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How I Learned to Stop Overthinking Things

A valuable mental checkpoint.
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When I was younger, I used to be incredibly hard on myself whenever I made a mistake. It could be something as small as burning a batch of cookies or as large as accidentally hurting someone's feelings, but I'd still be kicking myself for it hours (sometimes days) after the fact. One time, in my early twenties, I made my first big work-related mistake. I went into my boss's office, crying over the mistake and expecting her to be equally disappointed in me, but instead she asked me, "Is this something you'll remember in a year? If not, it's not worth being upset over." When I couldn't remember the exact mistake—only the advice she'd given me—a year later, I realized how valuable her words were.

The question provides a simple way of quantifying the "small stuff." Since then, I've made thousands of mistakes, but it's empowering to be able to acknowledge them and assess how much of my attention it actually deserves. To this day, I still ask myself that question as a checkpoint whenever I'm upset over something: "Is this something you'll remember in a year?" If the answer is no, which it often is, I let it go—that simple. 

I'd love to hear, do you have any tricks for not over-thinking things? Let me know in the comments below.

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