I would imagine in the future it would be silly to think that people did this merely to make a small profit, when they will then realize that they just went against everything they initially stood for in terms of getting away from government mandated currencies.
Because I am in it for the long term, I hope that when/if I one day spend my "eta" that I will do it directly. I fully expect that I will never 'sell' up to 50% of the Monero I acquire in these early stages. I actually like a modified form of Risto's plan, where every time the price goes up 10x you sell/trade 10% to increase the available supply and upgrade the quality of your life a little bit.
That might be for dollars, land, stock, etc.... Whatever is valuable at the time.
Price hits
$40: I sell 10% of what I acquired at under $1. Perhaps I buy a new car, and a tv finally.
Price hits
$400: I sell 10% and buy a house.
$4000 Retire from my job and go full time Monero promotion, consulting, activist. Sell 10% for travel and living expenses over the next several years.
$40,000: Sell 10%. Start a video game company (dream of my youth).
$400,000 Sell 10%. Now comes major charity work such as the gifted and talent orphanage, plus humanist endeavors such as cryonics research (don't worry Hal, we ain't forgot about you) and AI work.
$4,000,000: At this point we are among the richest people in the world, and personally I still hold 50% of the initial Monero I began with. At these levels, 10% would be a ludicrous sum, and with it I could likely get elected to any public office would choose, start a new country, cover Montana in sour skittles, build a replica of The Labyrinth, etc etc. This is where major contributions to humanity are possible. Luxury is boring by this point and wealth of this magnitude is mainly used to decide how humanity will focus its attention and resources. As always, connecting our species, seeking out talented humans born in suboptimal conditions, building AI, space travel, SETI, NASA, etc all become priorities.
I have already been toying with the idea of being more public in how much I own. I feel this provides some trust due to the fact that I serve in a slightly official capacity. Also, I hype the shit so much, it feels ethical to disclose that I am heavily invested. As far as malicious actors down the road, they can fuck themselves. You're welcome to look up how I handle a gun on YouTube, I don't negotiate with bad guys, and I fully believe in individual sovereignty. There will be much easier marks out there, I guarantee it.
I'm also considering some type of pledge... Like a pledge not to suddenly sell out of Monero for fiat during a bull market. Us early adopters will hold a lot of wealth if Monero does what I think it will, and those who come later will be assured by a public promise that a certain percentage of our Monero wealth will always be held in trust.
Ok, I confess. I've bumped up to 1MR for some additional caffeine. I need to clean the house and stop yelling at Bitcoin talk and day dreaming. I've got a girlfriend moving in next month, and she speaks Romanian so I told her a.) I'll have a clean house for her to arrive at and b.) imma put her to work translating Monero stuff into Romanian. Romanians are a good people, and I told her she might be the woman who helps make it one of the richest nations in the world.