Paying off Debt while Juggling Competing Life Priorities

Before I focus on gathering all of my debt documentation to get a true assessment of how my debt breaks down, I have some fine points to work out.

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First, I have a confession to make: I have already been working a second job, for almost five years! I average about $10K a year in net income from this job. Up until now, I have used the money to fund family activities and to buy clothes and holiday gifts. And earlier this year, I began planning to use the money to fund a big Caribbean vacation in 2020. I have always thought I was doing the right thing – I pay my bills and debt first from my 9-5 and because I didn’t have a lot left over for fun, I got a second job.

A major question is how much of an emergency fund I should save while paying down debt. I have read Dave Ramsey and I am familiar with his steps. And countless bloggers in the debt free community suggest that an emergency fund of $1000 should cover most of life’s unforeseen problems. Even after saving that amount, I still felt like we wouldn’t be secure enough, because my household expenses are almost $5000 monthly. So I am opting to save at least $5000 before devoting all resources to paying off debt.

I also started investing in the stock market at the beginning of this year. I own about 20 shares, over 4 different stocks, with a total value of roughly $2000. While this isn’t much, I have seen 2 of my stocks increase almost 50% in the time I have owned the shares. This leaves me conflicted about whether or not I should sell the stock and use the money for debt repayment.

I have to admit, the idea of shifting that second income over to debt repayment is also difficult to accept. My regular job is comfortable and sedentary, but my second job runs into the early morning hours. I’m on my feet the whole time, up and down on ladders, on the floor and in some dirty areas. The idea of doing all that on minimal sleep, just to give the money to someone else is a concept I am not yet able to fully accept.

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All that being said, I do realize that I need to make significant changes to my current spending and saving habits, in order to be debt free.

So, do I need to sell my stock to pay off debt? How much of my second income should I commit to debt payoff? How much of it should I be able to use toward keeping my sane on this long journey?