‘I partially support my partner of 12 years as his business is, sadly, failing’: I’m 33, and have $300,000 in company stock. Should I sell those shares to pay off my debt of $56,000?

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‘I realize I will have to pay some fairly large taxes due to the gains on the stock, so I need to factor that into the sale as well.’

Dear Quentin, I am 33 years old, I currently make just over $120,000 a year, including an annual bonus, and my company has gifted me with around $300,000 in equity in the firm, although our stock is brand new, so it is constantly swinging up and down. I put around 6% toward a 401 and another 4% toward personal savings, investments and emergency cash.

The big question is, should I sell my company equity to pay off my debt? Or, should I continue to pay off my debt and allow my stock to grow? I realize I would have to pay some fairly large taxes due to the gains on the stock, so I need to factor that into the sale as well. Thank you so much for your input, and thank you for your column.Dear In Debt, You’ve come a long way in a very short time. The median salary in the U.S.

“Your student-loan debt was clearly money well spent, and your personal and credit-card debts make up a smaller proportion of your overall debt.” “Your debt level of $56,000 is manageable considering your gross income, and asset values; however, you should review the loans’ interest rates and contemplate paying down these amounts, especially where the interest rate — and the interest costs does not appear to qualify as tax deductible — is in excess of the investment return on your assets,” he says.

Sometimes, it’s hard to let go. But doing so could result in the sale of the business, enlisting a new business partner, a co-investor, or even starting a new venture, Speiss adds. “In considering these suggestions, the preservation of your own income and assets are critical. If the business were to cease, you could still assist him to cover his bills and expenses.”

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