When does it make sense to cut your losses and wait for a better price to enter again in the future?

When you can predict the future

This seems to come from a trading point of view, which I could possibly assist to provide some generic guidelines(there are specific rules that I utilise but will take quite a bit to explain):

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1) When prices are below your buy price

2) When the reason you bought it is no longer valid (price fell back below the breakout etc)

3) Price drop approx 7 to 8% (A portfolio decrease of 10% will require 11% return just to breakeven, and a 20% decrease will require 25% investment return of the remaining just to breakeven. Think about this)

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While I mention about the price drop of 7-8%, it is not a drop of 7-8% of my portfolio as I do position size into every position of a stock, risking no more than 1.25% of my entire portfolio.

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Hope the above helps.