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The line between impossible and huge effort possible goals?

Question from a reader -

Hi! Interested to hear your thoughts about this: where do you draw the line between impossible and huge-effort-possible goals?

First, I'll be honest. I don't have a perfect neat answer for this that's epiphany generating... I'm going to try to work through it on paper, and I appreciate feedback from everyone in the comments if you have related ideas.

Let's get started. First and foremost, I can't say this enough - study history! If you don't study history, you don't know what's possible. Period. You need to study history if you want to know what's possible.

Here's some good people to brush up on. Now, most people's reaction is, "I couldn't do that! He did so much!" But trace their steps, these men often came from humble origins and suffered much. Don't say "Wow." Ask, "How?" How did they do it?

Are you ashamed to be a man?

On Alan's Journey

How often have you pretended to ignore the beauty of a woman because you're afraid that you'll be 'caught out'? How often have you avoided telling a woman that you like something about her femininity (if she has any, that is) because you're afraid you'll be labelled as sexist? How often are you made to feel that it's a crime to be a man?

If you're like most men, the answer is probably A LOT.

This is what society tells you, of course. It tells you that being a man is a shameful thing, full of indignities against women.

I knew a man that used to be punched in the arm by his wife if he so much as glanced at another woman. So he wore sunglasses all the time so that she couldn't see where his eyes were going.

I knew a man that begged his girlfriend to let him go out for a few drinks with his friends, but she refused to give him permission so he went home with his tail between his legs instead.

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