I have always found the YC application strange in that sense. So much emphasis is given to the question of the "most impressive achievement", but in order to convey any achievement with context, one needs to be quite verbose with their replies. Given that an application only has few seconds to impress, conveying anything is a challenge. Has YC given much thought to an essay type application?
I am proud of where I am today. I grew up in Mumbai, India (not quite a village). We weren't rich. I still have scars on my right foot from an abscess caused from a piece of glass that had pierced my foot while playing soccer bare feet on concrete. We couldn't afford shoes. Luckily my father's business started picking up around the time I entered engineering school. The plan was for me to graduate with a bachelor's in structural engineering and then we could work together to grow the business further. At 20, I earned my bachelor's in structural engineering. Unfortunately my father had died in an accident at work when I was in my penultimate year of engineering. I managed to get enough resources together to be able to attend grad school in the US. I met my wife there. BTW, she has an amazing story too. We now have a startup (https://magtag.me) that received angel investment recently. We feel like outsiders in the tech scene but our spirits are high and when we look back at our lives we feel nothing but pride.
My life is an ongoing achievement. Would you have time to hear me out?