The wisdom I've encountered on BF to this point is truly mind boggling. You all have some great perspectives on things...
Visiting my grandfather recently did put a lot of things in perspective. He had a hard life, but even when he thought he might die he had no regrets and looked back on his life with a smile. I too have had some challenging circumstances, but I always make the best of my situation, always see the positives, and in general, you won't encounter too many people that have a better outlook on things than myself. I am not disgruntled, and I am not going to make any rash decisions. That is part of the reason that I am so thankful for all the feedback that I've received here. If I do anything, I want to think it through first and do it intelligently.
Someone said it well. I don't want to end up being 65 and look back at my crossroads in 2011 and regret not trusting my gut and going for it.
Pros and cons...
If I continue on, I know what to expect. I will work 55 hours a week or so for the remainder of my natural life, most likely get a house in Southeastern WI with the woman I am currently seeing, be the financial provider for her and the family that will come after she bangs out a couple of my kids, and I will grow old without ever truly experiencing many of the things I would love to explore in the world.
If I just go, I have no idea what's in store. I don't know where I'll go, what I'll encounter, how long I'll be gone, or what condition I'll be in when I come back... if at all! I have no idea if I will be able to maintain a lifestyle that keeps me with minimal possessions while I am constantly on the move, seeing and experiencing the many amazing things out there. It is completely unknown. Therein lies the heart of the decision.
True financial wealth is complete freedom to do whatever you want. Without true wealth, everything is uncertain.
One is the smart and conservative decision. The other is a gamble, and one that will most likely NOT lead to any sort of financial security down the road. It's a risk, but all of the world's most amazing people take them, and all of the best stories come from people who took a chance.
I am wrestling with this in my head endlessly. Your words have been very helpful.
Jordan