle. The world is so full of people, so crowded with these miracles that they become commonplace and we forget. I forget. We gaze continually at the world and it grows dull in our perceptions. Yet seen from another's vantage point, as if new, it may still take our breath away. Come, dry your eyes, for you are life, rarer than a quark and unpredictable beyond the dreams of Heisenberg, the clay in which the forces that shape all things leave their fingerprints most clearly."
And if you recursively click the first link in Wikipedia articles, you end up at philosophy :)
My point is that if you dedicate a lot of time thinking about any particular aspect of life, you end up back at the "Getting to Philosophy" problem. Your luck comes in shades of grey. At some point, the line between black and white is drawn rather arbitrarily.
Would I consider myself "lucky" to be born in the US? To be born at all? Sure, why not. It's at least a statistical significance. But that stroke of luck was just the basis from which I built my relative level of success. The same is true for any starting point. The more relevant question is, does it really matter?
I wouldn't say that contemplating the deeper meaning of one's own "luck" is a waste of time, but obsessing over it is foolish. While you're busy contemplating how lucky you are, the other person is busy positioning themselves to succeed.
I think it really does matter, in at least two ways. As a person, and as a citizen.
As a person, I find it useful to consider how I've been lucky in that a) I'm better able to take advantage of the luck I've had, and b) it makes me more careful about downside risk. It also helps keep me from a certain fat-headed overconfidence. As the line goes, "Some people are born on third base and go through life thinking they hit a triple." I think that stunts people's growth.
As a citizen it's especially important for me in figuring out how to vote and what to advocate. I'm a big believer in the veil-of-ignorance approach: [1] In helping design a society, I should do it so that I would think it fair no matter which role I played. You can look at that as a way to subtract luck from the equation.
But no one would ever literally contemplate the single fact of their personal luck long enough to degrade their professional potential. It is realistic only that one might spend a few days a year or minutes a day at it. And occasional periods of self-awareness or mediation are almost certainly helpful in achieving life's goals. Instead, I take as Lewis's message that the successful should be and behave humbly. We should help those who live in less comfort or happiness.
In a sense, literally everyone who is alive today is lucky. They are the product of an unbroken line of genetic material passed down for millions of years. Can you imagine? Not one of their thousands and thousands of ancestors managed to be killed before procreating!
In another sense, everyone alive today is lucky they weren't stillborn. Lucky they weren't claimed by SIDS or whooping cough, or a cold, or any of the various childhood afflictions we've eradicated. Everyone who wakes up tomorrow is lucky they didn't get cleaned out by a bus crossing the street, or sideswiped by a drunk driver on their way home.
Almost all of the "rich" people in the U.S. did not start out rich. Unquestionably, luck played a role. But how much? Who's to say that, if Michael Lewis skipped that fateful dinner, he wouldn't have gone to a frat party, met a future ballplayer, and then gone on to break the MLB steroid scandal. Or sat next to a White House intern and broken the Clinton sex scandal? or, or or. If any one of these alternate scenarios happened, he would still claim to be "lucky" to be in the right place at the right time. And, in a sense, he'd be right. But that doesn't necessarily mean he was successful because he was luckier than millions of other people around the world.
Obviously someone born today in the U.S. is much "luckier" than someone born in Somalia. Someone born into an upper-class family in Germany is "luckier" than someone born into a nomadic tribe in Algeria. Does that make the "luckier" person's success more attributable to luck? (And, as a corollary, the "less lucky" person's success less attributable to luck?) Maybe, but to what extent?