From small-town bar tender to Caribbean shores

Being a digital nomad is something we hear about often in today’s business climate. Especially since the pandemic. It is now understood by the wider population that the workplace no longer needs to be confined to the four walls of a corporate office space.

Now more than ever young savvy entrepreneurs are seeking a lifestyle on their own clock. There are many diverse and interesting entry points to this way of life, and I am going to tell you the story about how I was able to make the break to global independence. From working in hospitality for years to crafting a more flexible existence. No time sheets, no schedule/Rota/roster, no micromanagement, no more smart casual dress code, no office politics!

These are things I have dreamed of since I entered the workforce at just 13, washing dishes at my local pub for 2.50 an hour. It has been a wildly windy journey consisting of all kinds of varied and interesting roles, but there have been some constants in my mindset:

  • Hard work pays off
  • Being on time (for meetings, or work) is easy
  • Creating lasting and meaningful relationships is key
  • Be great at leading people
  • Don’t shy away from real responsibility
  • Remove mental blockages (such as the need to stay in home town for other people)
  • I do not belong in anyone’s story apart from my own
  • Always do your absolute best every single day

People often ask me how I had the balls to make the break. What I tell them is that there is never a perfect moment, there is never a perfect amount of money, the only time we have, to make these choices is now. If it’s something you’ve always dreamed of, you have to ask yourself: “Are the barriers I’m up against real? Or are they excuses to stay in my comfort zone?” I understand that not all who dream it, are able to. Weather it’s family commitments or work-based issues, but really question yourselves. Am I creating the blocks? Can I break free from the shackles of what life is “supposed” to look like? Whose cookie cutter am I fitting into? If you can answer these questions honestly then you’re taking your first step to breaking the mold.

My journey went a little like this:

I studied my degree while working 3 different jobs to make ends meet and always vowed to have enough savings that when I go on to do my master’s that I wouldn’t have to work. This was the lightbulb moment that drew me to warmer climes.

I knew a hand full of people that are doing exciting things all over the world. I decided to test the waters and reached out to a friend (Gareth) who had always mentioned I should go to visit him in the Cayman Island.

I started by asking Gareth for a list of bars in his local area. Once I had a list I harvested their email addresses, once I had their email addresses, I was able to send my CV and covering letter to all of them on mass, it didn’t matter if they were looking for staff or not, I just needed to cover all bases. I am lucky that I was able to secure a skype interview and was offered the job right away.

My number 1 rule about travelling to a new location with a view to living and working there is: Know someone with a couch! (Thanks Gareth) If you have someone who will let you stay on their couch until you get yourself settled then, in my experience, you will be golden. This is the way I’ve done it many times over and it is always been successful. There are basic things you can do to repay your keeper such as cleaning, cooking, and making sure you don’t get in the way. Make sure you ask about boundaries, timings, and special requirements before you get comfortable, so you know you’re not encroaching. With these things in mind, you can be sure that when you leave, you’ll be missed.

There is often a hefty amount of paperwork to deal with when relocating but it’s all within your reach. All you need is a checklist and some patience, and you will make it. It is often what puts a lot of people off but I’m telling you, some of the most worth while things you can do in life require and OBSCENE amount of admin. Just power through.

I landed in Cayman with $100 USD and a pocket full of dreams; it was time to start grafting. I spent the first 4 years working in hospitality, for the most part in a small vegan café where I really found my groove. This establishment was so inspiring that it led to me write a rap that escalated quickly, and we ended up shooting a music video. During this process I met the love of my life. I created great rapport with pretty much all the clientele. One business owner spotted something in me that I was becoming more aware of, a value I was adding that couldn’t be replicated. I was asked if I wanted to join a start up tech business, I was ready to grow so I took the leap.

The lesson I want to impart is this: no matter how good you think you are at your job, no matter how over it you might be, you never know who is taking note, you never know who might see the magic you bring to the table. So, bring the magic, go the extra mile, make your customers feel amazing, transfer the energy. I have spent my life being un-refutably positive, even through the dark days (and believe me I am skirting WAAAAAY over the dark days) It pays to keep your chin up in your work environment. Taking risks is scary, SO scary. But the rewards are plentiful.

We all have the potential to do great things, every single one of us. It just takes that first scary step over the edge. I did all of this on a tight, tight budget, you don’t need to start with cash in the bank. If you can work hard, you can make this happen for yourself. Just a little bit at a time, save for your flight, reach out to that friend, do your research on permits etc. and take the leap. You’ll learn so much on your journey, the biggest lesson is learning to let go of the fear and use it as fuel to break out of your comfort zone.

Good luck on your journey!

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