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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?

Finding Your Roots

On Portland: Small Town Girl in a Bigger City

All through your teenage years you feel so very grown up. I remember all the anger and rage and frustration with the world I had during those years. Then I turned 18, started attending college, setting on into the next phase in life. The anger drifted away gradually and I found a whole new set of problems. Any friends I had who weren't 18 yet began to joke about how old I was, it felt like I had stepped over some invisible line that instantly made me "old." In hindsight, I was so very silly during the ages of 18-21. I wanted to be more than I was and didn't know how to find my place because I didn't know exactly what I wanted. My friends in college didn't have jobs and were riding on scholarships or parents paying for everything; they'd only talk about homework and college activities etc. I tried to go this route and couldn't grasp how to study since I had never really learned proper studying techniques in high school, and so I did the best I could.

I was told to get a job and felt indignant about it because my friends didn't have to be working while they were in college, but I got a job anyway. After that it became a battle of finding time for myself, finding time for work, finding time for homework and trying to get myself to class on time. It's a tough thing to learn how to do. I didn't figure it out until my final year of college, at which point I finally felt achieved and was sad to be graduating. College had, at long last, become fun and rewarding.

When I turned 21 I moved out of home. My dear friend had a place and she let me live there. I got my rent paid, went to class, and was fairly irresponsible as I tried to be the person I dreamed 21 year olds are. I had never really fit in anywhere, I was determined to fit in with this age group.

Every year since my 21st I have felt even older and older and farther and farther from my life goals. I want to find a partner, have a small cottage, have a child and work on my art. I graduated college at 24, lost my boyfriend, miscarried, and lost my apartment. Over the past year and a half I've been trying to climb back up but I took so many pit falls and wrong turns trying to find something to make me feel as together as I felt when I was on a path to my life goals.

In an effort to get myself together after I hit rock bottom, I made my initial decision to move to Portland. I had been talking about it for some time before I made the ultimate decision to do it. When I had first decided to move I found myself a boyfriend and put all of my plans on hold. When that plummeted into a burning hellfire and extreme debt issues I felt like there was no time other than the present to get on that move.

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