Everything to lose is a bottled up expression of release while having lost everything means they have no reason to ever turn back. Everything to lose burns hotter but has a chance of stopping, while having already lost everything burns colder while being more consistent.
Beyond that it depends largely on the individual. One guy who's lost everything can become super depressed while another who has everything to lose could bundle into a ball of paranoia.
"And if you can, do you believe one man could hold both of those titles?"
I don't think so. Even if they have the means to get it all back, they're really manifesting having once lost everything as their motivation. One is being afraid to let go while the other one's already done it.
Edit: Come to think of it, the one who has nothing to lose is scarier simply from the consistency. You can't reason with someone who has nothing, while someone who stands to lose something can be reasoned with through that. All the one who's lost everything has left is that motivation, it's likely the only thing keeping them alive.
"beyond that it depends largely on the individual"
For philosophical purposes i'd like to imagine these two as equals, with the same extreme amount lost as the other has yet to lose.
"Come to think of it, the one who has nothing to lose is scarier simply from the consistency"
Consistency applies to both, as long as he still has something to lose that fire will be there.
"You can't reason with someone who has nothing, while someone who stands to lose something can be reasoned with through that."
You could by giving him what he's lost but that's beyond what I'm going to point out. I think if you're in direct conflict with someone who has that much on the line negotiation isnt an answer. He will come until he secures what is his. What I like to imagine in this case is the desperate measures a man will go through to get his family back. Considering the consistency(again for philosophic accuracy) is the same which is all possible.
I find the two as equals. They both have the ability to be unpredictable, limitless and persistent to the same degree if under the equivalent stakes of the other.
Edit: "I think if you're in direct conflict with someone who has that much on the line negotiation isnt an answer. He will come until he secures what is his. "
Of course you could just give him whats on the line, but that's not really negotiating. For the sake of concept itself I imagine what he has to lose can be bartered back to him.
I think you should stop trying to numb yourself, to make yourself impenetrable so that nobody could get to you or harm you, protection to a certain point is normal, yes you are beyond what society calls normal but deciding whether to acquire something in your life and either make it more valuable than your balls and protect it with them if you have to or make it more valuable than your balls and become emotionally invested in it then let it go so you could never be swayed by anything similar ever again isn't the smartest nor healthiest way to go, you might end up destroying yourself but finding no target to chug the broken pieces at.
I set high expectations to test myself and to keep me sharp, I plan my goals a significant amount above what I expect of myself. Sure some of my level of work my induce some numbing but I've already been numbed beyond that point and it wasn't by choice. I'm completely content with pushing my own thresholds at the sake of my own sacrifice. It's something that's been a part of my moral code for sometime now as well as it's something I pride myself on. Every higher trial I'm able to commit to teaches me higher degrees of self control, persistence and discipline, abstaining from physical wants and needs to achieve what ordinarily wouldn't be done. It may be self destructive to an extent but I find it just as if not more rewarding in personal growth and development.
Someone who has everything to lose may do anything to keep what they have, but someone who has lost everything is free to do anything they want. A person who has everything to lose seems more single minded in it's pursuit than the one who has nothing to worry about anymore.
Maybe the freedom's what makes it seem scarier to face? At the very least freedom makes someone more unpredictable.
"Man who has everything all about self preservation, this limits him in what he is willing to do and how he can do it."
Not necessarily, the limits of a man who has everything to lose are as high as the stakes are. Anything and everything will be done to reach that goal. When there isn't anything more valuable than what's on the line, there isn't a consequence worth fearing.
"If you have lost everything, you would most likely be willing to do anything for x goal if it is important to you but he would clearly have less resources at his disposal."
The man who's lost everything wouldn't have anything to hold back for, making his limits flexible and manageable. In this case consequences of breaking certain limits just simply aren't existent to the point of having a death wish. Fully willing and able to commit himself over 100% to any cause at any time of his choosing.