My point with this story is that if you are making way above the median salary in NYC ($200k+ range at the time, this was 10 years ago) - the world is just different. You are making enough money to enjoy one of the top cities in the world. With the $125k-$140k salaries some software developers report making, they are barely getting to "enjoy" living in NYC. Finance has distorted the baseline of what it means to be successful in NYC. I mean, my school friends' coworkers were 2-3 yrs out of Harvard and talking about the travails of $80k car ownership like it was an Accord.
Software salaries outside of Fintech and top-tier companies like Google and Facebook and a handful of others in globally attractive cities are the equivalent of middle class in the burbs. You're doing OK but you're not going to be relatively 'really doing well'. In a city like NYC, there are more than enough free events to overwhelm anyone. However, in San Jose, what do you do? Hang out on the Palo Alto main drag?
Check out the size of the dogs being walked near Central Park. Where do these people live?!