Waiting until we are fully prepared can delay learning experiences. A conversation, a new job or a simple change of habit rarely comes at a moment when all the circumstances are arranged.
This does not mean that mistakes should be sought or their consequences minimized. We can prepare as much as is reasonable, try and leave room for correction. The value of the attempt also depends on what we do when its shortcomings become clear.
Life doesn't have to constantly seem like proof that we have everything under control. There is room for pleasure, uncertainty and learning in the same day. Accepting that can make it easier to participate, instead of constantly procrastinating.

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