Yesterday I wrote about altering my plan to reach $1,000 a month in passive dividend income. This idea of redirecting my current dividends to the debt to pay it down faster also brought up the idea of just straight selling off my dividend funds to pay the debt off and restart the snowball from scratch.

I ran the math. At current value I’d be able to claim a $3,000 loss on capital gains for 2026 taxes. This would net me $825 between Federal, State, and City taxes, while also saving me from $2,350 in interest across these two debts. As you can see at $500 a month in dividends, I would net negative $3,000 a year. Now, ideally I would be able to take my paychecks and work on building this back up as quickly as possible. The issue is that it still doesn’t math out in my favor.

If I’m capable of adding $2,000/month to the snowball, then that same amount added to the debt plus the $500 from dividends still nets me an even bigger win over buying more dividends. With my 15 funds plan I was still going to be at only $700/month off of $49,000 in principal. Which is the same amount of money I need to add to pay off this debt.

While I’m hoping to pump more than $2,000 a month at this debt, the way life is going this year, I think that might be too ambitious of a plan. If I can put $1,500 a month at the HELOC, $500 at the Car, $500 from dividends to the HELOC, $500 from Covered Calls to the HELOC. HELOC payoff date is 7 months at $454 interest. Then 5 more months for all of that money to finish paying off the Car. This would produce a total of $1,080 in interest.

This is a reliable plan that I hope I can escalate with more payoffs. In order to get my windows and driveway done at 50% cost due to the city grant, it must be done this year. Which can increase my HELOC balance again. So here’s to hoping my math works out.

~~Miniwing~~
Loving Math