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Something you wear, and wear again, is something you steadily wear. You do it so often, it's reliable. Also, if you wear something this much it's steadily wearing away too.
This word uses on'yomi readings of the kanji you learned, twice. You should be able to read this on your own.
着々と進める
to make steady progress
着々と進む
to proceed steadily
着々と進行する
to progress steadily
その会社員は、いつも着々と仕事をこなしていた。
That office worker always got tasks done steadily.
プロジェクトは着々進んでいるようだね。
It seems like you're making steady progress on the project.
そのプロジェクトは着々と進行しており、予定通りに三月末に完了する見込みです。
The project is steadily progressing and is expected to be completed at the end of March.
An update is needed before you can continue but you have more than one WaniKani tab open.
Finish up whatever you are doing on the other tab(s), then close them to continue.
The update will complete automatically once the other tab(s) are closed.