First, a sale of $14M doesn't get you $14 - you'd get less than 10 - best case.
Second, your after inflation return in the current environment may be quite ugly - $300K or $400K a year will not feel rich in any east or west coast city.
The reason people with $300K household incomes in Boston/NYC/Silicon Valley don't feel rich is because out of that $300K, they're buying housing and saving for retirement/college/rainy day. Take that away, and $300K spendable is a fairly luxurious lifestyle.
If you don't feel rich at that point you need to get your head straight. Obviously there is always someone richer, but you are deep deep into the 1% of the richest country in the world and you need to be thinking about your greater life's purpose.
Live anywhere near Silicon Valley and tell me 300-400k/yr is rich. You'd be lucky to get a nicely located condo at that income level.
You need a minimum of 120k, just for your house. Pre tax you’re looking at a minimum viable salary of 300k.
How is this unfathomable?
The entire row of condos sold in less than a week.
If that situation feels "minimum viable" to someone, I don't think their primary problem is money-related.