To Plan or Not to Overplan, That is The Question

Freedom of voice and freedom of choice are big themes in life anywhere. Here in America, they are imperative. Especially here in New York, where being a Type A person is a point of pride (necessity even) the themes of choice, freedom and control are safeguarded the way virgins of old guarded the maidenhead.

I admit, I’ve been that girl on occasion. I have a pair of those shoes, the Type A, scheduled and planned pair of shoes. We all know the shoes, and the girl who wears them so well. I’ve been her. The one who’s on the treadmill at 6:30, working with a trainer at 7, networking at a Park Avenue café by 8:30, juggling two consulting clients between 9:30 and 7 then meeting my beau at a Bowery Poetry Club reading featuring Yusef Komunyakaa. This New Yorkified version of me pops out at the occasional weekend too – out of bed by 8, coffee then a shower (yes, I take a shower before going to the gym!), a bit of cardio then yoga at 10, brunch with girlfriends, a bit of work on the non profit, cocktails with girlfriends then a late movie with my beau.

That pair of shoes, that girl – they’re fun and have a place in my world. But they aren’t my favorites. Yes, I cherish my independence and freedoms. Yes I am a strategist after all, so I like a good solid, well thought-through plan. Yes, I play out scenarios and prepare for a range of possible outcomes. But I also like to let the angels and the cosmos work their magic. Let the moon and the stars shape the fates. I like to hope, to try and read the signs.

I’m sure I’m not the only one in New York or anywhere for that matter who has some of that laissez-faire. The one who lets the traffic light changes get her from the Meat Packing District to Gramercy Park. The one who falls in love with shoes she can’t afford and says to them, “if you’re still here in 2 weeks then we were meant to be together.” The one who gets pangs of childlike wonder at the first star and makes that wish while whispering with eyes closed “Star light, star bright, first star I see tonight. Wish I may, wish I might have this wish I wish tonight.”

There is a sense of freedom to be found in letting go, trusting yourself and your own raw instincts; in giving in to a sense of the divine and magical; in spontaneity rooted in joie de vivre. Whoever said life was what happens when you’re busy making plans must have been some kind of prophet. My own life is a series of unplanned ‘that’s exactly what I needed’ occurrences from the beginning. I’m a honeymoon baby, I could not have come at the worse time. My parents got married in December and left for the US the summer that followed because Papa was starting his post-grad studies. Yes, I was smuggled into the country! When I was eleven I was accepted to an exclusive high school for the gifted which would have been the perfect plan for me, but I was uncomfortable with the idea and stayed in my school where I made some of my best girlfriends. I accidentally got into my career simply by being at the right place at the right time and asking the right questions. The list goes on.

So here’s the question, how much planning and scheduling is too much? When does planning the life get in the way of living the life? I am no less ambitious or driven than your textbook type A person, but I cannot spend my life planning my life either. What type does that make me, I wonder? I am clearly not a pure-blooded A, in the first place my blood type is AB. AB, what could that mean? What type could that make me? I checked online for possibilities, and found a good one: Aurora Borealis, the northern lights named for the Roman goddess of dawn and the Greek name for north wind. I like that, possibility and direction working in harmony. It sounds more like me, and you know what – I think I can even find the perfect shoe to match that vibe. Hmmm…I think I can sneak in a shoe shop between brunch and yoga tomorrow!

The Last Single Girl

I admit, I am a big fan of chick-lit. I have been for quite some time now, and I know exactly when it started. Mama first introduced me to Alice and when I looked through the looking glass, I found a world of wonder within myself. I have ventured into so many worlds since meeting Alice through girls like Nancy Drew and Amelia Jane, to Jane Austen’s Emma and sisters Dashwood and Bennet. As a grown woman, I have taken great pleasure diving into the world of Bridget Jones and finding as much in similar as I did different. The female experience is made of the same parts, now matter which part of the world you are going through it. On many occasions, stressful business trips were countered with the light touch of Jane Green and her animated women like Jemima J. I think my copy of that book is still at the Grand Hyatt Taipei, where I was a frequent visitor from 2003-2006!



I adored all these characters and the colorful, insightful experiences I vicariously lived through their stories, but there is one thing I do not share with them – I LOVE being a ‘single girl!’ To this day, six years into this relationship my beau and I still feel very much ‘single’ as we do together. There are parts of my single living that I would never give up, there is nothing I want to do now that I feel I cannot do because I am a dynamic, loving, monogamous relationship. In the last few months of my thirties, the thought occurs to me – perhaps I am The Last Single Girl. I am reminded of ‘Sex and the City’ and Carrie Bradshaw’s love affair with the gorgeous Aidan. Perhaps it wasn’t commitment she feared at all, but the death of her single girl.


This provokes the ultimate question, doesn’t it? Can a woman in a committed, monogamous relationship still lay claim to being a single girl? What about a married woman? Does sharing your life with someone mean the death of your single girl. We all recognize her, our single girl. She’s that girl who loves her independence and freedom as much as she loves the teamwork and sharing of her relationship. Over the past fifteen years I have happily witnessed my dearest friends finding love and marriage, building families and homes. I have cried happy tears for new loves, and bitter ones for the break ups. I have loved men, lost men, lusted men. I fell in love and continue falling a little bit everyday for the man in my life. And this heart that loves, it’s the heart of a single girl.

Is this a new brand of spinsterhood? The new twist to the proverbial old maid? Is the unmarried almost-forty of 2010 the re-branding and celebration of The Single Girl? Why can’t each one of us be that strong woman who loves herself as much as her beloved? Why does one’s personal ambition have to be at odds with shared dreams and a tandem adventure of discovery?

This year, I enter my forties still a single girl at heart. I suspect I might be the last single girl in my circle of women, and you know what…this makes me ever so slightly smug. But just a bit, until I realize that there are many sisters of my kind out there, strutting their stilettos. And thank the gods for that!