<prompt> Human: I am notoriously bad with money, I just have no mental connection with it, its like a block for me. I stress over a 5.00 convenience item and yet just spent thousands fixing my poorly constructed deck without a thought. I have a lot in the bank. Over 750,000. mostly over the years profits and the sale of a business I worked very hard atI have a new mortgage, it is now at about 260,000k 15 year, 370k loan at 3.9 apr, put down 100k 2500 per month payment.I fully realize that keeping and paying the mortgage over the next 14.5 years costs me a lot of money but I am scared to death of losing a huge chunk of what I have all at once. I am a bit older not old and I have no desire to go back to work for someone and honestly, if I entered the job market again my computer skills are probably so far behind Id end up a wal-mart greeter.Currently I have all my money just sitting in a checking account. I am scared to death at being out of money in 10 years and not having anything to fall back on some day except SS if its still around I have this notion in my head that if I pay it off and something happens I will be completely screwed. I realize I am an idiot and I am asking for advice. I know 500k is a lot, but it really isnt if you are not planning on going back to work in the next 20-30 or so years before my probable demise.Do I pay this mortgage off right now?Is that the right thing to do?Before you answer, again, I realize I am a personal finance idiot, and in a privileged position, so be gentle.Updating: I am in my early 50s and I also have 100k in an IRA Update 2: To everyone.. thank you for the advice!, I should have made it more clear though, I am not looking for work. not now anyway I have worked the last 30 years 60-80 hours a week.Assistant: Your money is not gaining any interest at all on a checking account. If your only options are keeping it in a bank and paying off the mortgage, Id pay off the mortgage since its interest rate is higher than the return youre currently getting.The more reasonable choice would be to keep paying your mortgage and invest most of that money. On average, the returns would be much better than either paying off your mortgage or just keeping it in a single bank where most of your money is not insured by FDICNCUA. Human: I can get better returns by investing and paying the mortgage?I just did the math lol I think2500 x 174 months 435,000If I pay off the mortgage now it costs me 260k, so I save 175kI can make that amount or more in investments over 15 years with 750k dwindling by 30-50k per year? If so that sounds great, I am not sure where to start to make that kind of return :Assistant: Your monthly payment doesnt look correct. I have a new mortgage, it is now at about 260,000k 15 year, 370k loan at 3.9 apr, put down 100k 2500 per month payment.Was the price of the property 370k or was it 470k? It sounds like the property cost 370k, you put down 100k, and then have a mortgage loan of 270k.Are taxes included in your monthly payment? A 15-year mortgage for 270k at 3.9 should have a monthly payment of 2k.Human: 600 is for taxes and insurance in escrow.  <response>: Yes, but thats irrelevant -- youll have to pay taxes insurance whether you have a mortgage or not. 