It's challenging when dealing with millions of dollars. $5 million is a substantial amount, and a 37% capital gains tax would reduce it to approximately $3 million. Essentially, you would lose $2 million to taxes.
$5m is life changing.
Having said that it is stupid to commit tax fraud and live a life of perpetual fear.
This is where people lose perspective. You're not "losing" anything. If $2million is owing on $5million then the $2million was never yours to "lose to tax". The $2million was always owned by the government (assuming it is calculated correctly).
The mindset that tax is losing money or being taken from you is I think at the heart of why some people go tax crazy.
It's easier to deal with if you don't ever see it as your money, cause its not your money.
You made $3million and part of the cost of making $3million is $2million tax.
Focus on the $3million. The $2million in a real way does not exist to you.
$5m is life changing.
Having said that it is stupid to commit tax fraud and live a life of perpetual fear.