Personally the problem I have with the whole "pull yourself up by your bootstraps" nonsense is that it ignores the fact that the way one is raised has a massive influence over how prepared you are to be successful in life. It is easy for me to say "well that person should know better; obviously it is stupid to carry high-interest consumer debt and live paycheck to paycheck". However, I can say that from the comfortable position of having grown up with responsible parents with stable careers who talked to me about money habits. I also have the education to understand new concepts, the training to seek them out, and the interest and confidence to learn new things. I have a stable job that allows me to buy things like computers and internet connection that facilitate my learning process.
Put another way, there is a huge disadvantage to those who don't know, and then don't know that they don't know. As a personal example, I always did relatively well by saving part of my income and living within my means. I started puttering around online seeking out personal finance blogs and articles simply because it was an interest of mine. It took over a year of bouncing from one column or blog to another before I stumbled upon MMM by happenstance. How lucky I did because it opened up this whole new world to me that I didn't know existed. Without that fortuitous online stumble I could easily be working until 55/65 instead of being done by 40. Someone from the outside could look at me from 4 years ago and say "duh, why doesn't she save more/invest better/educate herself about FIRE?". It is easy to judge from a position of knowledge and forget what it feels like to be in the dark and not even realize it.
My point with this ramble is that we are all human, we all have weaknesses, we all have limited time and resources. Overall I think we would all be better off if we set up our systems to nudge us into success instead of pointing fingers at people who don't make the "right" decisions, for whatever reason. What I mean by a system that sets people up for success is things along the line of providing reasonable opportunities for all for education, a social safety net for when things inevitably go wrong, nudges like auto-enroll retirement savings plans that you have to opt out of instead of opt in, using the vast power of marketing to nudge people to make healthy food choices, subsidizing healthier/more sustainable practices for living, commuting (i.e. zoning laws and urban planning), subsidizing healthy food instead of junk (how about an avocado or almond subsidy instead of a corn subsidy?), etc. etc. etc. Listening to some Freakonomics podcasts can give you ideas. Basically we can do a much better job setting up a system that primes people for success while still having plenty of freedom to choose otherwise, instead of our current default middle class lifestyle that is full of consumer traps you have to learn to avoid.
*side note: I read that the original meaning of the expression "pull yourself up by your bootstraps" was exactly as you would literally think it would be if you tried: something that is impossible to do and a logical absurdity to even attempt. I still think it retains some of that meaning, while the people who advocate for it are blind to the fact that you can't literally pull yourself up and that we all must rely on outside support structures to succeed, whether that is family, friends, education, a civil society with rule of law, access to information, or whatever.
