Should I sell individual stocks (taxable brokerage account) to fund my IRA?

[mtn]

I feel like this is a simple question, but would rather get the opinion of the hive here.

As part of my compensation package, I am able to divert some of my income to company stock, and the company matches 25%. So, if I buy 100 shares in a year, they give me 25 more shares. This is all taxable, so my income shows that I was paid the value of the 125 shares of stock (value as of purchase date, aka each individual payday).

These are not vested for a year, so I was just blindly putting in the max (who wouldn't want an immediate 25% return??? Not to mention our stock has been killing it over the past year).

I'm now coming up on the point where a bunch are vested, so I can sell them if I desire. I will be selling some of them to pay off a credit card before the end of the introductory 0% interest period (it was a mustachian decision, trust me).

But now I have to decide what to do with the rest of it. Options are, as I see them, the following:

• Sell shares ASAP and put into our IRA (not sure if we'd go TIRA or Roth in 2020)
• Sell shares and pay off our student loans, approx $10-$15k at 5.5%
• Do nothing, let them sit in my companies stock - not really comfortable with this, but this is a stable company and one that is probably "too big to fail" (actually, I know it is "too big to fail")
• Sell shares and create a cash emergency fund. Current emergency fund is only 1 month of cash, but between IRA contributions that could be withdrawn without penalty, collectibles that could be quickly sold, family help, and each of us having 2nd/3rd jobs, it isn't as bad as it sounds

If it helps with your recommendations, some background information:

• 30 years old
• Our debt includes our mortgage, a car loan at 2.75% that we are in no hurry to pay off, and the aforementioned credit card (0%, will pay it off before interest hits by selling the stock in question here) and student loans
• Including the company stock and our HSA, our total retirement savings is approximately 1.2X our income, and our savings rate is approximately 30% - it will vary between 20% and 50% depending on our side-hustles

[wageslave23]

definitely sell them after they are vested, you want to be diversified.  definitely pay off the credit card before you have to start paying interest on it.  deciding between IRA, student loans, and emergency fund is a little more tricky.  assuming you are in the 22% tax bracket, I would probably max the IRA first, you only get $6000 each year and if you miss a year, you never get it back.  then you still have time to decide if you want to pad your emergency fund or start paying off student loans.  the student loan interest is tax deductible or can be depending on your income level.  however, I personally don't worry much about an emergency fund because if shit hits the fan, like you, I'm confident I'll have enough sources to pull from.  so I would start paying down the student loan interest after paying off the cc and maxing the IRA. 

[mtn]

definitely sell them after they are vested, you want to be diversified.  definitely pay off the credit card before you have to start paying interest on it.  deciding between IRA, student loans, and emergency fund is a little more tricky.  assuming you are in the 22% tax bracket, I would probably max the IRA first, you only get $6000 each year and if you miss a year, you never get it back.  then you still have time to decide if you want to pad your emergency fund or start paying off student loans.  the student loan interest is tax deductible or can be depending on your income level.  however, I personally don't worry much about an emergency fund because if shit hits the fan, like you, I'm confident I'll have enough sources to pull from.  so I would start paying down the student loan interest after paying off the cc and maxing the IRA.

CC is definitely getting paid off. That was never up for debate, just putting it in there as some more information to our situation.

I'm thinking like you, I think we'll go ahead and do the IRA, then Student loans.