These are the Questions that Keep me up at Night.

Anonymous Teacher
2 min readJul 18, 2022

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Here are some questions I wrote to myself today. Questions that will undoubtedly keep me up tonight.

But hey, at least I’m asking them.

Have I really done my best in life? Or is that just something I tell myself to make myself feel better about myself?

Do I love my kids as much as I think I do? Or as much as they deserve to be? Or as much as they need to be?

How long will I continue to label myself a failure because I couldn’t make the marriage work?

Why do I love other peoples’ vulnerability, but dislike my own?

When will I give myself grace for making mistakes? Instead of thinking of myself as a f*cking mistake?

Will I ever be the man that God wants me to be?

Why does it feel like God is sometimes closer than other times?

Will loneliness always be my constant companion? Or will we go back to being acquaintances again?

When will I finally believe I’m worthy of love? Not because of the identities I carry, but because of the human being that I am?

Will I ever trust my judgment again?

Was I the husband I thought I was? The one I should have been?

When will I stop comparing my insides to other peoples’ outsides?

Why do I think the things I feel are unique to me and not universally felt by everyone else?

Can someone ever understand me if I don’t fully understand myself? Can they accept me unconditionally, even when I find it hard to accept myself?

Can I experience love when the thought of it sometimes terrifies me?

Will I ever fully experience what it feels like to be held in the arms of God?

Isn’t it a miracle that God loves us, even when we don’t deserve it?

Shouldn’t we consider ourselves lucky that His love is illogical and irrational?

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Anonymous Teacher

I’m an educator, writer, and single dad. I have two Master’s degrees and was teacher of the year. But honestly, who gives a f*ck.