Frisch gewagt ist halb gewonnen.

This is translated “Well begun is half done.” and I’m not sure if this is the best translation. It’s idiomatic or somewhat of a saying, but the English sentence seems to have a connotation of a task that needs completion, not necessarily a competition, and the sentence connotes that you’re doing a good job, but not necessarily doing anything bold or risky. Whereas the German sentence seems to connote a competition, and “gewagt” seems to connote that you’re making bold and perhaps risky moves. I’m really not sure how to translate “gewagt” here, but I think saying “half won” instead of “half done” would be an improvement.

I.e. the current English sentence here leaves open the possibility of something “mundane”, “boring”, or “straightforward”, whereas the German sentence is definitely not open to this possibility.

English Translation

A good start is half the battle.

According to deepl.com, it translates to ‘A good start is half the battle’, I’m assuming its a form of encouragement, along the lines of; maybe you’ve got a massive and daunting task in front of you and it’ll suck but getting in there, getting started is half of the struggle, just keep going.

English Translation

Well begun is half done.

Seems closer to ‘He who dares, wins’, perhaps?

I would say the meaning is pretty much what Havarthr wrote.
German also has “Wer wagt, gewinnt”, which is a bit different.

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