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If you could do it all over again

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I didn't go to college, but the day after I graduated high school I moved to NYC full time the next day. Up to that moment, I had been living in NYC only on the weekends.

What I would do differently would be to take classes at a city college. Probably in the field of teaching. I really liked my job I had after high school (buyer for a record store). I met a lot of great people and went to some amazing concerts.

I would step away from the roulette table after being up large $$. I wouldn't lose contact w my friend Damon. I would visit my sister at college more so I can bang more of her friends and piss her off.

I would see Frank Sinatra's and Nirvana's last concerts in NYC (both which I had tickets for but did not go).

I would continue using the boxing instructor I had, but will refuse to do sit ups (because of the strain it caused on my neck from doing them improperly).

I wouldn't have tried so hard to incorporate a certain high priced escort into my daily affairs.
 
If doing it over means changing anything about my life today i would not do a single thing different. If youre saying i could do it over and pick and choose aspects of my life, id do whatever makes me millions of dollars, bang 10s, own awesome shit and end all war. Stupid question.
 
I would immediately get into an addictions treatment program. Instead of pissing away my free university education, I would kick ass with my studies and instead of a lifetime of working in warehouses, I would be an astrophysicist. Or at least something.

The other thing that comes immediately to mind - depending how the rocket scientist thing works out - is when the online gambling thing starts up in the early oughts, I would be aggressive as hell instead of my cautious, keep-a-low-profile approach.
 
I probably wouldn't bother with college, but that's a tough one.

There was no educational value there that I couldn't have easily gotten on my own. Everything about it that wasn't school I remember fondly. But the actual work was stressful to the point that I still can have the occasional bad dream about being behind in schoolwork.

Professionally, I would move on from playing poker MUCH earlier than I did. If we go back with knowledge of future betting markets, trends, etc, of course I would make be able to retire in no time, but I don't think that's really the spirit of the question.

As far as interpersonal stuff goes, I'd like to think that going back, knowing what I know, I would be better to people and that would be better for me as well. Just a couple pretty large regrets that I think I could avoid the second time around, even without specific knowledge of them.
 
Yeah relationships are a tough call. As far as people I look back on as significant in my past (other than family), it makes sense that I would not even meet them with my new trajectory. So most of those specific regrets - and there are a lot - wouldn't happen.

But I feel like I would do a lot better with the relationships I would form. That condition of "knowing what I know now" is pretty huge.