In How to Land Your Dream Job, I detailed the long and winding road that led me to working with Escape in London. Hopefully my story sparked some ideas for you if you’re transitioning or hope to be transitioning in the near future. But what if you don’t have a clue what your dream job looks like? What if you feel stuck and you don’t know where to start?

In this post, I’d like to offer some suggestions on ways to get closer to a dream job, even if you can’t fully articulate what that dream job is yet; things I’ve stumbled upon through my own transition, or things that seem to work for people I meet at Escape.

In honor of my “Seven” enneagram style, here are seven ideas for getting closer to your dream job:

1. Learn How to Date Supermodels

How would you woo a mate? Would you apply for a position? Would you polish your LinkedIn page, write up a cover letter, and blast it off to anyone who’s looking (or not)? I guess you could, but based on my experience, nothing good will come from that.

Rob Fitzpatrick, co-founder at Founder Centric and our startup education parter at Escape, has a great anecdote for the “How Do I Find a Co-Founder?” question. He paraphrases advice he heard from a friend of a friend, an average looking bloke, who is somehow always dating supermodels:

“You take your laptop and go work out of cafes across the street from a photography studio or agency where supermodels work. You need to be where they are and then say hello to them sometimes. That’s pretty much it.”

The same seems to apply to whatever company, person or industry you’d like to “date.” Go to where the “supermodels” are. For me, that meant actually going to London, purposefully, to meet a team I respected.

2. Adopt a Supplier Mindset (vs. a Customer Mindset)


Adele often talks about the importance of adopting a supplier mindset when looking for jobs. Which goes against the customer mindset we’ve been mostly operating by:

  • To your parents: “I’m a child — give me food and shelter and other things I need.”
  • To your school and university: “I’m a student — give me the education I require.”

Yet when we get to jobs, this no longer works. At least not with most work that matters. Instead, we should adopt a supplier mindset — one that stresses and expresses what value you can give. Not the things you can take.

For me, I tried proving my value through action. Adele &  had seen me in action already. I didn’t have to convince them of my worth and my value. I demonstrated it clearly — through my personal blog and my achievements in publishing. Eventually, Escape had a use for the types of things I could supply.

On a related note, check out Ramit Sethi’s Briefcase Technique for a top tip on job interviews — which involves instantly showing value in the interview (vs. just talking about it, like we usually do).

3. Do Free Work

In my journey toward Escape, I did many things for free. Not just for the sake of it, but because I cared about the mission and wanted to add value and push it forward. This manifested as a survey, a blog post, a talk, and at times doing work that had no guarantee of a return (e.g. running with the Escape School).

Stupid? Perhaps. But looking at the long game, a different story emerges.

Charlie Hoehn, author of The Recession-Proof Graduate and previously Tim Ferriss’s right hand man, has an excellent TEDx talk on the value of free work:

4. Follow Your Tennis Ball(s)


This is my antidote to the “Find Your Passion” myth. Stolen from Drew Houston, founder of Dropbox, who states in his MIT commencement speech:

“When I think about it, the happiest and most successful people I know don’t just love what they do, they’re obsessed with solving an important problem, something that matters to them. They remind me of a dog chasing a tennis ball: their eyes go a little crazy, the leash snaps and they go bounding off, plowing through whatever gets in the way…

…it’s not about pushing yourself; it’s about finding your tennis ball, the thing that pulls you. It might take a while, but until you find it, keep listening for that little voice.”

That little voice told me to go to London to visit Escape. I had no clue how it would turn out, but I couldn’t deny that I heard the voice, and I gave myself permission to listen to it.

5. Be a Hustler

This is a whole topic in and of itself — an essay for another day. So I’ll leave you with two things that I think hit upon what I mean by be a hustler.

First, this image:

Joey Roth:

And second, this blog post by Seth Godin:

“…there’s the hustle that’s actually quite difficult and effective. This is the hustle of being more generous than you need to be, of speaking truthfully even if it delays the ultimate goal in the short run, and most of all, the hustle of being prepared and of doing the work.”

6. Know What You Want (and What It Feels Like)

We seem to have forgotten that the primary purpose of a job is to serve the lifestyle we want to live; not the other way around.

To me, a dream job is one in which I can work beside people who inspire me and whom I respect. It’s working on projects that matter to me, and ideally, to the world. It’s about realizing the ideal that work has the potential to be “love made visible.” It’s being part of a mission that’s bigger than just myself; ideally a mission that’s tightly aligned to my own personal mission.

What does your dream job feel like? Write it down. Clearly articulate it.

(This is similar to something Amber Rae calls the “Ideal Day Manifesto” — an articulation of not just your job, but of your life, as embodied in a single day. What does your ideal day look, sound, taste, feel like? Write it down.)

7. Have a Mission

Why is Escape the City 5 years old this year?

Because the founders were too stubborn to quit, even when the going was tough.

Why is that? I can’t speak entirely for them, but after working beside them for a bit, I have a hunch:

It’s probably because their personal mission is so tightly tied to the mission of Escape — a mission they cared deeply about — that even as they went up and down on the roller coaster ride that is a startup, their shared mission kept them hanging on tight.

When you have a mission and your work is conjoined to that mission like a siamese twin, you and your dream job have a better shot at finding each other. When mission and meaning is embedded in what you do, it doesn’t matter how many countless people and companies don’t get it; all that matters are the ones who do. You’d be smart to find those and get closer to them.

“Imagine that you are 45 and are looking back on your last 15-20 years. Is your work, and life, full of meaning?” —Brad Feld, A Message to Graduating MBAs

279 Days to Overnight Success

If people knew how long it takes to begin again in their career, most wouldn’t bother. Maybe that’s why most don’t bother. Most can’t stomach the long-game. It’s a marathon. It goes against the instant gratification we’ve learn to accept as truth. A swipe, a like, a click, a buy-it-now button — and we instantly receive what we want.

In the world of things that matter, that’s not always the case.

Maybe that’s why we don’t start. Because we’re aware how long it’s going to take. We know deep down how difficult it will be, how uncertain the path, how ugly and awkward it is to start (or re-start).

279 Days to Overnight Success is the title of an ebook by author, traveler, entrepreneur Chris Guillebeau. It’s a manifesto that details how he started a successful blog and what it took to get there (available for free here).

I don’t use that phrase to show you that I’ve reached a success by being at Escape (although I am proud to be here). In fact, it took me much longer than 279 days to get here. I just love this turn of phrase because the irony of it smacks you in the face like a wet fish: there’s nothing more ridiculous than the concept of an overnight success.

Just as there’s nothing more ridiculous than finding your dream job overnight.

But if you care enough to find your dream job (or if you’re an enneagram Seven like me, one of your dream jobs), if you’re ready for the long haul it may require, if you’re following your tennis balls, if you’re living your mission, if you’re hustling your socks off — the dots may be connecting as we speak.

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