When to judge and when not to is already confusing enough, striving and resting in God is yet another paradoxical dual tension.
aka the tension line between faith vs reason/action.
The first question is, where did the anxiety/stress to strive come from? Well, everything has to come from the permission of God rite? So God has to part to play in the allowing that anxiety or stress to cause you to strive.
The second question is, is striving good or bad? How do we draw the line between when to strive and when to let God be.
Did God permit striving to allow you to reap the goodness of striving? Or did God permit striving to test you to lean and rest on Him.
We see that the wisdom from above is a paradox. Wisdom is almost incomprehensible because wisdom is dual in nature.