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Translation of "çıkmalıydım" in English

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Examples of using "çıkmalıydım" in a sentence and their english translations:

Daha önce yola çıkmalıydım.

- I should have left earlier.
- I should've left earlier.

Ben önde iken çıkmalıydım.

- I should've quit while I was ahead.
- I should have quit while I was ahead.