Shorter Derek Sivers (at least every Derek Siders post that ever makes it to HN): "Hey, everyone, I'm rich and can do whatever I like. Isn't it great being rich? It's so much better than not being rich. Why doesn't everyone do it?". (Only with more boldface.)
(I took a look at his blog, including some posts that I didn't see on HN. Perhaps it's only 1/2 or 1/3 of his posts that have that form. But it does seem to be those that get onto HN.)
There is a saying: if you achieve your dreams during your lifetime, you aren't dreaming big enough.
Sivers has achieved a lot. But maybe he just needs to dream a bit bigger for himself?
Everyone should have a Polaris that guides them. An unmovable object / idea that helps in making life decisions. Because an aimless life won't be satisfying.
Heh. There's literally not enough money on the entire planet for most of my projects.
From the description, he's stuck in a rut. Instead of starting a yet another company, how about using the companies you have to fund something worthwhile.
There's a balance to everything. I don't think your issue, though, is having too much freedom. I think it likely has a lot more to do with not knowing what's right for you. If the right choice for you is to travel, you have the freedom to do it; if the right choice for you is to settle down, you have the freedom to do that too.
Freedom of choice without knowing the right path to choose can feel awfully non-free, though.
There is always something new to be learnt. New books to read, new knowledge to obtain, new culture to imbibe, new things to say, new experiences to be had.
Wait a minute, he answers it himself:
I'm definitely happy and complete, so there's no sense of longing or lacking. Just a constant pursuit of learning and experiencing all I can before I die.
Read The Sovereign Individual published 1997. Don't like your current location? Pick up your capital and move. (In the book, ultimately big government loses as the rich people move away and there's nobody left to rob.)
A dozen years later we've got a prime example. Yep, being rich is definitely better than not being rich.
(I took a look at his blog, including some posts that I didn't see on HN. Perhaps it's only 1/2 or 1/3 of his posts that have that form. But it does seem to be those that get onto HN.)