When I was younger I missed the boat on a very successful local startup. The people who graduated a few years before me and joined the company at the right time exited with multi-million dollar equity. The CEO’s equity was in the 9-figure range.
I remember being intensely jealous that I had just barely missed the boat on that life changing equity. Just a couple years difference and I would have been wealthy enough in my 20s to never have to work again. I fantasized about all the ways I would live my life.
Over the years, the only people from that lucky group who remained happy were those who continued on with their careers as if nothing had happened. The ones who used that opportunity to exit the workforce have been universally cursed: Divorces, unhappiness, and now seething anger at the world and society. There’s a Slack for former members of the startup that I’ve been in for years and it’s sad to see the swirling anger and unhappiness of those who left the workforce.
I never would have predicted it at the time. The way people fantasize about not having to work is often very different than reality.
I know it’s not literally everyone who has this experience, but after seeing it happen to so many people I know it’s also not a rare outcome.