Going through the American meritocracy you are expected to believe one powerful "truth": if it's not perfect it sucks. If it isn't the right answer, then it's the wrong one; if it has a flaw, it's flawed. This guides most of your life. But as you well know, nothing is perfect, and that includes you and me as human beings.
There's a heavy toll you pay for getting stuff wrong. It's mostly levied by those who monitor your moves (bosses, family, nosy neighbors). Sometimes we lay the punishment on ourselves as our most vicious critics. Imperfection, and it's cousin, "being wrong," are things you'll have to hear about again and again.
But being perfect--or even thinking you can be--is dangerous. "Perfect" is an illusion, a theory that can help motivate, but only when you know it's only a theory. Seeking perfection without reminding yourself that you are human and can err & break can drive you to frustration and destructive self-criticism. Without a doubt, you will fail (at least once), and you will be told that you are wrong (at least once). What matters is what you do right after, how you heal your wounds. The chamomile for these moments is being kind to yourself.
Know that you will not get it right the first time. And that's totally OK.
Know that you will get something wrong somewhere down the line. And that's hella fine.
Know that there's still tons more to learn. And, guess what, that's cool.
Know that everyone else is half-drowning like you are. It's true.
Know that your walking skills are still pretty good, despite your various stumbles and trips.This is what being kind to yourself looks like.
Most people, unfortunately, are more inclined to boo rather than cheer, because it's easier to see the fails than the greatness-in-progress. That is why you always need to be your most undeterred, annoying, and faithful fan.
How often should you to be kind? As often as you don't see it around you, and as often as you cringe at what you just did.