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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?

Turning 21, A brief letter to myself

On Striving For Happiness

I’m turning 21 tomorrow. I cannot believe how fast the years truly pass by. When I was in high school the thought of turning 21 seemed unfathomable. I thought I would be headed to medical school by this time and possibly dating my soon to be wife. Jesus Christ I was wrong. Instead I am becoming a certified teacher and am playing poker for a living. In addition, for the next few years I plan to play the field, learn immense game and date dozens of women.

Turning 21 makes me wonder where I’ll be when I turn 25, yet a lone 30. What would my 40 year old self tell me to look out for? If I could write myself a letter when I was 16 I’d tell myself to get my shit fixed that I need fixed. Also I’d tell myself to stop taking everything so seriously and join an improv class, take up a hobby, spend time outdoors and even spend more times with my friends. I’d tell my freshmen year version of myself to stop wasting so much time and spend it being more productive or with friends. Also I’d tell myself not to give involved in a relationship which would stagnate my growth for entire year and a half.

So far things are going pretty well, I have a full scholarship and am graduating a year early. I play poker for a living and am becoming pretty competent at pickup. I have a handful of truly awesome friends which I appreciate. I honestly still do not feel like I know truly who I am or where the hell I should be going in life, but I’m figuring it out one step at a time.

Thank you to my friends, particularly Allan for always motivating me. Without him I would have accomplished much less

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