"Where do you see yourself in five years?"

Everyone has had to answer this on some bullshit job interview in their life. And you, inevitably, nervously sputter whatever you had rehearsed whilst pacing your apartment that morning; That you would like to lead a team. That you'd like to capitalize on this fantastic opportunity with this promising organization. That you intend to be the authority on some sort of technology or skill set. You say something, basically, anything that implies that you do, in fact, have this fabled plan, and that this particular company (and not the one you interviewed with yesterday, or tomorrow) is whom you envision it with.

But all too often, you're out the door after your first annual review--

And the grand promises you made that day in an HR office were just a means to getting your well-heeled foot in the door.

That is, I guess, unless you are me.

I graduated college in 2006 from a little University perched atop Beacon Hill. My business degree, with an emphasis on marketing, looked splendid on paper. I had also taught myself the basics of web and graphic design; enough to slap Adobe Photoshop and (what was then) Macromedia Dreamweaver onto my skill set section of my resume. I figured I stood a pretty great chance of landing a job that would utilize these skills, that would challenge and thrill me, and that would pay me as much, if not more, than what I was making waiting tables by the Garden.

Of course, none of this happened within the time frame I (or my parents, for that matter) expected. I graduated in June, continued to sling drinks till August, and then picked up a six-month paid "internship" for an IT security company based in the 'burbs, 30 minutes away from my South Boston apartment and still college-bound friends. The commute sucked, the product bored me, and I sat in a cube. This wasn't at all what I had envisioned. I kept waiting tables for both the money and the sanity.

A week before Christmas, my internship was nixed and I was basically politely pushed out the door. 

I packed up my desk with shaking hands and, strangely, no tears. Despite being a perpetual mess of emotion, I recall an odd sense of lucidity leaving that office park that afternoon, never to return again.

It just...was never meant to be.

And I wasn't going to agonize why not.

I made it through the holidays and then began my job search again. Pouring over Craigslist. Debating every word in my cover letter. Completing phone interviews in a locked bathroom because I lived with loud roommates. Tweaking my resume for every job post to be sure it was just right. I thought this was all so imminent. Surely using "Best Regards," to close my email would be the deciding factor in my employment status. It just had to be.

And then, something happened.

My dad emailed me a link to a job listing on Craigslist that had been posted a whole ten minutes earlier. I had taken a brief job search break to nurse a hangover and toast a bagel, when I returned to my laptop and checked out the post.

"Do you like Myspace?" it read (keep in mind, this was 2007), "Would you want to do something like that for a full time job?"

And that was it.

Simple. Perhaps a touch cryptic. But I knew all that I needed to know. The answer was a resounding yes.

So, of course, as it turned out, the company was MocoSpace, and I was applying for a role as a Community Manager. It was an entry level gig--one that surely didn't even require a degree or a technology addiction--but I came laden with both, and the unwavering idea that I was not only going to work for this company, but that I was going to work up it as well. Two weeks into "managing" the community (a somewhat euphemism for porn police, as we were deleting unfavorable user generated content some of the time, and keeping the site safe for users all of the time), I was throwing myself on any design projects I could get my hands on. Six months later, once we hired VPs of departments like Business Development and Marketing, I hung on their every word. I allowed every question that sprung into my Bud Light-saturated, twenty-three year old brain to flow out of my mouth before wondering if I sounded green.

I was too curious to care.  

Managers began to clamor to take me out of CM and move me over to a business role. This was met with some resistance from my boss at the time, he didn't want to lose a team member. Much less one that used the product daily, and was starting to understand the space. But I had to push it through. I was going to quit if I had to delete one more scandalous photo of a person taken with a Motorola RAZR in a dirty bathroom mirror.

And I couldn't quit. I knew there was still so much more to be done.

A year and a half or so after joining this team, I made my first title change. From Community Manager to Marketing Associate; I was suddenly working much more on design projects and an emerging feature: Music. I became the go-to girl for everything that needed to be done. I thrived.

I continued to support our VP of marketing for another year. We launched music and I found myself taking the Acela Express train to New York City once a month to lead live chats with Island DefJam artists. I met Fabolus, Rick Ross, Jadakiss, Hoobastank and more. I presented new ideas and was responsible for a whole feature set of content. I was excited. And inspired. And the envy of many friends.

But then something happened.
I fell in love with a boy in California.
And I wanted so very badly to join him, and his mattress on the floor in North Hollywood. I needed him to function. And as I sat at a desk in downtown Boston, three-thousand and fifty-two miles away, I began to become complacent. Distracted.
And sad.

The story of Matty and I is another long one, for another time, but it is imperative to note.
What he did for me, and my career, will have an effect on me forever.
He realized my job was "too good", the opportunity was too palpable, and that he, too, needed me to function.
He moved to Boston in 2009 to be with me, and that changed everything again. I didn't want his relocation to be in vain. It simply couldn't be. My tenacity resurfaced, and again I switched departments within my organization.

I became an Account Manager for our VP of Business Development shortly thereafter. I took on relations with all of our partners. I was immediately out of my comfort zone and was shedding tears behind my monitor on a daily basis. I didn't know what I was doing, and after a few years of high praise and comfortability with my role, I did not like that feeling one bit.

I remember talking to my boss at the time over Instant Messenger and he attempted to placate my concerns: no one knew the product, nor these partners, as I did. No one could be doing a better job. But I wasn't convinced. I continued to rattle in my insecurities whilst cranking out as much work as possible to compensate. It worked. I became comfortable. I became knowledgeable. 


That boss since left, I bid my adieu through a veil of tears to one of my initial mentors. He always believed in me. I was nervous his replacement wouldn't be so charmed.

But in walked our new SVP of BizDev a few weeks later, and the first meeting we had, he posed a question:
"What're you gonna do after this? I mean--where do you see yourself in five years?"
I laughed. I had had tunnel vision for what seemed like forever. And in the startup space, five years is not guaranteed. A month is not guaranteed. And I knew that.
"I'm not sure," I told him, completely candid with this then-stranger. "I guess I am figuring it out."

And now as I sit here, with the word "Senior" in front of my title on my business cards, that is the best I can do. I am eternally thankful to be a part of a startup; that I haven't been chewed up and bitterly spit out by some giant corporate machine. Or that I have never had to consult a dress code in the morning. That my questionable language has never landed me in an HR office (not that we have one of those, either) and nary a Friday goes by that there is not a beer on my desk at 3PM.

Above all else, though, I am grateful that this company has thrown me into the driver's seat of my career. I have never been herded into a position or pushed to make a choice. I have always been encouraged to carefully weigh my options, and let them know "what I want to do". Imagine that.

This "little gig" I landed out of college has brought me to the offices of IDJ, Sony and MetroPCS. To a Porsche Sport racing track in Alabama and a hotel suite with a basketball court in Vegas. It has also resulted in many late nights, my face illuminated by the glow of a smartphone, working from my bed.

I would not trade this experience for anything. And while I still don't have an answer for that whole loaded "five-year" question, I do know that in five years, some things will remain the same:

I will approach every opportunity with the curiosity, thirst and unwavering optimism I have maintained in five years here.

If that is my only plan, I would say it is a solid one.