How Can I Land My Dream Job?

Escape the City celebrated their 5th birthday this week.

We celebrated by surprising Escape co-founders Rob, Dom & Mikey with an “Esc Key” cake (thanks Mel) and an epic print (thanks Tessa) that reads:


I say we, because somehow, someway, I became a part of that tribe just over a year ago.

As I sit at a desk in the Escape office, tucked away in a previously vacant office space in a corner of The City of London, it feels surreal to wonder:

How did I end up here in London?

How did I become part of this team?

How in the world am I working with a group of guys I once, and still do admire?

How am I spending days (and nights) working on such an ambitious and daunting mission as this:

How did I go from a job that I drifted into, to one that I more deliberately marched towards; one that challenges me to grow, rewards me for being me, is packed with meaning and fulfilment, and helps me to help others pursue the same?

How did I “get” a job with Escape the City? Not just any job, but one so well aligned to my values, strengths, gifts, my personal mission and ideal way of working?

More broadly, how does one find work that matters to them? How does one find a job they’ll love?

Better still, how does one land their own dream job?

Dream Jobs and Soul Mates.

Let me first caveat this whole essay by saying I have a hard time using the phrase “dream job” without stuttering and choking on my words. Much like the reality that there’s likely not one single human predestined to be your sole soulmate and your role here on Earth is to search through a sea of billions to find the face that’s your other half.

(I’m going on a date tonight so please check back with me tomorrow in case the universe, who loves to prove me wrong, proves me wrong.)

My aversion to the phrase dream job could be because I’m a “classic Seven” as we’d say here at Escape. Seven being my Enneagram personality style and Enneagram being based on the premise that “each of us have one dominant (not exclusive) energy that drives us in everything we do.” I know I’m a classic Seven because a guy named Clarence in Kansas told me so after I answered a series of questions like “How would you spend a full free day that you had no obligations?”[1] and “If you were an animal, what kind would you be?”[2].

(My answers: [1] Wandering around and exploring a new place; [2] An eagle.)

Maybe I have a hard time committing to the idea that there’s a neatly packaged “dream job” waiting for us, because, as the Peter Pan or “eternal youth” of the personality types, I’m told I fear boxes, boredom, confinement and committing to one thing for the daunting-ness of forever. (Spoiler-alert tonight’s and all future nights’ dates!). Instead, I subscribe to the idea that maybe there’s potential for multiple soul mates, and similarly, multiple dream jobs.

But the simple truth is that we instantly get on well with some people, while others rub us the wrong way. Similarly, there are just certain jobs, lines of work and companies that feel right. And others that don’t.

How do you separate the wheat from the chaff? How do you go about finding those soulmate-like jobs?

Like every other Essay, I can only write about what I know. And all I know is how I got a job with Escape the City. So if you’ll bear with me, it’s a quick one — it only took four and a half years.

Connecting the Dots, Backwards.

Steve Jobs’s quote has become quite the cliched phrase. But the thing about cliches is that they’re usually packed with truth.

“You can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.” –Steve Jobs

I found this to be true in travel. And I find it to be true in work. Taking a page from 37Signals co-founder Jason Fried’s Connecting the dots: How my opinion made it into the New York Times today, here are the dots that connected me to Escape — what could be described today as a dream job.

November 8, 2014

I boarded a flight to London holding a freshly-minted Visa to live and work in the UK. Escape the City (specifically co-founders Rob, Dom and Mikey) fought to bring me into the country to work beside them to execute and grow The Escape School.


June 11, 2014

Because I had just spent the past three months, at the sweet talking of co-founder Rob, spending my blood, sweat and tears to launch a crazy project called The Escape School. It wasn’t just about talks, events, courses and workshops — we had launched a physical space 500 feet from the Bank of England to craft unique experiences for Escape members; experiences that just may encourage and empower a person to quit their unfulfilling jobs.

With the rest of the Escape team, we bootstrapped our way to create a safe haven for Londoners to gather and help each other pursue work and a life that matters (often under incredible uncertainty and a constant feeling of shit, this might not work!). 


January 5, 2013

Because Adele, Escape’s first official employee and a close friend of mine, asked if I would come to London and help her run events and courses for Escape at the beginning of 2014, and ideally, reignite Escape’s education arm to become a real tour de force.


September 23, 2013

Because I had taught myself the ins and outs of self-publishing from launching Tales of Iceland, Adele asked if I’d help her publish an Escape guide, How to Escape the MBA Debate. Through this project, we figured out we worked well together and really enjoyed working on stuff side-by-side. We’d also developed a level of trust so pertinent in any sort of shared undertaking.


July 3, 2013

Because Adele and I had gotten to know each other from my previous trips through London. Each time I came through, she convinced me to do something with Escape. One of those times, she asked me to speak to the Escape community on a talk entitled “How to Escape and Build a Life Travelling the World” (even though I was pretty sure I didn’t yet have the chops to command a crowd). She saw something in me I didn’t quite see in myself yet.


January 22, 2013

Because Adele had seen how well a blog post I’d written for Escape had been received by the founders and the community. In it, I shared the nuts and bolts of how I negotiated a seven-month sabbatical from my employer. I wanted to help more people “escape,” if that’s something they wanted to do. I wanted to further my own writing, and at the same time, help perpetuate Escape’s mission.


October 16, 2012

Because I respected the guys who started Escape, but more importantly, I personally subscribed to their mission. It was tightly aligned with my own mission. This became quite obvious when I found out that Rob, one of Escape’s co-founders, had subscribed to, was sharing, and was commenting on my own blog It seemed that we were developing a mutual respect for one another.


July 22, 2012

Because I decided to pass through London on my 7-month deliberate wandering, specifically to meet the Escape team. They agreed to let me join them for lunch, and when I did, felt an instant connection with Adele, Rob and the team.


April 14, 2012

Because one day I decided to fill out a survey for Escape the City — some website and newsletter I had recently subscribed to. I instantly forgot that I filled it out, but months later when Adele joined as Escape’s Community Manager and read through the comments — mine stuck out to her. She reached out for my opinion, and in doing so, created a fan for life.

I believed in Escape’s mission to help people do work that matters. Enough so that I spent some time carefully answering their survey.


June 10, 2011

Because I had subscribed to Escape the City’s newsletter after my buddy Mike shared an article about them in our Chicago Business Book Club facebook group. Their story resonated. Specifically their video.


October 9, 2010

Because my flatmates Mike, Brian and I had started a book club together.


Because we felt a certain inexplicable void. Because we couldn’t find meaning and fulfilment in our jobs and we wondered why that was. Because we didn’t know of a forum where we could discuss these complex topics and questions of work and life. Because we knew we didn’t have the answers to such complex questions, but we still cared enough to figure out why that was.

The Moral of the Story.

While the moral of the story isn’t necessarily to start a book club with your flatmate, it is of a similar flavour.

You don’t get closer to a dream job by wishing and hoping, by perusing job boards (ironic given that’s part of our business), or by machine-gun firing off your resume to any company with a pulse.

You land a dream job by doing things that matter to you. Through action. By leaving the building and getting to know people who care about the same things you care about.

The more logical of you are thinking what specifically can I do?  In honour of Clarence from Kansas, here are Seven thoughts:

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 partner, 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 whoever 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 taught to operate 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 & co. 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.

(Related: Ramit Sethi’s Briefcase Technique).

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 — and 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.

This is an excerpt from a 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 Your Dream Job 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 realising 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.

7. Have a Mission.

Why is Escape the City 5 years old today?

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 the reason most don’t bother. Most can’t stomach the long-game. It’s a marathon. It goes against the instant gratification we’ve learned 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, traveller, 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 here 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 a 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.

Doing something different with your life and career is hard… but you don’t have to do it alone. If you need help with your Escape, check out our Tribe programmes.

Share This