Move to Europe, and you can take a month long vaction like everyone else.
I'm not quite old yet (everyone would say that, right? I'm 35), and I don't regret my younger self at all: during the past 12 years I worked cumulatively 9 years and had 3 years off inbetween jobs. I managed to save up some money, as well as travel and have time for myself.
Ever since I had kids, being forced to work for a living has been a massive weight on my life. Inherited wealth would be a great help.
Luckily, the fact that I don’t expect to inherit much of anything gets me out of the moral implications of wishing anyone’s death (which is actually the second biggest worry, at the back of my mind).
The problem with these kinds of hypotheticals is that had it been that way, you would not be the you that feels this way.
Aged as I am now, a windfall like an inheritance or a lottery win would probably be invested sensibly towards my retirement. But would a much younger me have blown it all on bitcoin speculation or something equally dumb that seemed like a good idea at the time?
There will always be choices that I would have made that my future self will deem wrong.
How do I deal with this? Is the key to happiness when older is to just lose all memories?
If you spend your youth having fun and enjoying your youth, then when you get to middle age you'll have wished you worked harder and saved more so you could be wealthy and comfortable.
If you work your butt off in your youth and have lots of money and successful career, you'll wish you spent more time relaxing and having fun in your youth.
The key is finding a good balance between working hard and playing hard. Your career won't suffer if you take a week long vacation. Your health will be fine if you sometimes volunteer to do a weekend shift. Do both and you can be successful and happy about how you spent your youth.