Making It Happen

Moving to Cayman | Happily in Pursuit

Since sharing the news of our big move and the creation of this site, I’ve received so many amazing messages and notes of support, but also a lot of questions.

  • How did you do this?
  • Why Cayman?
  • What will you be doing there?
  • And my fave: Are you just looking to live a more slow-paced, island life?

I’ve loved responding to these and thought I’d share all the answers in one place:

Moving to Cayman | Happily in Pursuit

The Why

For nearly a year, I explored the Toronto job market to see if there were any new challenges that caught my interest. After a couple dozen applications and several exhausting interviews (a few of which I actually decided to withdraw my application afterwards), I was overwhelmingly frustrated that I couldn’t find anything to get excited about. After leaving his startup last year, Ben was feeling the same way.

I wanted that small-team feel, a product I could be passionate about, and future growth opportunities. I also craved the cutting-edge; I was constantly researching new marketing systems and platforms and wanted to join a marketing team that valued staying on top of these trends.

Ben and I also have a desire to, at some point, live in a small town outside the city, like Creemore, Collingwood, or Trent Hills – anywhere with lots of outdoor space! Every time we visited Ben’s parents, who live and work in Grand Cayman, we would talk about what life would be like if we lived there, too: after-work beers in the sand watching the sunset, early morning runs before the heat set in, and generally slowing things down a bit. It would be our segue into small-town living but with year-round sunshine.

Hammock on beach in Little Cayman
The How

When we were visiting Cayman in December, Ben was presented with an amazing opportunity to take on a new operations initiative with an engineering firm. With that in mind, I started job hunting. Silly me, I went to the “traditional” job hunting websites, poring over sites like LinkedIn and Glassdoor. It didn’t take me long to discover that, unless I had a background in accounting or insurance, I was not going to find a job in Cayman on those platforms. 

I began researching companies to apply to directly as well as reading the classifieds in the local paper online. The sometimes frustrating thing about job postings in Cayman is that they’re not actually available – it’s a posting required to renew the current job-holder’s work permit. So, after a couple direct applications that didn’t go anywhere, I reached out to on-island recruitment agencies and heard back from Stepping Stones. They asked to arrange a call and within just a few weeks had sent me 3 or 4 exciting job descriptions. But the best part was when I interviewed for a position with a growing financial content-creation startup. The first role wasn’t a fit, but they said they loved me and offered me a new role as Marketing Account Executive the day after my second interview! 

And Nino?Happily in Pursuit Nino Himalayan Cat

Nino is our cat and we wouldn’t dream of leaving him behind! Cayman is a rabies-free island so there is a wait period to import him after some blood tests and immunizations, but our lovable, furry grouch will be joining us in mid-May. From the streets of Toronto, to the beaches of Grand Cayman, this cat sure hit the jackpot!

Happily in Pursuit | Cayman Lifestyle Blog

And finally…

I think the majority of these questions have come from people who’ve said they would love to do the exact same thing as us. I so want to stress that the only thing stopping you is you! If you really want to move to another country, you can make it happen. I often think where I’d be if I’d let those first few no-response job applications bum me out, or if I’d given up when the first two recruitment agencies refused to interview me because “marketing jobs rarely become available,” or even when I didn’t get that first role at my new company. (“In Toronto” I guess would be the answer to that one…)

My final advice would be to keep searching, be patient, but also be prepared to make a very quick decision that could change your whole life. I was completely caught off guard when my job offer came in so quickly, but because we’d planned and made some pro/con lists, we felt solid in our decision within just a few days. At the end of the day, how often does an opportunity like this come along? We decided to grab it and run with it, and have yet to look back.

P.S. If you’re also specifically interested in life in Grand Cayman, the absolute best resource is Cayman Resident – check it out!


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  1. Great read, Devlin. I think the main take away is not to give up. Set your sights on something and then work towards that. It doesn’t matter how many times the universe tells you it’s unrealistic or unreasonable. If you want something bad enough and keeping taking those incremental steps towards it , then it will happen.

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