There are two realities that those that deploy the bootstrap trope seem to ignore:

1) Demographic Reality:

The world contains about twice as many people as it did when Baby Boomers were in their 20s, that equates to a job market that is at least four times as hard to succeed in (more, if you take into account the number of job opportunities that have been lost to automation).

2) Physical Reality:

Boot-strapping was coined as a joke (much like "trickle-down economics" -- am I detecting a theme here?). Boot-strapping is a synonym for levitating. "Boot-strapping" as a phrase sounds John Wayne-esque, levitation, by comparison is manifestly impossible, which is why no-one suggests that you do that.