Worked in different big tech for 7y, and took a sabbatical because I could, and so why not?
Well after a year of travelling and working on my own ideas and a bit of contract work, I entered a complete pit of depression. I mean contemplating ending it all to stop the pain. Instead big daddy Bezos was handing out tech jobs like candy so I took one begrudgingly just to have someone else to be accountable to, because I found it completely impossible to live with only my own expectations.
It helped. I'm halfway good again (or perhaps just a different, darker normal), with a different outlook on what and why I do things. But goodness.. I will never retire again. Not without kids to raise, or something/someone else to be accountable to.
Can you help me understand this perspective? Was there really nothing you wanted to do with your life that you had to resort to getting a corporate job to keep yourself sane? A guy a used to work with went through the same thing recently after his startup was acquired. I’m not sure how much he made, but I’m pretty sure he’s set for life. He stayed retired for about six months before getting bored and getting another job. It’s just completely baffling to me.
I want to sail the world. That is my one and only dream in this life. If I made enough money to retire, that’s what I would do. I would never dream of getting another job just to fill the time.
Granted, I’ve never been retired and probably won’t be for a very long time, so I don’t know for sure what it would feel like. But this perspective that retirement is boring and/or soul crushing just doesn’t compute with me. Maybe I’m missing something.
In my experience when you leave something you carry “doingness” inertia. If you carry that into a motivated and structured activity then you might have a great time, especially if you find others who want to do the same
thing.
If you dump your “doingness” into something that doesn’t feed back into your social connection or reputation, like playing video games alone in the middle of the day while everyone else is working, and expect Gandalf to drop in and send you on an epic quest, you’ll find yourself adrift at best.
From what I’ve seen, most people who find themselves lost do not have a “one and only dream in life.”
> expect Gandalf to drop in and send you on an epic quest, you’ll find yourself adrift at best
Oof, too true. It's a dangerous expectation that I had/have (and try to break) that purpose will present itself TO me. Probably because it did throughout my younger life, but only because I was inside of an institution which provided this (often with it's own motive).
(semi)retirement removed me from the institutions, and not being part of the regular rhythm of the work day can alienate you from your usual social network. Without a family demanding something of you, adrift is accurate.
Sure. I would offer two ideas which may resonate or not. They aren't provable facts, but experiences from my life and others'.
1. Part of your desire to sail the world is having it as a dream. It's the scarcity of being able to sail that gives it such high value. When you remove that scarcity with complete time and money freedom (and after some time, normalize yourself to it), the reality of sailing the world might change your perspective.
Now you have to acquire a boat, gain a shitload of knowledge, care for and repair it, invest significant effort to plan and prepare a trip, take significant risk being out on the ocean, be alone for months or recruit people to come with you, can you be alone with just them for months, is the opportunity cost of being away from family and friends for so long worth it... etc. It's no small feat.
Depending on how you are wired, your body might MUCH prefer to sit at home, eat tasty food, and submit to the youtube algorithm. Now that you have time and money freedom, you don't HAVE to do anything! I think your body knows it, and will optimize for risk reduction and energy conservation.
caveat: if there's something more here, like your late father taught you how to sail and you grew up on a boat, or your best friends are entering an international organized race, then for sure you will likely sail.
2. What happens after you sail the world? Do you sail it twice? Maybe you find it enough to just be at sea forever, but likely you come home to your apartment/house and .. do what exactly? The next thing on your list after "sail the world" perhaps, and repeat. If my first point doesn't terminate the loop for you, you can chase your next desire and next desire. Is that a life well lived?
Lots of people absolutely retire and live happy lives. But my sense is that they are much older, and so are still motivated by time scarcity, just in the fatal sense. Or they invest themselves deeply into something meaningful outside themselves like community, charity, teaching, caregiving.. or WORK! Then you'd be back to where you are, with some new experiences under your belt. Totally worth it. But I'd guess that almost no one puts their feet up and happily sips a mohito on the beach for 50 years.
Worked in different big tech for 7y, and took a sabbatical because I could, and so why not?
Well after a year of travelling and working on my own ideas and a bit of contract work, I entered a complete pit of depression. I mean contemplating ending it all to stop the pain. Instead big daddy Bezos was handing out tech jobs like candy so I took one begrudgingly just to have someone else to be accountable to, because I found it completely impossible to live with only my own expectations.
It helped. I'm halfway good again (or perhaps just a different, darker normal), with a different outlook on what and why I do things. But goodness.. I will never retire again. Not without kids to raise, or something/someone else to be accountable to.