Bootstraps are things that everyone has, but the only people who have ever used them are rich people. If poor people had used them, they wouldn’t be poor. Their bootstraps remain, unlaced, disheveled upon the floor. This is how we justify our system: it is merit-based. Those who attain power within it must have that power legitimately, and legitimacy is seen as being earned through hard work. The powerful, those who noticeably do not generally wear boots, obtained their power through the literally impossible task of pulling themselves up by their bootstraps.

He must have been poor
To deny the bootstrap theory is not to proselytize a Calvinist social doctrine where some are preordained with salvation through inherited grace while the rest are condemned to poverty and damnation. Social forces, however unjust, will never be immutable. If things can change, then it must be the people who change them. The capacity to change must then exist, and if not through bootstraps, then how?
Imagine two people in two separate hallways at the end of which lies a mysterious door. The first person opens their door, and a litter of adorable puppies is revealed! Behind the second person’s door is a literal crack den with someone offering them a pipe. Both doors offer a choice, it’s just that that choice depends entirely on which hallway the person happens to be in. The person being offered crack could say no, sure, but the person playing with the puppies didn’t even get the opportunity to smoke that delicious crack.

I know what I’D choose
There will certainly be things that influence that choice. Did the second person receive an accurate education regarding the nature of drugs? Did they witness drug use during their formative years? Did they suffer a previous trauma that they never learned to cope with? Is the first person allergic to dogs? There are always correlative factors that influence choice which explain statistical trends, but choice does exist to explain anomalies.
The thing is, we don’t choose our doors. A door may open, and behind it may lay overt racism. Behind another door may be an abusive partner. Behind another door may be a downsizing layoff. We can only choose our reactions to these doors, but our reactions will always open more doors towards which we must again react. A woman might open a door to sexual harassment at work, and how she reacts might open another door that reveals a misogynist work environment, and her following reaction might open a door to reveal hostility at having rocked the boat.
Privilege is living in a hallway with mostly benign doorways. Merit doesn’t enter into it at all. Don’t have to react to racism? Congratulations! Don’t have to react to sexism? Congratulations! Don’t have to react to growing up in poverty, undergoing abuse or neglect, being followed home by a cat-caller, learning your times tables in an underfunded educational system, walking down the street with an authoritarian police force, or making a shitty wage under precarious employment? Congratulations! Resilience is a thing, certainly, but if doorway after doorway is consistently negative, a negative anti-social status is far more likely to develop.

I’m sure it’s fine
Like I said earlier, we’re not Calvinists. Choice is an option, and our hallways are not preordained. They are evolved, shaped, and constructed through social history, economic factors, cultural attitudes, and policy decisions. Someone on the LGBT spectrum would not have to react to homophobia if homophobia in all its social, cultural, economic, and political incarnations wasn’t a thing! On an individual level, encouraging resilience is not the worst thing in the world because often in that precise moment there is nothing else really that an individual can do. Even if that is the case, being aware of the context of that person’s situation is going to massively improve your compassion and understanding, vastly improving their likelihood of listening. However, encouraging bootstraps in any other capacity completely ignores that we all live in different hallways, and that we, collectively, can actually improve what’s behind those doors through our evolving culture, our economic system, and our political decisions.
So let’s do that instead.
I like this metaphor. It reminds me of something called the empirical fallacy, which is why I’m distrustful of advice from people of very different backgrounds from me.
Unfortunately, people that come from very different background from mine are precisely the sort of people who think they should be micromanaging society. People like me have no illusions that we know what’s best for other people. (I went through a wounded Samaritan phase long ago, having been brainwashed by do-gooders. I am so over that now.)
I just concentrate on figuring out what’s best for me. If I give advice, it will rarely be specifics of what to do, but only hints on how to figure out for yourself what to do.