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The other mistake I often make is letting tax consequences control the process.

I hear this argument from many investors and my answer is simple. Up to $480K gains are taxed at 15% rate. First of all, if your gains are more than that, stop complaining, be thankful, say a prayer or do something good, because you are blessed. Separately, You would be better off paying 15% tax than taking 50% (it doesn't have to be 50%, it just rhymes)haircut.

None of us stopped going to work because we are paying taxes on our income. I am not saying you should not plan taxes, but find the balance. Optimization on one should not lead to overall sub-optimal situation, this is true for software design and true for life.

Good luck.
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