First step: when to leave

So I guess that the biggest question that I have to answer/ choice I have to make right now is whether I want to leave in two months, which will be in the beginning of November or four months, which will be in the beginning of January. There are definite pros and cons for both departure dates.

If I leave in November, I will be able to meet up immediately with my friend Dani from work, who is beginning her trip in Thailand with her friend at the beginning of November. I could also choose to meet up with my friends Anne and Dixie in the Philippians. This is actually the most enticing plan for me. Anne is from the Philippians and has family there, so she would be able to show me around, make sure that I am seeing all the most important places, and I might even have a place to stay. I have traveled alone in Mexico for two weeks, the first time that I had been out of the country, and I was not able to eat for most of the two weeks because I was so scared. For this reason, beginning my trip in November seems like the smartest plan. This way I would be able to ease into my mostly solo adventure. It would act almost as a crutch, a safety net of sorts.

Also, I don't really have much to stay for in Seattle. I have been here for over 7 years. The scene is getting old and is so small. The girls are killing me! And I am soon to be "homeless" in a month. I will be staying with an ex in a studio with 2 dogs and 2 cats for a month (we are good friends and strangely I truly believe that this will be a good idea), then I believe my best friends girlfriend will be taking my cats and I will live with my friend Maritza for a bit, or whoever will take me! With this being said, I might as well leave earlier, right?

Then there is January. The biggest draw for this departure date is that I have a lot of things that I have to do and small trips that I have to take before then. Kammy and I are going to San Francisco to learn how to sail, I should visit my family in Connecticut, and I should probably stay through the holidays and make as much money as I can before I go. I also love the holidays and don't know how I feel about spending the holidays in Asia. My favorite part of holidays is being with my friends and people I love and I might be too upset and lonely if I am in a foreign county for those special days.
I am also in school right now and the semester is done at the end of December. When I traveled to Central America for three weeks I was taking three classes. Luckily I had internet access everywhere I went, but it was not even close to easy to take tests and complete my homework when I would have rather been on the beach, or having fun. Even worse, it could have been like when I went to Africa, with unpredictable, slow, and hard to access internet. I don't think I really want to take my chances...but maybe. Plus, I think it might be fun living with friends for a bit...a Seattle Nomad