“Where do you see yourself in five years?” he asked me.

I had thought this was a date, perhaps, and then it started to feel like a job interview. I sipped my glass of wine and gave a number of cheeky answers followed by a few of the five-year ideas that spin around in my head. I added more to the answer a few hours later.

I get asked variations of this question often recently, and my answers are usually in the same direction every time, but they’re not concrete. Still, since he asked me I’ve started to ponder it seriously.

As he said later, “one cannot think about one’s five year plan too often”.

See, I used to know exactly what I wanted. Granted, teenagers think they know everything – but I really did have some five year plans in mind.

I was fourteen the day I started college and when people asked me what I wanted to do, I told them I wanted to study law and politics and run for state representative four years down the road. I wanted to move up through New Hampshire politics all the way to Governor, where I’d facilitate the great libertarian experiment – the Free State Project.

I wanted to make a difference, you see, and I was an idealist.

Then I met a man who I came to love, and he was the kind of idealist who doesn’t believe in anything anymore because he’s been too exposed to the harsh realities of compromise and selling out. He didn’t want to poison me, but it was a thought process I hadn’t really touched before, so I was fascinated by it. He drove a wedge of doubt into my idealism, and to this day I’ve never been quite sure whether to thank him or curse him for it.

I considered applying to Harvard. At the time I was in my second year of college (at fifteen), I was achieving good grades in everything but my mathematics class (I’ve always been terrible at that), and I’d just received a “Rising Star Award” from my favorite professor. Then I decided I didn’t want to leave New Hampshire. There were other factors, and I occasionally begrudge various individuals for their hand in convincing me not to even try, but I simply decided that I didn’t need to leave New Hampshire to be successful there. I could stay in New Hampshire colleges, work New Hampshire jobs, and be successful as the libertarian politician who did it all “the New Hampshire Way”.

I applied to Saint Anselm College, got accepted and attended in 2005. I didn’t like it for a variety of reasons and moved onto the University system of New Hampshire.

I met a new man who I came to love, and he lived in Boston. Suddenly I found myself meeting interesting and creative people who didn’t simply philosophize about perfect situations but made their own lives full and inspirational. I split my time between New Hampshire and Boston, found dissatisfaction in my political factions and began to cultivate an interest in intentional community.

My worldview got a little bigger and I started to think I really wanted to be the person organizing things, making alliances, getting my hands dirty, not standing above it all – suddenly I went from idealizing being the politician to being the staffer – I wanted to be a libertarian version of Josh Lyman from The West Wing. If I was willing to do politics at all. The passion was starting to leave.

I also became aware of something random and somewhat unrelated – that many of my amazing friends were in their 30s and without children. It was my observation that in this world the people who are reproducing [at the highest rate] seem to be the ones who are too ill-educated or religious to use birth control. Suddenly I realized that if these incredible individuals don’t have kids, their values of compassion, tolerance and progressivism will only get as far as they themselves reach, and not necessarily impact the next generation.

Suddenly a footnote attached itself to my five year plan – something like “find agreeable man, have babies, teach them values”. Not necessarily sure the babies needed to show up in the next five years – but I knew I’d be interested in finding the man within the next five years.

Then I fell in love with a new man. This one had dreams of living all over the world and reaching people through his (brilliant) musical talent. In one fell swoop, pretty much, he cracked open this bubble I’d intentionally enclosed myself inside, and he said “there’s a whole fucking world out there and you’re twenty years old. Go see it before you decide what you want.”

So I moved full-time to Boston and we planned to move across the country together. I figured I was good at selling political ideas (and retail items, professionally), I could sell his music and get into creative marketing there. I started to promote not just his work but the creative works of all my talented, incredible friends. I knew what I wanted – in five years I wanted to be his date at the Academy Awards where he’d just written a nominated film score and I was observed by the media as the woman whose skills at networking had gotten him his big break. I knew I wanted his kids someday, so there I was, just living a dream – we were doers, we were movers and shakers, and here was the world, we’d take it by storm.

I’ve been in a constant state of declaring what I’m going to do with my life for the entirety of it – up until July of 2009. That’s when my heart was broken.

In that moment I gave up plans for the future. I thought I had it all figured out and it just kept changing. I was done being disappointed. I was done limiting myself and then feeling like I hadn’t accomplished anything when I looked back at what my five-year plan had been “then” versus what I wanted “now”. I was 21 and there was a whole fucking world out there for me to see before I decided what I wanted from it.

I packed all my belongings up, put my birds in a travel cage and I moved by myself 3000 miles away from everybody and everything I knew, to a city I’d been to for eight days one year before.

I feel like, on paper, I don’t possess a list of accomplishments. But I have all of these experiences, hurtling into specific directions with blinders on about everything else, allowing something along each destination to spin me somewhere else.

And all this time, I’ve written about things. Written about what I want, what I am, what I’ve done. The only consistent thing in my life is that I experience things with this self-awareness where I feel like I’m watching myself while I’m doing whatever it is I am.

And it’s from that place I write.

I don’t know what lies in store for me in five years. I’m interested in behind-the-scenes of the entertainment industry (blame living in Los Angeles for two years for that), or script writing, marketing, maybe reinvigorating myself into alternative politics, and probably writing about my current experiences in Las Vegas nightlife. I’m primarily interested in experiences different than the ones I’ve had already, or variations of those at least.

I feel like I’ve spent a lot of time declaring five year plans which limit my ability to see everything else. I feel like I’ve finally put myself in a position where I see so many options and I don’t know where I want to go next – I just want to see what comes my way. I like to think I’m extremely good at adjusting to change, and when that’s your talent, what else can you do but embrace constant change until you find something good enough to stick with?

Where do I see myself in five years? Not where I am right now. Not because there’s anything wrong with where I am, but because there’s a whole lot of opportunity for someone like myself, and I’m honest enough with myself to know that I don’t know what all is out there – so I can only open my eyes widely and take whatever steps lead to higher than where I am.

To sum it up – my five year plan is to have a five year plan in five years.