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emotional highs that you’ve been sustaining yourself on for years. Like a

junkie giving up the needle, you’re going to go through withdrawal when you

start giving these things up. But you’ll come out the other side so much

better.

How to Be a Little Less Certain of Yourself

Questioning ourselves and doubting our own thoughts and beliefs is one of

the hardest skills to develop. But it can be done. Here are some questions that

will help you breed a little more uncertainty in your life.

Question #1: What if I’m wrong?

A friend of mine recently got engaged to be married. The guy who

proposed to her is pretty solid. He doesn’t drink. He doesn’t hit her or

mistreat her. He’s friendly and has a good job.

But since the engagement, my friend’s brother has been admonishing her

nonstop about her immature life choices, warning her that she’s going to hurt

herself with this guy, that she’s making a mistake, that she’s being

irresponsible. And whenever my friend asks her brother, “What is your

problem? Why does this bother you so much?” he acts as though there is no

problem, that nothing about the engagement bothers him, that he’s just trying

to be helpful and look out for his little sister.

But it’s clear that something does bother him. Perhaps it’s his own

insecurities about getting married. Perhaps it’s a sibling rivalry thing. Perhaps

it’s jealousy. Perhaps he’s just so caught up in his own victimhood that he

doesn’t know how to show happiness for others without trying to make them

feel miserable first.

As a general rule, we’re all the world’s worst observers of ourselves.

When we’re angry, or jealous, or upset, we’re oftentimes the last ones to

figure it out. And the only way to figure it out is to put cracks in our armor of

certainty by consistently questioning how wrong we might be about

ourselves.

“Am I jealous—and if I am, then why?” “Am I angry?” “Is she right, and

I’m just protecting my ego?”

Questions like these need to become a mental habit. In many cases, the

simple act of asking ourselves such questions generates the humility and

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