School or Not School

I'm back to thinking again.
I keep thinking about my future. You know, life after Japan? I keep going back and forth on the issue of more education and if so, do I immediately pursue a Master's or should I seek a second degree and then get a Master's in something else?
If I choose not to further my education, will I regret it? Also, where should I live? What should I do? Will I make enough money?
This decision is not an easy decision, but I feel the pressure to make it soon. As a woman, education is essential. But if I pursue a second degree, a Master's and possibly a PhD, I would finish in my late 30s or early 40s. My fear is that I will be too old to be hired. In my case, I truly believe that age is just a number. I am a hard worker and I am young at heart. A great combination, right?
While a 4-year degree is nothing to be ashamed of, I feel the need to have more. I think that I am more marketable by having a higher degree.
I come from a family who has always told me "It's not what you know, it's who you know." I agree that it helps to know people, but if you don't know anything, you don't have much help either. My family has also instilled in the womenfolk that we will marry someone who will take care of us. If we get an education, it's something to keep us occupied or we can get us a "little job" to help with some extra income. most of my family has quit vocalizing this to me, but it continues to be communicated non-verbally. I have serious issues with this mentality.
First of all, I am not set against marriage, but I do think it's important for men AND women to learn how to take care of ourselves. There is NOTHING wrong with supporting myself!
Second, I would hope that if I marry, that man would respect me as I would respect him. I would hope that we could communicate enough to support each other's careers. If it came to a point where one of us had to choose to give up their job, I would like to think that this is something that could be discussed rationally. Rational thought does not assume that I (as the female) must automatically give up my job.
Third, I would very much like to retire some day. The way I see it, is that (again, assuming I do actually get married) two people saving together is better than one. Rather than fighting and running each other down as you are aging because you don't have the savings that you thought you would have (only one of you was working full-time), why not work TOGETHER?
These are just thoughts.
PLEASE NOTE that I am not against marriage and I am not against mothers who stay at home. I am simply trying to dispute my own family's views.
I think that I consider myself old-fashioned in some ways, but I also am not naive enough to think that every woman is going to get married. Or that every husband is able and/or willing to provide for his family. I also realize that, even if I adhere to my family's thinking, I have not yet met the right person to marry to take care of me and my parents aren't going to take care of me until I find someone. That would be ridiculous!
So I say that I would like to have the opportunity to buy a house some day. I would also like to be able to travel when I have vacations. I would like to be able to work a full-time job with benefits and have a 401K.
Sure, I have ideas of what I would like to do. Now comes the hard part. Do I go back to school to pursue a degree in something that I would really love to do (even though I would be putting myself further in debt)? Or do I look for a job without further schooling? I am sure that there is something out there for me and that I just don't know what to look for yet.
I also have a tendency to doubt my abilities. The thing is though, that I think that I am a hard worker, well-rounded and a quick learner, so I'm sure that I could do a lot. I would just need for someone to take a chance on me.
Whatever it is that I decide to do, I feel the pressure to start researching now. If I choose to look for a job right away, I need to start working on a resume soon. If I am looking at schools, then I need to research all of my options. There are deadlines and requirements for admissions. Also, if I choose a Master's program, there may be requirements for the GRE.
Either way I choose, it's a gamble.