Career Lessons from Dating


Probably one of the more fun articles I’ve written, I was ecstatic when Budgeting in the Fun Stuff let me reprint this article.  The original link is included, so check out all the great comments!  I’d been on a string of career-type articles, being added to a few Wisebread listings courtesy of Linsey Knerl.  ENJOY…

Parallels are all around us. Browsing the site, you may have already come across Financial Lessons From Engineering or Financial Lessons from Running, which made relationships to personal finance from other experiences.

Making the connections can be a lot of fun, and the more adventures we have in life – the more overlapping themes we’ll notice. The funniest part is, you’ll be surprised at where they pop up!

During a random thought session (i.e. waiting around for public transit), I was pondering my career history and future. A few simple keywords set off an explosion of brainwaves and, before I knew it, parallels to dating were drawn.

A lot of the story is still unwritten, but would guess most people will find similarities, and hopefully contribute even more!

First Love

Ahhh – remember those puppy love feelings? That first quick peck, bravely holding hands, and the thought “this is the one”. When we first start out, whether in our career or in love, we don’t know what quite to expect, so we cherish every moment. We’re idealistic, naïve, and content.

We may consider everything the company does as undeniable.
If someone was fired, then it was for good reason right?
We may think the company has our best intentions at heart.
If we work long hours, the company will take care of us right?

While its not impossible for careers to jump from First Love to True Love, eventually most of us realize “there’s more out there”. Probably some older, wiser employee educated us on the cruel, self-serving world of business and grand illusions of retirement send-offs faded away.

Before moving on, there’s an important point to think about. Not many people realize, but initially we are all trapped by convenience.

How many people’s first relationship was long distance? Or how many dated someone from another school? Good chance we all started out dating someone within biking distance of our school or house.

Thinking of career fairs at college, would it be realistic to think we’ll find our True Love company among the 100 or so there? Especially when there are 100s of 1,000s out there!? And what about our criteria for selection – name brand & salary? What about something more substantial, like company ethics or employee satisfaction?


After our First Love, we’re hot stuff right? The bars been set and now it’s time to reach higher. For whatever reason, there always seems to be this feeling of “doing better” – especially when we’re young.

The world is our oyster as they say. We think we’re experienced, think we know what we’re after, and reach for the sky. Who cares about the substance mentioned above. Let’s get the hottest, flashiest person/job out there!

In cases like this, we typically make concessions. We’re more willing to overlook faults because this is what we dreamed – and we want those dreams to match reality.

If we lie about our expertise, we’ll get the project and I’ll be flying 1st class for the next year. If we don’t, there may be negative repercussions on next month’s review.

Unfortunately, the reality eventually catches up with our dreams and we’re left with Heartbreak. And now we’re at a critical fork – do we maintain our fantasy, ignoring the reality or adjust our expectations and move on?


Instead of introversion and reflection, there’s this need to fill the void with whatever comes our way. Not quite your First Love, but better than your Heartbreak – the Rebound person/job is a peculiar thing.

We know the person/job isn’t forever, we’re only biding time until that “something better” comes along. We’ll most likely think about the good times from our First Love and what went wrong with our Heartbreak. We vow to never make the same mistakes.

Hopefully, no matter how long it lasts – we’re still learning from the experience and gaining more valuable knowledge.

True Love

If you’ve made it this far, I’ll take a stab and say most are agreeing with the similarities. But True Love is the summit not all of us have reached yet – I know I haven’t. We maintain the belief that after all these ups and downs, “the one” is out there waiting for us. It could be that we already have “the one” and don’t know it.

What makes this stage so special is we regain those feelings from our First Love, but at a much deeper level. The reality from Heartbreak helped us grow beyond superficial interests.

This stage could be described by piecing together the best parts of the earlier stages: First Love, Heartbreak, & Rebound. Each step provided us with a necessary experience, and we take the information gathered along the way to help us grow. We end up learning more about ourselves in the process, and eventually find exactly what we’re looking for.

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