09/24/2014 11:40 am ET Updated Nov 24, 2014

Overqualified and Underemployed: My Journey to Find a New Job

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Recently, I did something I thought I'd never have the courage to do. I quit my job without a back-up plan. Soon after, I began sending resumes to companies that were in line with my interests and past experiences. I had a pretty good start. I received email replies, which led to phone calls and in-person interviews. I asked intelligent questions and had fruitful conversations with HR about my qualifications. I felt good about my skill set and was confident I would be negotiating my new salary before the week's end.

However, after several days, then weeks of radio silence, I received polite emails informing me I had not been chosen. Though I knew I shouldn't have, I scoured the websites of the companies that had rejected me to see who was ultimately hired. To my horror, I saw that the hired candidates had less work experience, had graduated from less prestigious universities and were all around less impressive candidates than I was. I was baffled and distraught. Did I have some sort of twitch that came out during interviews? Had I forgotten to email a thank you note? How had these inferior candidates gotten a job over me?

With nothing left to lose, I emailed one of the companies that had rejected me. "I have a bit of an unusual question for you," I wrote. "Can you tell me why you didn't hire me?" The response was short. "It was so great chatting with you. We felt you were very aligned with our company's mission and culture, but we felt you were overqualified for the role and would not feel challenged in the position."

There it was. I hadn't been rejected because I wasn't good enough. I was rejected because I was too good. It was like being turned down at the dance because you were too pretty, or rejected from Harvard because you were too smart. Who were they to tell me what I was overqualified to do? I had taken the time to apply, given an enthusiastic interview and followed up -- it was clear I wanted the job!

The whole process reminded me of college applications. I had gotten rejected from my safety school, the school your guidance counselor tells you to apply to as a backup. The school you are 100 percent supposed to get in to. I remember storming into his office, rejection letter in hand, only to have him explain that some schools did not accept overqualified candidates in order to make room for students that would actually attend. In a classic dating move from my early 20s, the university had rejected me before I could reject them. It seems employers hold a similar mentality.

I spoke to Patricia Schwardon, a career counselor, to gain some more insight into today's hiring practices.

"HR's job is to eliminate applicants," she told me. "If they are looking for someone with two to three years experience, and you have five to six, in their eyes, you aren't qualified for the job."

Most likely, an overqualified candidate will feel less engaged and won't want to stay at her position, Schwardon said. An employer doesn't want to hire someone they know is too good for the job, because chances are the candidate thinks so too. Overqualified candidates tend to stay in jobs shorter and often require hire starting salaries.

Still, it didn't seem fair. What if I just really wanted the job? Should I dumb myself down? Lie about my job experience and lower my GPA a few points? Did I need to be mediocre just to get a job I knew I would be good at? Yet perhaps this was the problem in itself. Was I setting my goals too low? Was I not challenging myself enough in my job prospects?

I talked with Lisa Speransky, an entrepreneur and current head of marketing at BEABA, about her extensive experience interviewing candidates. She shed some much-needed light on my predicament.

"Hiring is a lot like dating," she explained. "It has to be the right moment for both of you."

Comparing my job search to dating actually made sense. One was entering into a relationship that had the potential to be mutually beneficial, but only if both parties had clear expectations. If a young company was looking for someone in a support role, and my end game was rising to a managerial position within said company, then neither of us would be getting what we wanted. Just like finding that special someone who shares your values and desires, an employer wants a candidate that wants the job advertised, not someone looking for the next best thing.

I realized that much like New York's frustrating dating scene, being transparent about goals and expectations is key in finding the right job.

Remember that time you told someone you were dating you were fine with a casual thing but really wanted a long-term commitment? I sure do. What I remember most is how badly things ended, and how much easier it would have been to be honest from the start. Call me a romantic, but I have hope that special job is out there. It's not too big and not too small, and when I find it, it will be exactly the right size. Mine.