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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?

Why I Work

On Ideas in the Making

NOTE: Work in this case means anything that is done for money, not necessarily explicitly for money, but done with money in mind, as a component, or as a tool in. Of course work has many definitions and I don't even completely agree with the one stated above, but I needed a word that would articulate what I wanted to represent without being verbose.

After spending the last few years reading just about every major hack-the-system, be productive, quirky blog out there that tells you to start your own business, or become location independent I've realized that a lot of them resonate with me, but aren't really what I want. Take for example Tynan. I love his blog, the fact he finds innovative, different, quirky ways to solve problems. The gear he picks is some of the most niche, and effective gear for getting the results he wants and fit very well into his ecosystem. He has cool stories and spends a lot of his time (especially as of late) becoming extremely productive and getting a lot done. But lately I've been noticing a trend in many bloggers focusing on creating things bigger than themselves, leaving a legacy, and so on and so forth. They work because they want to solve a problem in the world, or they want to leave something behind, or they want to create something greater than themselves. I have nothing against this personally, and maybe I am still too shortsighted to see the benefits of it, or maybe I'm missing something, but that isn't why I work.

Ultimately I've realized I work because I want to be able to afford not to work.

The truth is while I don't hate work, I hate not being able to afford not to work. Its funny cause, this very characteristic is what drives many, if not almost all top performers. Top athletes can't afford not to exercise and train, top programmers can't afford to spend long amounts of time not coding. Sometimes it isn't because of the money, many top athletes could very well stop training and exercising and be able to live very comfortable lives. Sometimes its that "I don't know what to do" factor. I mean if you think about it, if you spent years after years having the goal of becoming best or very good at X and you finally reached that goal, after expending vast amounts of time, energy and attention reaching it, it would be incredibly hard to separate your identity from it, and in some cases you would even feel guilty or have a sort of mid-life crisis giving it up, as happens to many top sports-stars.

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