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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?

My Definitive "Meaning Over Happiness" Post

Mike Radivis just asked asked some good questions on "Chase Meaning, Not Happiness" -

How do you measure meaning if not in terms of happiness? Aren't things that create more happiness for a longer time for a larger number of individuals better than those things who lack those qualities but are proclaimed to be personal achievements anyway? Does the scope of happiness make happiness meaningful to you or not? What are achievements good for if they aren't good at facilitating happiness? Imagine you wouldn't experience any pleasant or unpleasant emotions and would have to decide rationally what to pursue (assuming that is possible at all). Then what you want to do with your life? (Another way to formulate this question maybe would be to ask what's your grand strategy in that situation.)

I'm quite interested in your answers. I like that your blog posts are so outspoken. It's just that the message of this post is hard for me to grasp, as I'm pretty much utilitarian in my thinking.

Good questions. I'll go through it line by line.

How do you measure meaning if not in terms of happiness?

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