London-based startup Escape the City celebrated their 5th birthday earlier this year. We celebrated by surprising Escape co-founders Rob, Dom & Mikey with an “Esc Key” cake and an epic print 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 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 fulfillment, 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 post 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.

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. 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 post, 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, 2014

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 Traveling 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 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 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 fulfillment 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 flavor.

I don’t believe you get closer to a dream job by wishing and hoping, by perusing job boards (ironic given that’s part of Escape’s 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.

At least that’s what seemed to work for me.

(In the next post, I’ll share some tangible tips for getting your foot in the door with a new opportunity — things that have worked for me and for people I meet at Escape events: Seven Ideas for Getting Closer to a Dream Job).

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