One year is nothing. From experience I'd say that being poor is not hard for a year. It's the 3rd, 4th, 7th year, ... when your clothes all have holes that you've no energy to repair, your home starts to fall in to disrepair, you've been wearing leaky shoes for over a year, there appears to be no hope of ending your situation ...
He also had the privilege of a good education and good upbringing. You are making way too many assumptions to think that all it takes is wisdom and good decisions. What we can think and do is strongly shaped by our environment, and getting yourself out of poverty is harder than you think.