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Career Lessons from Dating

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 I 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


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


.   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


– the


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


.  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


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.

Crystal's Questions:
What's your take on this?  What stage are you in with your career?

15 thoughts on “Career Lessons from Dating”

  1. everyday tips

    I haven’t really found my ‘career’ yet. I had a job for many years, but I only stuck with it because it was flexible. It was a paycheck, period.

    I would be so happy if I found something I loved. However, that is on hold until the kids are older.

    Good post!

  2. Rob

    Interesting perspective. I suppose I am at the “true love” stage as I am in the process of starting my own business and thoroughly enjoying it. It is still a work in process though…always will be it seems!

  3. BFS

    Everyday Tips, yep, I have a job but it is not my dream job. I’m still trying to figure out what my dream job is…well, other than blogging of course, lol. 🙂

  4. BFS

    Rob, good luck on your new business!!! Woot for the self-employed! Yep, there is always something to be done when you’re running something…but at least you have control. Congrats!

  5. Julie

    I guess I’m somewhere between rebound and true love. I have found the larger “company” I want to stay in forever, but I tend to get bored and apply for internal jobs a lot. I am constantly moving from one position to another adding new skills and enjoying myself.

  6. BFS

    Julie, I think it’s great that you’ve found a system that works for you. If they keep supporting it too by letting you move around, then you are set for life! Woot!

  7. FinEngr

    @ EveryDay Tips: Glad you enjoyed the post! You may not find something you love (yet), but you can definitely look for something that’s more than just a paycheck. Getting married shortly myself, the shift from individual to family unit does have large implications on pursuing that “dream” job. Good luck!

    @ Rob: Nice to hear! I think you’ve jumped enjoyed True Love into a stage I didn’t even think about – Utter Infatuation! If you love something so much that you’re willing to risk life & limb (professionally) by starting your own business, that says something about your relationship w/ that line of work. Good luck!

    @ Julie: This is a similar boat that I’m in. There’s millions of different tracks within a single industry, I’m fearful of closing myself off too early on. The big benefit with your situation is remaining within the company and transferring roles. Maybe it’s like Early True Love – where you know it’s true love, but you’re still new at it and have to figure out who will do the dishes. Eventually you should fall into something – Good Luck!

    @ BFS: Thanks for the chance to guest post and looking forward to more responses. Hope you had a great vacation in the islands! 🙂

  8. BFS

    No problem Fin Engr! Thanks for the great post!

  9. Financial Samurai

    At some point we all go past true love, and all go again towards first love over and over again as we constantly rediscover and re-invent ourselves!

  10. BFS

    Financial Samurai, I would just be happy to find true love, much less circle back to it. 🙂

  11. FinEngr

    @ Financial Samurai: Yes, we definitely realign our goals as we reach different levels of success. Once we achieve True Love, we can look within (our role in the company, side projects, etc) to find ways of igniting those same First Love feelings no?

  12. ODWO

    Hey there. My career relationship would have to be “on the Rebound” as it was the first thing to come along after the “heartbreak.” (closing a business partnership w/father)

    At this point in the career relationship, there’s a bit of (imo) soul searching going on. So, to quote song lyrics by the band The Clash, the question is … “Do I stay? or do I go?” is it time to move on and find a better paying job? Or stay with the proverbial bird in the hand?

    Interesting correlations!
    …. lurker in the shadows (aka: ODWO)

  13. FinEngr

    @ ODWO: Thanks for commenting. I especially enjoyed your thoughts as this is exactly the same situation I am currently in – almost identically. Yes, there’s a significant amount of soul searching that goes on after a blow like that (The Heartbreak).

    Maybe I’m naive, but I truly believe our True Love is out there and only ceases to exist once we decide to stop looking for it.

    Even though it’s a proverbial bird, you still have two real hands right? I’m trying to hold the bird in one and reach with the other. Best of Luck!

  14. ODWO

    @FinEngr – I agree. (my dilema) I’m just not sure if I’m the entrepreneurial type? (sp?) or the work for someone else type. I think (odd as this sounds) that my true love job is still out there. I tend to think it would/will be something that involves either a franchise type of business or something that involves lots of volumn (like a dry cleaners Biz’). Am I just impressed with the wealth they generate for others without seeing all the work involved or knowing how-to? There’s something to be said for watching (copycat) how others do it. The grass isn’t always greener somewhere else.

    My fear is just being tied to one source of income (working for someone else) while they get all the profits and I get a watch. Oh joy! 🙂

  15. FinEngr


    Thanks for the great comments & stopping by the site! 🙂

    If you’re looking at franchise or scalable, then I’d guess you are more the entrepreneurial type.

    Agree it’s amazing how much wealth some people generate with seemingly “easy” businesses, but I would bet all those individuals are very hard-working, driven, visionary, etc.

    Agree again. Only a select few can invent the “originals”, the rest of innovation comes through the refinement – making it better, faster, stronger, cheaper.

    haha – well best of luck not sitting on the bench watching!

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