Learn Turkish: Keşke gençliğimde daha çok cesaretim olsaydı ve ticarete başlasaydım. - I wish I had more courage in my youth and had started commerce.

The pattern for past regrets is keşke (I wish) + verb + -se/-sa (conditional) + -ydi/-ydı (past). In this sentence, we see it twice: olsaydı (had been) and başlasaydım (I had started). Because they follow keşke, they combine to mean "I wish [it] had been" and "I wish I had started."

If it translates to "I wish I had more courage", why doesn't olsaydı end in -m for "I"?

Because in Turkish, you don't say "I have courage"; you say "my courage exists." The "I" concept is already handled by the possessive ending on cesaretim (my courage). So, cesaretim olsaydı literally translates to "I wish my courage had existed/been." That is why the verb olmak takes the third-person ending (-dı) instead of the first-person (-dım).

Can you break down the word gençliğimde (in my youth)?

It starts with the adjective genç (young). Adding the suffix -lik turns it into the abstract noun gençlik (youth). When we add the possessive suffix -im (my), the final k softens to ğ (gençliğim). Finally, the locative suffix -de (in/at) is added at the end: genç-liğ-im-de.

Why is there an -e at the end of ?