This couldn't be more spot on

I was born in another upper middle class family and somehow we've gone from building houses and buying cars to not even having $150 to repair our broken down generator... All in the space of about 10 years

I've vowed not to make the same mistakes my parents did, but am afraid my management skills are still quite limited

Am sorry about your portfolio man, must be rough but this too shall pass

You will surely bounce back