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I have a question I need some advice with.

I've been getting options from my company for five or so years now. I feel a downward trend in the stock coming soon. So my question is do I sell the most recent options that I received that I will have to sell more to reach say $40000 or do I sell the earlier ones that I will sell less shares for the same dollar amount.

I'm guessing that part of this answer depends on what I feel the longterm health of my companies stock is. Since some of the most recent stocks I've received expire 5 years later than the earlier ones.

Any thoughts would be great.

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