<prompt> Human: Throwaway account as I cant afford to have this found out by anyone ever.I have a close friend who I feel could really use an unsecured and unsolicited 50,000 life loan from me. Now before you share your caveat or favourite horror story of how wrong this could go, please read my string of mitigating details that just maybe puts this in the region of reasonable. Guy was a US Marine Corps veteran and pilot who graduated top of his class literally 1st in 900, he was slated for an all star career when after 10 years at domestic bases or whatever theyre called, he had a change of heart based on grounds of conscience. Since then he worked sales at a startup-stage Netflix and as a DJ before having been fully self supporting and self employed for the last 10 years. Ive worked with him and lived with him on several different ventures, everyone in our industry considers his integrity unimpeachable. Ive given him a 20,000 loan in the past, although he lagged a bit in repayment it was mostly because I didnt press him about it or care very much. Many others have trusted him with similar amounts, usually for some sort of business transaction but on occasion as an outright loan.How hes gotten to this situation: Our industry has been dying for a number of years. 90 have quit, only the cream of the crop have any chance of survival and he is finally struggling to keep up while making diminishing returns doing so. Its also an industry that has little to no transferability of skill to anything else i.e. no resume value.The guy is creative, good problem solver with engineering type stuff, mostly construction but he is getting into software as of late, go-getter, relentlessly persistent at anything he sets his mind to, and has excellent people skills and intuition. His main leaks are that he lacks attention to detail and is quite disorganized especially with managing time. He can also get real impatient and even impulsive when under pressure. For example he has recently been proposing increasingly outlandish schemes in fields he lacks the necessary experience or relevant contacts to have any chance of success in. Part of this is he has no understanding how undetailed his schemes are, partly I think asking me for a straight up loan is a bit humbling given that I am about 10 years his junior, and we were once equal business partnerspeers. He has succeeded in his line of work which I always thought was a poor fit for him IN SPITE OF these leaks. Right now he has about 20 grand in the bank including liquid business assets. Obviously no drugs or other addictions.I basically want to loan him time. Time to figure shit out and possibly set the course of the rest of his life. Its a sizable dent in my own bankroll, but not life changing in the least.There will be zero interest as a matter of principle. I am undecided on repayment period. I am considering a conditioning of the loan around the idea of tried and true. As in there has to be a plan such as going to school, getting a license in X field, etc. to which any individual use of the loan money in excess of 300 must contribute in some way from paying rent to tuition money to buying tools and equipment for the trade in question. Im undecided on the specifics or how detailed the conditions and checkups ought to get, given this is a close and trusted friend. But I do not want to invest in any of his schemes. I just want to set him on a stable career path.Thanks very much for your advice, will post updates.EDIT: I really appreciate all the input, some of the personal feedback is a little lol as I didnt actually paint the whole picture above there is actually a big favour I get out of this up front and I enjoy the full benefits of this prior to the loan. I just wanted to focus on how this would improve his life. Yeah I came to the conclusion independently that if I did this, even if he accepted which is not a shoo in fairly likely he rejects my conditions and digs in to his schemes even more he would perma resent the attempts to regulate his life even if ultimately seen as for the better, and forever wonder whether scheme X would have panned out. As hard as it is to say, guy just needs to fail and learn some lessons on his own imo. Anyway thanks again for sharing your thoughts and hope they are relevant to anyone else out there considering something of this sort.  <response>: Ive given him a 20,000 loan in the past, although he lagged a bit in repayment it was mostly because I didnt press him about it or care very much. Many others have trusted him with similar amounts, usually for some sort of business transaction but on occasion as an outright loan.Any individual who regularly relies on very large loans from his friends, for any reason, is a financial train wreck, no matter how faithfully he repays. Most people use banks or, as a last resort, family, and most people dont borrow 20,000 at a whack for anything except a car. His is a bizarre fiscal profile, and it is not that of a person you want to be involved with financially. 