<prompt> Human: Some info about my situation: I am 36 years old, married no kids. I have 120k worth of liquid stock. It is actually not a portfolio per se, as its not diversified. It consists entirely of my companys stock via their ESPP program and accumulated bonuses. I contribute the max amount to this program, and it basically serves as our savings. I make 125k a year, and my wife another 55k. Our combined 401ks total around 65k 55k 10k, she started late. So did I, TBH. The balance on the mortgage is 125k on the first mortgage, and 24k on the second HELOC, both at 6 so high I know, but my home is currently under water and Im one of those that seems to have slipped through the cracks with the programs the govt has put out - make too much, not behind on payments, wrong loan provider I am less than 10 years into my 30 year mortgage.Other signficant debts: Student loans: 50k Car loans: 15kI am wondering if I should aim pay off the mortgage in its entirety, as it would be a huge relief to be a bonafide home owner and not have to worry about a roof over my head. Other options are paying off the other debt, and applying those payments to my mortgage to pay it off more quickly. Or paying the other debt plus just the second mortgage to get some equity, and trying refinancing for a lower rate. Im really nervous about having all that money in one stock, so I want to do something with it, just not sure what.I have read elsewhere in this sub that it is likely the most optimal to maintain a mortgage payment, and I am not looking forward to the tax hit with no mortgage interest to deduct, but honestly I cant stand being in debt - my wife and I are doing ok but the whole thing feels way too fragile.What direction do you think the numbers are pointing? Is it worth it to pay off the mortgage in one huge payment? Assistant: I absolutely would liquidate and pay much of my debt. Two reasons:1. Your mortgage rates are pretty high, and a guaranteed 6 return on my money easily beats out the risk of the stock market2. You are extremely non-diversified. Your livelihood already depends heavily on the success of your employer if they do poorly, you could lose your job, and you have only consolidated that dependency by choosing to hold stock in them as well. Unless of course any of your other loans are higher than 6. Id still liquidate, but pay those off first.Human: I agree with both your points. Would you advise selling everything at once, or stagger it to avoid an outsized tax burden as some here are concerned about?  <response>: Talk to a tax advisor, there are ways to diversify and reduce tax burden at the same time. 