I’m sure I’m going to get eaten alive for this. I can’t seem to ask anywhere without a bunch of assholes coming out of the woodwork or perhaps my wording isn’t right. I live off what we will call a “trust fund”. I have an actual trust fund, but at the moment it’s pretty much make a phone call when I’m broke. This all worked out great when I was younger. I blew a trust fund when I was 18, got too used to living like my mother and being way too comfortable never learning the importance of money and have been cut off from direct access to money. That being said my spending is still grossly unacceptable. It finally hit me sometime this past year that I can’t continue on this path for the rest of my life. I sort of went into panic mode and have been floundering about trying to figure out what to do. I’m financially ignorant, I think milk is $10-20 still. I’ll happily admit it but also the reality that it’s not healthy, not sustainable and generally looks bad has hit me hard. I can change my lifestyle, but that alone won’t be enough. After blowing through multiple millions simply having the money invested won’t be enough. I can invest some of it more aggressively. I can work, as for what , who knows. I have had jobs when I was younger. I had a promising young career at one point but injury struck and that dream was crushed. I have no problem with hard work, I simply haven’t applied that to my financial situation in years. I did join the military out of HS but any discipline gained has melted over the last 15+ years. I’ll be totally honest, I don’t even know how much money i would need to “retire”. I don’t want to get too personal with what I spend now, what’s left, what I’m willing to live like etc. I don’t know how to talk about that without coming across like “that guy”. (If I haven’t already) Is posting something like: “I live off x-y per year, I have roughly A and B left invested and liquid. What are some main points you would consider when trying to solve this problem” acceptable? I’m curious if after reading this anyone with some significant financial experience is willing to let me ask several specific questions I can’t find solid answers for w/ Google. I’d also love to hear any financial advice or experiences people have been given/had. I’m at the point where I will listen to anything. My life also influences a family member, as well as my wife obviously. I don’t / can’t have kids so that is not a concern. Edit: I can’t be the only person who is in a somewhat similar situation. I think any advice could be mulled over and used by others even if not in exact same shoes.