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Your dream job is waiting for you to invent it

The career that would make you happiest probably doesn’t exist - yet.

Phil Rosen's avatar
Phil Rosen
Nov 13, 2023

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Work on its own won’t guarantee a meaningful life, but spending your time on something that feels productive, gratifying, and interesting seems to be a critical part of the equation. 

It also seems true that, over time, working at something you dislike would push you further from happiness. 

That said, I know many people who do not enjoy their jobs. It’s an exchange of time for money, they tell me, not some vehicle for purpose. Some of these friends earn very high salaries.

I also know people who make less money, but nonetheless appear happier than the former group because they found a way to do something they love. Then again, some have found a way to do what they love and make it lucrative.

Two types of careers

Broadly, everyone I know falls into two types of careers.

For the first type, when a company has an open position, recruiters scour LinkedIn for suitable candidates or they parse through stacks of applications. Plenty of these jobs pay well, and the corporate ladder is effectively inexhaustible.

Here it's usually the case that the more jobs you have under your belt, the higher-paying the role you can apply for next. 

The second path, however, doesn’t show up on job boards. Recruiters don’t talk about it because they don't know about it. The opportunity doesn’t actually exist — until you invent it. 

I concede that there’s no such thing as a perfect job, but for today’s purposes let’s call this option your dream job. Thanks to the internet, the world has never been filled with more possibilities to forge your own path.

Inventing your dream job looks something like this: 

  1. Do a lot of work on something you’re interested in

  2. Do so much of it that the skills involved become your unfair advantage

  3. You end up building a reputation for that unfair advantage

  4. Your unfair advantage meets opportunity 

    • You recognize where you could apply your skills and advantage (you find your market)

    • Someone else recognizes where you could apply your skills and advantage (the market or a player in the market finds you)

This formula works for landing an existing job you want or inventing something new.

That new opportunity, in turn, could be either at an existing company or something via entrepreneurship, like founding a brand or launching a product or service. 

This framework fits particularly well for writers, but it applies to other remote-first skills like design, website building, programming, and a number of other pursuits I probably haven't even heard of.

Side projects can catalyze a career

I always wanted to be a writer, but when I graduated college with a science degree, I had no experience in writing.

I wasn’t yet qualified for any jobs I wanted, so I got a job as an English teacher in Hong Kong for the purpose of making time to write during my evenings. I published articles every week on my website and on Medium, and committed to writing the type of writing I'd ideally love to get paid to do.

I barely had any readers, but six months later, I used a portfolio of roughly 50 essays to get a job at a newspaper overseas. The hiring manager opened the role specifically for me, and it didn’t exist until I was on his radar. 

The same thing happened when I leveraged my blog to earn academic scholarships, fellowships, and job offers at global media outlets.

Luck follows ambition

Individuals who fall into the “dream job” camp nearly always have ambition and luck. 

When someone who is curious and diligent enough to do something for long enough that they become highly competent (ambition), they often also chance upon people who are in search of those particular skills (luck). 

To be sure, luck in this scenario is not about the universe or what’s written in the stars. It’s a consequence of showing up over and over until A) you realize who could benefit from the work you’ve already put in, or B) someone else notices the work you’ve already put in.  

Drive and persistence are prerequisites for A or B. It’s unlikely that a person who’s invented their dream job would have become lucky, per se, if they hadn’t first worked extremely hard. 

While the dream-job scenario is less common, I don’t believe the likelihood of success is much different than applying for more conventional roles. 

An existing job posting for a product manager role at Google, for example, can attract thousands of applicants per day. If you're a compelling enough applicant to feel confident with those odds, you might as well try your hand at your own thing instead.

Inventing your dream job requires initiative, but every single day new free platforms and tools go online that help people do great independent work.

Plus, there are an increasing number of people who aren't sure what type of person they need to solve their problems. They know only that they want to pay top dollar for someone with specific skills and gumption.

With a little luck, that could be you.


I write about powerful ideas, recession-proof skills, and building a personal brand in my newsletter every week. Join 1,850+ subscribers here.


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