You make many excellent points, and I don’t think that your friend should be allowed to simply “jump the line.”

However…

While you could make (and have made) a strong argument for why the wealthy may have to thank luck more than any self-created virtue, I don’t believe that it would be in society’s best interest to conclude that this means that the most successful of us should not be more highly compensated than those who are less successful. Not for moral or ethical reasons, but for reasons of our joint self interest.

Systems that separate reward from creation of value (for whatever reason) tend to result in lower effort and productivity by most people, with severe negative impacts for society. Just look at the collapse of the old Soviet Union’s economy and you’ll see one example.

Does this mean that a CEO should earn 1000x the median income of employees in the business she runs? Probably not. How about 100x? Maybe, but then again maybe not. More than 10x? You’d be hard-pressed to argue against that. The crucial point is that there’s a slippery slope that you have to be careful of when you try to externally determine what should be the limiting multiplier.

Coming back to your friend, how about allowing him to compensate the other people in line with enough cash that they willingly let him to move ahead in line? If his time is worth so much more than theirs, he should be able to pay that extra value to the people whose turn in line he wants to jump.

If the person just ahead of him gets paid $15/hour, surely he’d be willing to let your friend move one spot ahead for $150. Then, if the person ahead of that spot earns $300/hour, the cost to move one more spot ahead may be $3000. Pretty soon, we’d get to see exactly how high a value your friend puts on his time.

Who knows, if there are 20 people ahead of him, and their average price point for letting him move ahead of them is $500, he might be willing to shell out the necessary $10,000 to save himself the 4 hours. If so, everyone comes out a winner.