What is your understanding of "assertive" ?
Che Guevara ? Elon Musk ? ...
Duh, there are not only two-three humans on Earth to define positive traits... I don't like both of them btw...
For the definition of being assertive :
Assertiveness is the quality of being self-assured and confident without being aggressive. In the field of
psychology and
psychotherapy, it is a skill that can be learned and a mode of communication.
Dorland's Medical Dictionary defines assertiveness as:
a form of behavior characterized by a confident declaration or affirmation of a statement without need of proof; this affirms the person's rights or point of view without either aggressively threatening the rights of another (assuming a position of dominance) or submissively permitting another to ignore or deny one's rights or point of view.
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It is considered a critical life skill and recommended for children to develop. While not currently taught in schools, assertiveness is a communication skill that can be taught and the skills of assertive communication effectively learned.
Assertiveness is a method of critical thinking where an individual speaks up in defense of their views or in light of erroneous information. Assertive people are able to be outspoken and analyze information and point out areas of information lacking substance, details or evidence. Assertiveness supports creative thinking and effective communication.
The level of assertiveness demonstrated in any human community is a factor of social and cultural practices at the time of inquiry. For example, in 2019 there are global public discussions about controversial topics such as drug addiction, rape and sexual abuse of women and children, which were not openly discussed in 1940.
Within families, children are not always encouraged to develop assertiveness skills and must usually accept and obey rulings by their parents. Today, however, outspoken children can legally input to decisions about their lives from the age of sixteen.
en.wikipedia.org
Is there any natural reason why should someone be broke and suffer unnecessarily ? In essence it's really a socio-economic reason.
If someone didn't worked hard i.e. he/she is/was extremely lazy or stupid beyond redemption then he/she deserves that.