The Job Seeker's Dating Game

Imagine the following scenario:

A young woman is at home, getting ready for a first date on a Saturday night. She’s picked out her outfit and just jumped out of the shower, about to put on her makeup.

As she gets dressed, her thoughts drift to who she’s meeting – what he will look like, what questions he will ask her, and how she might answer.

Above all else, she wonders, will he like her? And will she like him?

As she approaches the restaurant for dinner, her hands shake a bit and her heart pounds in her chest. She introduces herself, makes eye contact, and takes a deep breath.

During dinner, she thinks it’s going well, but she’s not quite sure. He seems to like her, but then again, who knows?

After dinner she says good night, and that she hopes to see him again soon. He says the same, and they part ways.

For the next few days she waits by her phone, hoping it’ll ring. She checks her email frequently, and when she doesn’t hear anything, she starts to get nervous. Finally the phone rings, and it’s him. As she goes to answer, she wonders: does he want to see her again? Or is this it?

You might be wondering why I asked you to visualize this first date experience (and I can bet my husband is definitely among you!).

The reason is simple. Over the last few months I have come to believe in one simple but powerful truth:

Looking for a job is, in many ways, the same as looking for love.

You might think this is an oversimplification, but actually I don’t think it is. To start, take the above story and change every dating reference to an interview situation instead. It’s not a Saturday night, but a Friday morning. She’s not going to a restaurant, but an office building. In most ways, the thoughts, questions and nerves are, in fact, totally the same in both scenarios.puzzle piece window

Trust me, I know what I’m talking about here. As you may know, I’ve been on my own job hunt for a little while now, and throughout it all, I’ve been struck by how often it’s felt like dating.

The reason? It’s all about fit.

Ah yes, fit – that elusive, yet all-encompassing three letter word that sums up just about every job search process. Just like in relationships, when it comes to job searching – and more importantly, receiving and accepting an offer – it’s all about fit.

Like looking for love, finding the right job is a process that takes time. Sometimes you find a job that fits right away, and sometimes (ok, oftentimes) it takes longer than you’d expect.

Everyone has dreams of finding that one person to spend their life with. And while finding a job in the short term may not be nearly as important as finding “one true love,” it can be easy to put just as much pressure on your job search as you do on dating.

Unfortunately, after a few unsuccessful attempts, finding the right fit can feel next to impossible.

Take another example. Throughout my job search I’ve had my eyes on one thing and one thing only. I’ve been specific when it comes to the type of work I want to do, and the people I wanted to work with. This has been, in effect, my own version of Tall, Dark, and Handsome (as in, Ladies – what kind of man are we always looking for? Tall, Dark and Handsome of course!).

What I’ve learned, however, is that what I think I want is not necessarily what’s best for me, or what will make me happiest in the long-run (in dating terms, we often call this “going after Bad Boys”). Like looking for love, what we say we want in a job and what we actually want in a job can often be very different things.

Recently my homework assignment has been to think about what I am really good at and what I really enjoy. Rather than labeling it with a specific job or industry title (my own professional version of Tall, Dark and Handsome), I’ve been trying to think more broadly about what skills I have that I enjoy using.

What’s amazing is that when I am honest with myself about what I do well and what I enjoy doing, suddenly so many other doors swing open. Industries I’ve never considered, job functions I’ve never thought of, and opportunities I’ve never looked at suddenly seem interesting to me.

All of a sudden, finding the right fit seems possible again.

I once heard Ami Dar, founder of, talk about the interview process for new hires at Idealist: “I wouldn't propose marriage after the third date,” he said, “so why would I hire someone after only a few interviews?”

While every job seeker wants to find a job as quickly as possible, ultimately finding the right fit is important for both sides and it's something that takes time. When you’re honest with yourself about what you’re looking for, though, your odds of success – whether in work or in love – can only go up.