I get where you are going with this, I really do, Ohai. It’s not incorrect.
The Original Poster is basically saying, “I don’t want to work like this forever.” But, he wants to maintain his high paid lifestyle. (I’m with him, I think we all are) I do not think that you need to work hard, the way many of us do, to make a lot of money. I also think that you do not have to have a job where you are constantly competing to keep your job in order to make a lot of money. Isn’t that why some people put in 100 plus hours a week, because if they don’t someone else will and snatch their job?
Yes, wouldn’t it be better just to cash out at some point and park your money in something that you are the boss of (can’t get fired) and work at your own pace? Not everyone can stay in the finance and investment industries forever. Most of us will quit it by the time we are in our 40’s. Wouldn’t it be nice to get that noose off your neck? To know that you had a decent income generating business on the side that could support you and potentially your children if they are not smart enough for a finance job or if they industry ceases to exist by the time they are adults.
It’s diversification of your income streams actually. So if we want to be purely theoretical, won’t that simple act of putting your capital in something unrelated to “finance” probably reduce the volatility and standard deviation of your personal return? I have a lot of friends that own apartments in cities like london and rent them out to other people. This gives them a source of income should they lose their own jobs.
Your success will largely depend on this skill that you are talking about in “spotting opportunities” or managing whatever business you buy. But at least you won’t be competing with 20 year old asian math geniuses. 20 year old asians. don’t own hotels……. yet.