Leaders don't aim for perfect. They simply try, experiment, fix, recalibrate, try again, strategize, find what's missing, dream bigger, work at it (maybe a bit harder this time), break some things, fix those things, do it all over again, try better, and then finally they get where they'd like to go.
Take the very old discipline of kintsugi as an example. When a piece of pottery is broken, it isn't discarded, but rather rejoined with gold. The break is noticeable, but there is beauty in it. The breaking is now a reminder to try better or different or harder or more carefully next time.
James Altucher experiments often, trying new things as a method of learning (even if many of them don't work out).
In order to grow quickly, Facebook developers were told it was okay to "move fast and break things."
If, as a leader, you're not trying something that could be important because you're afraid of breaking something (or failing, even), then you're not cut out for this.
Breaking can feel bad, like we're failing. But the act of repairing is an act of leadership.