biggest insecurity by age

We all know this forum is full of college students who feel the need to pose deep questions such as "what is the average net worth of MDs", so I thought I would spice it up this time and bring a fresh perspective. Hopefully those of greater wisdom can chime in and feel in the gaps.

Biggest insecurity for men:

Pre-college: will I get into an ivy league

college: will I land an internship at GS

intern: will I secure a return offer at GS

analyst years: will I land an associate role at APO

associate years: will I get into HBS

age 30: ?

age 40: ?

age 50: ?

age 60: why is that guy's yacht bigger than mine / why does that guy have a building named after him

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