I’m sitting here tonight contemplating my prospects: a stone wall or a way out? 15 years ago I started a magazine that I threw my entire self into. All the bits and pieces, shards and stories that I’d accumulated over a lifetime. I had been pregnant with all those random voices, ideas and opinions for so long and finally gave birth to them in that publication. It was fierce and funny and thumbed its nose at conventional wisdom. It became so successful that I sold it for an amount of money I thought would help me grow old disgracefully carefree. Then the stock market crashed and so did my money–easy come, easy go for a grasshopper. It always seemed like play money anyway after being broke for so long. So I stayed on with the magazine because I was still in love with it, drew a good salary, watched the new owners grow it into other cities and then watched it change. From what I hear, the change part is a pretty standard story. As Ani diFranco says, “If you want to challenge the system, don’t go to bed with it.” Now I’m in bed with the Man and the romance is gone, but the money is still good. I wish there was an arrow pointing me in the right direction. This way to the Next New Thing. This way to Creativity. This way to Big Ideas. But how will I know when it’s time to leave? And will I have the courage or juice to make it out there in a younger, hipper world? And should I even try? Maybe there’s a natural time to quit striving. When I bought a new Honda several years ago, a friend said, “That car will last you the rest of your life.” I was aghast, so as soon as the warranty was up, I bought a new one. Damned if I was going to stick with a car just because it would last me to the grave! Now I wonder if I’m sticking with a job just because it will last me til retirement. I feel as if not all of me is being used, and at the same time, I feel used up. Which one of those is right, or are both of them? Do I give up safety, travel, cashmere sweaters, more travel, new computers, expensive wine, Lucky jeans in order to set off down an unknown road that may in the end not lead to Big Ideas, Happiness or Fresh Starts? Do I leap and trust the ideas will be there to catch me up, or do I leap and land on Bag Lady, Dementia and Spending all Day in my PJs? Despite starting my own business, raising kids on my own and putting up my own frigging Christmas lights, I’m not courageous, and not even mildly outrageous–I need prodding in order to move forward and I’m more comfortable in corners than on top of the bar. I’m not proud of that. I wish I could be one of the women I admire who are so gutsy and confident and just pregnant with themselves. They move to cities where they know no one, they travel HAPPILY by themselves, they spend Christmas on Christmas Island just because it’s there, they go to Buenos Aires to tango. This Christmas morning, I wish I would find a big blue arrow pointing to Sure Thing, but I know it’s not going to be that easy. I guess I’ll settle for a Kindle…just in case I hit the road this year for a trial run.