Finding Your Passion: Date Your Career Before You Marry It

Too many people jump into careers they think they will be happy with. They take out student loans, invest years in grad school, and study for hundreds of hours accumulating certifications they’ll never use. Now they’re too deep into debt and too many years into their career to make a change.

It doesn’t have to be like this.

Our Broken Education System

You see our education system is antiquated. Designed for an era where factory and farm work was the norm, it was designed to teach us how to function in these environments;

  • Showing up early and on time.
  • Sitting still.
  • Paying attention to instructions.
  • Being quiet
  • Changing stations when the buzzer goes off.

These are skills that make a great factory employee, but not the skills needed to blossom in the information age we live in where creativity and action are rewarded.

Despite this obvious misalignment in training, we still trust this system with finding our passion. We think being good in science class means you will make an excellent doctor, or being good at math means you should be an accountant. Deep down, you sensed this was wrong. It’s why you changed majors in college several times. It’s why you’re still unsure about your career after graduating. It’s why, when you finally started your first job, things were much different than you expected. In fact, you learned almost every skill “on the job”. Wasn’t school suppose to be prepare you for the real world?

Were all those classes a waste?

Did you pick the wrong career?

Maybe grad school will help you find a better job?

But what is a better job? Do you even know what that is? How can you be sure it’s not another dead end like your existing position?

Christina graduated from school in Australia and decided to become an architect. She excelled in school and upon graduating got an excellent job in a competitive industry. After two years she realized things were much different than we she had imagined. She no longer wanted to be an architect. She quit and is now pursuing her real passion.

So how do we supercharge this learning and fix this problem? How can we learn what Christina learned earlier in our career without investing years of school and thousands of dollars in debt?

Fake Internships

You already know that jobs are different than their sister subjects in school. This is why school is such a poor predictor of career happiness. The only way you can truly know if you will enjoy a job is by actually doing the job. But how?

A PDF that I discovered early on my college career that changed my life was Charlie Hoehn‘s Recession Proof Graduate. He advocates doing free work to land your dream job. It’s a revolutionary body of work that changed my life.

But what if you don’t know what your dream job is? Or what if your “dream job” actually turns out to be worse than your current job?

You have to create fake internships.

We already know that the majority of jobs are not filled by job postings and are usually manufactured, created, and filled by your network. So why not use your network to help you learn more about a potential career path? Are you interested in law? Email your lawyer friend. Advertising? Your friend at an advertising firm. Technology start-up? You get the idea.

Simply shoot them an email asking if you can shadow them for a day for a school project (BrokerChange University :p) and want to find out more about a typical day in their life. When you arrive, show up dressed to impress, bring copies of your resume, and be ready and willing to help out where possible.



Kissing Couple
You’ve just manufactured a fake internship


Now you’re no longer guessing what a career is like, you’re actually living it. You’re sitting in meetings, answering emails, creating decks, and living the day in the life. If you do this well enough, you may even get offered to stick around for an actual internship.

Protip: Don’t forget you can also do this at your existing job.

“All too often we fall into a head down work mode, and forget to tell our coworkers what we’d really like to be doing, and more importantly how we think our skills and interests can benefit the company.” — Sean Ogle

Finding “The One”

Yes this requires work. Yes this will require sacrificed mornings and weekends.

But it beats the alternative — getting into an arranged marriage with a career you’re not happy with. You read 100 reviews on Amazon before buying your last toaster, shouldn’t your career deserve the same level of research?

Going on multiple dates — *ahem* internships — is the only way you will find “the one”.

Jennifer Turliuk did this after being unhappy in her corporate gig. Like most of you she spent “more thought and effort into getting the job than into figuring out if it was something [she] actually wanted.” So she entered a competition to shadow Dave McClure of 500 startup fame, cold emailed a bunch of startups, and spent enough time in the community to know this was her true calling. She quit her job, moved to San Fran, and started her own startup knowing full well she was ready to put a ring on it.

Until you do the same you will never know what truly excites you. If you’re not reading articles, attending conferences, working overtime, and getting excited for Mondays, you haven’t found your calling yet. You need to keep dating. You gotta kiss more frogs before you find your prince.

Don’t be like Alex.

Date your career before you marry it. (Tweet This)

Your Homework

My challenge to you.

Try this 5 times.

Don’t get married to one idea. Don’t get “one-itis” with your first fake internship. In fact, your goal should be 30 “jobs” by the time you hit 30. Commit to trying several different industries and companies. Once you’re certain you’ve found the one – commit to becoming an expert. Black belts are 100x more impressive than brown belts. 

Still stuck? Steal my email “swipe file” with a huge list of response optimized emails you can copy/paste depending on your situation (cold email, warm email, etc). You can download them for free below.

P.S. I’m currently on a last minute vacation in Phuket so my previously scheduled post on picking your first business idea will hit your inbox shortly. See you then.

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