How to Find Your Dream Job (And Soul Mate)

by Alexander Heyne · 22 comments


“I have this great job, with benefits, tons of money, freedom, and great hours… so why am I not happy?”

Someone recently asked me this question, and I realized that many people have asked me this question over the years. It is pretty perplexing after all – logically, it looks great on paper.

I have everything I’m supposed to want. Everything I should want, so why am I not happy?


The other day my friend shot me a text after going on a date with a new girl he had just met for the first time.

He had met her once before for just a few minutes, and told me how interested he was in this girl.

“Dude this girl is an awesome conversationalist, she has cool hobbies, she’s into yoga, she also does PR for work, she loves travel, and is crazy exciting. Oh… and she’s blazin.”

My friend was obviously pretty excited about meeting this girl and getting her number, so I asked him how the date went a few weeks later.

“Dude. Flatlined.”

Me: “What?!”

“She looked great on paper – if I had a checklist, she had it all. But when we went out to dinner and hung out after, there was absolutely no spark, no connection. It was the weirdest thing. I felt like I should be attracted to her because it was all there, but I wasn’t. What the hell man.”


Finding your dream job is a lot like finding your dream partner.

No matter how much he/she looks great on paper, it just won’t work unless it intuitively feels right and just works.

Just like my friend who met up with this girl who seemed perfect on paper, when he met her in person and hung out for a while, it was intuitively obvious that it wouldn’t work and he wasn’t into her.

Checklists, criteria, and standards – Oh my !

How many of you have these long checklists of standards, criteria, and qualities you want in a job or a mate?

Are they important? Yeah!

But should you base your search entirely on them? My opinion is no. Actually, hell no. Here’s why.

Intuition is one of the most powerful forces in your life. A lot more powerful than intellect.  If you ask me, intuition is nothing mystical – it’s just the brain sped up, processing many times faster than usual. It’s a snap decision, made with all the information at hand, before you can even process it. You feel it in your gut.

In fact, an entire book has been written on the subject by a lead police detective, called The Gift of Fear (highly recommended).

The entire book was based on one fact: Almost all of the people that are victims of crime had some kind of intuition about it before the event happened – the ones that ignored it were injured, raped, or murdered. The ones that listened to it survived unharmed.

From a less gruesome perspective, many of the best and brightest business minds talk about the importance of intuition over intellect.  And, well, since the entire start up world has a hard on for Steve Jobs, I’ll use him as an example:

This is from his biography:

“Coming back to America was, for me, much more of a cultural shock than going to India. The people in the Indian countryside don’t use their intellect like we do, they use their intuition instead, and their intuition is far more developed than in the rest of the world.

Intuition is a very powerful thing, more powerful than intellect, in my opinion. That’s had a big impact on my work.  Western rational thought is not an innate human characteristic, it is learned and is the great achievement of Western civilization. In the villages of India, they never learned it. They learned something else, which is in some ways just as valuable but in other ways is not. That’s the power of intuition and experiential wisdom.

Coming back after seven months in Indian villages, I saw the craziness of the Western world as well as its capacity for rational thought.” (emphasis mine)

Intuition and intellect have their own places in life.

The problem, as I see it, is that people spend too much time intellectualizing in the West and not enough time intuitively feeling what’s right. Decision making often becomes easy when you intuitively approach life.

Particularly with impossible decisions, people email me stuck and confused.

Do I stay or go?

Move across the country with my boyfriend/girlfriend?

Quit my job to start a business… even though I have no experience?

Drop it all to become a monk in Japan?

The problem with intellect is that you could make pro/con lists all day…. which is a real shitty way to make life decisions.

When your partner, your job, and your happiness and fulfillment in life are relegated to numbers or checks on a checklist… you’re doing something seriously wrong.

You’re doing it all wrong

I’m a huge fan of informal life talks with friends. In fact, If I had to list my #1 simple pleasure in life, it would be sitting down with people to a long dinner, plenty of wine, and just talking for hours about some kind of topic that is mutually interesting and has depth.

Naturally, someone ends up sharing some kind of story about a huge problem going on in their life, and we go back and forth about the pros/cons of each, weighing each side, and then the person ends up more confused than when we started.

Then I drop the bomb… “Intuitively, in 3 seconds, which path feels right? Even though it may be scary, unknown and uncharted? Even though, in the short run, it may make you miserable? Which path do you know you need to take?”

Without fail, people almost always immediately know the answer.

So how exactly do I go about finding my, uh “soul mate” and “dream job”

Alright, so how does this all relate to soul mates and dream jobs?

Let’s be honest, how in the hell do I “use” my intuition when there are 5,432 jobs showing up in a basic job search?

And how exactly do I go about finding someone I’m compatible with (if that hasn’t happened before)?

Here’s how:

  1. Narrow down the search via elimination
  2. Experiment… a lot
  3. Be patient

The path is really un-sexy, but it works better than anything I’ve found.

A. Narrow down the search.

Clearly you can’t just go down craigslist and be like “hmmmm, yes/no.”  That would take forever.

Instead, here’s what you do.

Remember this exercise? It’s basically a job search exercise from What Color is Your Parachute.

I talked about how to fill this thing out in the 5 most useful tools for figuring out your work in life.

Parachute the flower

This will help you narrow down the search.

Otherwise you have to potentially search through an uncountable numbers of jobs in business, finance, health, law, etc.

The first, most important step is elimination.

Eliminate things you definitely do not want, right now.

For example, I have zero-fucking-interest in doing anything related to law, anything related to being a NYC finance guy or banker, and anything related to accounting or statistics. That narrows my search a bit.

Then, B. you experiment.

Now, people seem to think that experimentation means “imagining what it would be like in your head.”

Uhhh, no that’s not experimentation.

Experimentation means getting some kind of job, temporary position, or physical daily experience in that potential job.

The amount of people that have emailed me about one of two career paths – without ever having tried either – is scary.

You will know very quickly whether or not you like something once you start doing it.

This is one of the biggest reasons I object to people going to grad school just for “shits and fuckin’ giggles.”  40k in student loans is shits and giggles? Potentially hating the job you get with that degree is shits and giggles?

A friend of mine recently moved to NYC looking to get into start-up life thinking it was the dream. The end. The goal.

… Except when he finally got a start-up job, he realized it sucked more than he could have ever imagined. It was boring, repetitive, un-glorious, and had lots of sales work.

Now imagine if he never tried it out, and just imagined being in a start-up versus, let’s say, joining the circus.

For months or years he would wonder which one he liked more, while potentially staying stuck in a job he hated, and never getting any answers. But all it would take is 30 days at a new job. Boom. Impossible question answered.

Another example:

I thought freelancing internet marketing for small business owners would be an awesome job. 1 on 1, a topic I know very well, and very meaningful if/when you help someone else succeed.

For months I considered quitting my job to do this thing full time, imaging how much fun I’d have and the freedom it’d give me (earning $75 an hour would mean I could work 1/3 or 1/4 or 1/5 the hours and still earn the same).

… And then I finally started doing it.

I got clients that bitched and moaned about everything. Clients that didn’t follow through. Clients that milked me and didn’t pay me.

… In other words, I didn’t know shit about freelancing. I had no idea about targeting a market, setting the bar high for my clients, and only dealing with ideal clients.

After three months, I was so drained by constantly looking for new clients, and dealing with the ones sapping my energy, that I never wanted to freelance again.  At least not the way I was doing it then.

Experimentation means DOING it… not thinking about it.

Fact: no matter how good or bad something seems in your head, those visions are all projections of reality and are not reality.

The most important part

What’s last? Patience.

People always tell you to chill out and enjoy the journey. The reason they say this, rather than being just a bunch of stoners, is that you can’t always control how fast the process happens.

This entire process of guess/test/refine takes time. And many of us go through 5, 10, 15+ jobs/relationships before finding one that works.

The key throughout it all? Use your intuition.

Otherwise one day you might wake up realizing you did all the stuff you should’ve done in life, without ever doing the stuff you wanted to do.

Thoughts, comments, douchebaggery, shenanigans? Hit me up below:

– Alex

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