Sep 9, 2026 · 11 min · 8 segments
If I asked you to name the skills that make teachers successful outside of the classroom, you might say something like communication, or curriculum design, or organization, and those are real. We…
And this is a big one because I think it quietly wrecks more transitions than we realized.
Teachers are trained to be the person in the rooms with answers, the one people go to.
You're the one who plans, who problem solves, who doesn't get to say, I don't know, in front of 28 nine-year-olds.
We learn to be the one who's in charge, who's making the plans that people follow.
This instinct is not helpful when you're trying to switch careers because here's what's happened.
They tell maybe one person, a spouse, let's say, and nobody else because it feels unfinished or embarrassing or like admitting defeat if it's not all figured out.
And I think this is the downside of becoming a very competent teacher is when we do things where we feel less competent, i.e. anything new.
And so the people who actually get somewhere, they ask for help before they feel ready to do so.
Teachers haven't practiced being the one who doesn't know the answers, but that discomfort is so important.
And this is a big one because I think it quietly wrecks more transitions than we realized.
Teachers are trained to be the person in the rooms with answers, the one people go to.
You're the one who plans, who problem solves, who doesn't get to say, I don't know, in front of 28 nine-year-olds.
We learn to be the one who's in charge, who's making the plans that people follow.
This instinct is not helpful when you're trying to switch careers because here's what's happened.
They tell maybe one person, a spouse, let's say, and nobody else because it feels unfinished or embarrassing or like admitting defeat if it's not all figured out.
And I think this is the downside of becoming a very competent teacher is when we do things where we feel less competent, i.e. anything new.
And so the people who actually get somewhere, they ask for help before they feel ready to do so.
Teachers haven't practiced being the one who doesn't know the answers, but that discomfort is so important.
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3 of 5
Rejection Is Data
A rejection can reveal what to change.
Stop Figuring It Out Alone
Career changes begin with one uncomfortable step.
The Imperfect Opportunity
Your next role may not look perfect.
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