The Worst Thing to Say to a Cautious Personality

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Perhaps the only thing you need to know about my personality is:

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I failed my first driving test for “Granny Driving”.

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That’s literally what the examiner told me once I’d carefully placed my parent’s minivan into park.

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I’ve never gotten a speeding ticket. I would never dive from a cliff into a lake. I read my emails 12 times before I send them.

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I am the most careful and cautious person I know.

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And yet, when I do finally decide to take a new action (after endless self-doubt), the people who love me always react in the same way.

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“Are you sure?”

“I don’t know if that’s a good idea.”

“What if they take advantage of you?”

“Have you thought about...?”

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YES! I CAN ASSURE YOU I HAVE THOUGHT ABOUT ALL THE THINGS! THINKING ABOUT ALL THE THINGS IS WHAT ALMOST STOPPED ME FROM DOING THE THING!

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For some reason, my impeccable track record isn’t enough to convince them that I have good instincts.

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I think what happens is that since I’m SO cautious and predictable, when I do take a step towards something new, my loved ones are shocked. Perhaps they assume that since they often act impulsively, that I’m doing the same.

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Either way, they’re just trying to protect me.

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But it KILLS me.

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I’m learning, slowly, not to let their well-intentioned warnings stop me completely. But for many years, I took the “Are you SURE?”s as a sign to stop.

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It’s made it difficult for me to trust myself.

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Some folks hear “no” and react in the opposite way.

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“I’ll show you!!” they say.

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Not me. It doesn’t take much to stop this train.

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If you love a cautious soul, and you want to participate in their evolution, the best thing you can do is trust them.

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When they announce to you a new plan of action, instead of “Are you sure?”, maybe say:

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“I’m excited to support you through this.”

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Goodness knows they’ve thought long and hard about that first step.

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Heck, they probably rehearsed HOW TO TELL YOU ABOUT the first step.

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Encourage them to take it. Trust me- they’ll be forever grateful for your faith.

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