Henry understood the meaning behind "being a loser" shortly after he graduated college.
There's a slight difference between knowing the literal definition something and understanding deeper what it means in reality. Henry, who had always lived within his slow-paced comfort zone used to think that the word 'Loser' could only be applied to those people — the jerks that could do nothing but annoys the people surrounding them. Criminals are also included, but not all criminals are bad, some of them could be justified even though it's a rare scenario to see. As long as someone has good personality, then it wouldn't be right to call them loser wherever they placed within society.
But that's hit opinion from years ago, when he was young and naïve. After living as a grown adult and became another piece of cog in society, he was finally proven wrong. Good personality is just a baseline for somebody— a must have trait and not something that would make you not a loser. Your worth in society basically consisted of your looks, talent, achievement, and capability. Everything else is just a supplement to make everyone looking at you with favor, nothing more than that. Someone who failed to prove themselves to have one of those things are the ones that could be called as loser.
The reason they are loser are because they are the lowest caste in society. Working low-paying jobs to survive, living paycheck to paycheck, and taking shelter in dilapidated housing, they are the bottom dwellers that can't move upwards since they lack what it takes to do so. They must be content rolling in the mud as they don't deserve to get more.
Henry, in his 25th year of living, has remained as a loser ever since. Working part time job in a fast-food restaurant could only give him pennies so he has to rely on his inheritance he got from his parent to survive.
In the end, his saving would someday be gone, and he must find a way to make more money to keep himself alive. Otherwise, he might end up on the street, living side-by-side with those lifeless drug addict that would be more fitting to be called zombies than human.
One of the most disgraceful non-crimes acts that someone could do is to not contribute to society, which basically means being jobless and not paying taxes. It will only take a single layoff and Henry would fall into being in the lowest caste of lawful society, so he must be careful.
That being said, perhaps you could be jobless as long as you have the money to sustain yourself. It's because you don't smooch out of other's pocket, so you can just live however you like. This is the only exception to the rule: having so much money you can just buy your way through everything.
But that kind of scenario is just a wishful thinking. The chance of that happening is almost zero if you are already born, since most wealth is inherited from your predecessor. In other words, the chance of it happening is so low it practically is impossible to happen. Deluding yourself into such hope of getting a sudden struck of unimaginable luck is a terrible source of motivation to keep living.
However, there might actually be a case where it happens.
An insane amount of luck, with a chance less than 0.1% to land, would eventually went to someone who the goddess herself chooses. An insurmountable wealth will descent to someone beloved by the goddess of luck, turning his life upside down in a single instance