paths

There is a thought that when a goal/want/etc is especially challenging that one should perserver because it will be worth more once achieved. But what if the challenges and obstacles are in place to make you think twice about the decision or perhaps "hind sight" rearing its head in the present? As anyone who knows me well knows that my mind is rarely at rest. Since I have too much time to think during this huge mess that has become of my NY lease, I have been going over what a pain in the ass it was to get this place. It was myself who did the majority of the leg work, acting as the responsible party to make this dream of living in NYC happen.
Did I force fate into giving me what I thought I needed? I look back at the purchase of my first home and reflect on the many hours of work, phone calls, and money that it took just to get into the home. The lender said she had never seen someone work so hard to get the loan closed. Buying that house was a mistake. Along the lines of housing, my thought move naturally towards my loft. Oh, my beautiful, much missed loft. It was the first place I looked at to rent and was approved the same day. When I decided to purchase the whole transaction was smooth as glass and finished in two weeks. Aside from the leaving of boyfriends, it was the best decision of my adult life.
Speaking of old boyfriends, one thing Matt loves about me is that I see what I want and I go after it. My relationship with him is an example, this new job, seeing the world, living in NYC... But now I am at a place that I don't know what I want or what my next step should be. I think about the future and become overwhelmed. I have made the childish decision to live month by month and placing a new holiday in each just to have something to look forward to. My personality, the one I have put aside for this job is the control freak that would love to know exactly what I am supposed to be doing.
So, now do I just look for the easy road, the one with no uphills as the correct path? Do I continue to go after what I think I want even if it is the rockiest path of all? Or do I sit back and wait for fate to deal me into the next game?