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Pay off Debt by Selling Investment Property?

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    #16
    Yes, yes you should.

    It's really that simple. Now, you don't necessarily have to sell everything at once, but I highly recommend doing a spreadsheet of your debts - all payment amounts plus the amount of interest on each. Calculate how much you are ACTUALLY paying when you include interest, and it might make you woozy with how much money you're wasting.

    If you have lease agreements on these things, there may be time limits so you can't get out of them soon, but the second you can, do it. You can replace these things later, or even check out message boards (like Craigslist or Freecycle) where people may be giving away old cameras and old mountain bikes, for instance. If it were me, I'd start with the biggest problem which is likely the car lease (especially as you're then also getting rid of gas, upkeep, and insurance payments). But you're basically right now in a state where you have the appearance of wealth (or at least comfort) but no actual wealth, and if you don't take care of this bad spending habit now, it's only going to get worse. I highly encourage you to take stock of the situation and minimize everything. You may be surprised how soon you can afford to buy these things outright after getting rid of the lease and interest payments, and of course you won't have to worry about making the really important payments for your company - which is a huge red flag. If you're skimping on your company's payments in order to have fun stuff, you're playing with fire as it is and in danger of losing the company and everything along with it.

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