I should on myself a lot.
I should be a size 4.
I should be in graduate school.
I should be a better mom.
Shoulding never gets me where I want to go, because should asks the wrong question. It asks, "what will please everyone else? What do they expect?"
It doesn't ask the right question: "what can I be?" Or better yet, "what am I already?"
A couple of years ago, I did something tremendously brave, I wrote a list of things I wanted to do, no one else. Just me.
They were big things and little things, stuff I wanted to accomplish, things I wanted to try, things that scared me, stuff that just sounded plain fun.
I made a shift from shoulding to doing.
My cousin Cheryl told me this formula once, of how you grow towards a goal, and it can work both ways:
I want to be a writer, so I must write.
I want to gain control of my fiances, so I need to have the right tools.
It's not Be-Should-Have or Have-Should-Be.
Healthy striving has very little to do with shoulding.
Healthy striving has a lot to do with doing.
Two big things about this shift, from shoulding to doing.
First big thing: shoulding takes A LOT more mental and emotional energy than actually trying to do the thing, whatever it is. Shoulding is a kind of low-level, buzzy, insecure energy-drain. After doing the thing, I was just genuinely tired. But happy & satisfied. Maybe still a little raw or sort of scared, depending on what the thing was (looking at you, essay submissions and subsequent rejections).
But I did it.
There's only one way to build confidence--do the thing and get the outcome you want. Or close. Or not at all. But try try try. Yoda was a little bit wrong: "do or do not, there is no try." Sometimes there's only "keep trying." Do the thing, try to do the thing, so one day you can ACTUALLY do the thing, whatever YOUR thing is. You'll learn a lot for your next attempt.
Second thing, and this is the bigger thing, the biggest surprise of my 30s: When I stopped trying to be who I thought I should be and just started being who I was, people found me delightful.
So, stop shoulding on yourself. Go do you thing. The right people will find you delightful.