Hi! I have about $15K in investments, $8K in an HSA, and am $10K in debt. I know my investments are there for the long-term but I want to get back to my debt-free status. I’d love to hear differing perspectives: if you were in my shoes, what would you do? Thanks!

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The optimal answer is it depends on the rate of your debt, how much excess cash you can generate per month, your expected return on your investment, and the tax on gains if sold today.

If the investments are sitting in a taxable brokerage, your tax hit would be minimal, and the debt is high interest then yes it likely makes sense to sell and knock it out, especially if you aren't making much progress paying it down month to month. If you'd have to pay tax on significant gains, the debt is low interest/less than expected returns on investments, or you could knock it out by buckling down for a couple months then probably not.

The fastest route out of debt is to sell your investments and pay it off immediately. If you take that approach commit to then building an emergency fund and not letting yourself get back in debt (other than a mortgage, maybe car loan). If you don't, you'll likely end up in the same debt situation within a couple years with no investments to bail you out.

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