How a dream job is like a dream relationship

There’s a helluva difference between the idea of a romantic relationship and the reality of it, and there’s a helluva difference between the idea of your dream job, career, business and the reality of achieving/living it.

They go through similar stages.

The dream relationship overview

At the beginning of a romantic relationship we dream about “the one,” and the excitement about the possibility. Then there’s the excitement at the meeting of the candidate, the ogling, the flirting, then the passion of the first weeks or months or—if you’re lucky—years of the relationship.

Then at some point there comes disillusionment, when the things you don’t like about her/him become very plain, and there’s being with the effect of him/her realizing similar things about you.

This period is characterized by the inevitable communication breakdowns and even the forgetting of what it was you were creating with the relationship in the first place.

If not handled effectively—which also means in a timely fashion—you soon find yourself saying, “What was I thinking?” and “What did I see in this person in the first place?”

At this point one of the following three things occur: (1) the reinvention of the relationship—made possible by authentic communication (2) the conscious or unconscious choice to stay in the uninspired relationship, or (3) the dissolution of the relationship.

I think the same think can happen for your dream job, business or career. Let’s look at the specific stages a dream relationship goes through and compare it with the stages your dream job or business goes through.

The dream

For the dream relationship women dream about what he would look like, the great job he would have, the home they would share, the kids they would raise, places they would go, how they would support each other etc., etc.

You already know what men think about.

For the dream job you think of what you want out of it, what it would provide you, and ideally how it would really make a difference in the world.

In this dream stage there’s no actual person and as yet—for the job/business—no real idea of what could make that dream come true.

At this point it’s all fantasy.

At this stage no one thinks about the mundanity, the irritations and exasperations of living with another person and all the baggage they bring and the baggage that you both will produce.

For the dream job, no one can even imagine that their dream job may carry much of the same frustrations, disappointments, setbacks, politics and conflicts that they they think they are leaving behind.

The first meeting and the idea

Then one day there’s the meeting of the person or the birth of the business idea.

Excitement about possibility flows like electricity.

The flirting

In the relationship this excitement then lives in the flirting: the dance with seduction and possibility.

The reciprocation from your intended target fans the flame and through the flirting the dream lives as an immediate opportunity.

This is exactly the same with the business or career idea. In your mind you ask the idea questions about it’s possibility to work for you and it responds favorably. Yes, you think, this idea likes me.

It could happen.

The seduction (or not)

Now it’s all about getting into bed with this person or idea. Might not be an analogy you like, but people use it a lot when they talk about business relationships.

Getting into bed is a necessary, but not sufficient condition to move forward; meaning it may not mean anything even when it happens, but if it doesn’t happen it certainly won’t fulfill your dream.

So the flirting must lead to the consummation of the relationship if it is to proceed to the fulfillment of that dream, and here is where it breaks down for most people.

Some people are good at closing the deal—they are the serial closers and are the world’s pick-up artists and business deal makers—and some don’t.

They leave it to chance that they will see the girl/idea again, and when they do they never take it past the flirt; they don’t up the ante, they procrastinate and then the flame dies out.

And here the parallel between the business idea and the girl/guy is clear.

In the case of the girl of your dreams you don’t think she’d really be interested in you and you don’t pursue her; only to find out years later that she would have jumped your bones if you only had the courage to approach.

(Sadly—or tragically—autobiographical.  Buy me a drink and I’ll tell you all about them.)

For many people this is indeed the tragic story of actually doing the work they love. They have the idea of what it could be, they flirt with the idea every now and then, but they never approach, they never even try because they don’t think it’s possible for them, when in fact the only thing in their way is their own belief that it’s not possible.


Immediately after the seduction, reality sets in, the relationship is now real and there is something about this stage that excites some people, and scares the beJesus out of others.

In human relationships women will recognize the men that disappear immediately after the seduction.

Reason is, that unlike the exciting flirting and seduction where you live for the one possibility, the post-seduction stage is defined by the things you now “have” to do, and the things you can no longer do—commitment; the anti-aphrodesiac, the place where boners go to die.

Lucky for society, there are those who become present to a new excitement, different from the flirting/pre-seduction excitement; the excitement of building something together with someone else.

For the dream job, or entrepreneurial idea that will set you free, a similar thing happens.

Once you get past the dreamy flirtations with the idea and form the company, the reality of the work that needs to be done sets in.

This new business idea now has expectations and demands to be met. The business or job brings with it commitments and keeping commitments means work and loss of freedom. No wonder the thrill is gone.

So, what’s

the moral of the story?

That it can’t all be fun, laughter, excitement and play.

There is no fairy tale of happily ever after.

It’s just the nature of life that every great, fun, exciting activity produces unwanted by-product (aka shit) that you must deal with.

Puppies do it, and dream jobs/relationships are no different.

That you have to practice reminding yourself of what you have and what you’re creating. And that even when it’s not hot and steamy, you’re still in the relationship of your dream; you’re still creating and living the work that you love.

Just like when I used to live on the 44th floor with a view of Manhattan that took your breath away. Within a few short months I stopped noticing the view, and living in that fabulous apartment was no longer special. It was only when people visited for the first time that I appreciated my good fortune; when they gasped at the view of the Empire State and the Chrysler building that I remembered to look anew at the views out of my windows.

I had to remind myself of what I had.


Having work that you love, is just like having the relationship of your dreams; it’s not always romantic, sexy and funny. There are rocky periods and days when you want to kill her/him, and days when you want to quit. But with a good practice to remember and appreciate what you have and what you are creating, you wouldn’t choose anyone/anything else.

This is what it means to be alive, to go through dips and valleys and have to remind yourself that your current dip is much higher than the peaks you left behind.

Any thoughts? Contributions/acknowledgments welcome.