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No. of Recommendations: 1
Have a single stock position that is accounting for to high of a percentage of the portfolio that i need to reallocate

This is a very high risk position. I'm sure you are well aware of your former company's products and markets and confident in them, as were many in the entertainment and leisure industry at the start of 2020. What I'm driving at is you nor I nor anyone knows what mother markets going to deal us next month. Being a high percent in one stock is just not a good idea, unless this is money you can afford to lose.

It sounds like you plan on your household income dropping significantly in 2021 from not returning to work? If so, I agree that I'd put off transactions until 2021, including re-allocating your company stock and doing Roth conversions. By projecting your income, you should be able to get an idea of how much in capital gains you can take and how much of your retirement plan/Traditional IRA value you can convert to a Roth and keep in the 10% and 12% Fed tax bracket plus whatever you pay in state tax.

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