That Time I Took Myself on a Cruise in The Caribbean and Ended Up As Kirstie Alley’s Executive Assistant

My life has been a lot of things, but boring is not one of them. I owe this in its totality to my curiosity and spirit to follow that all knowing ‘pull’ (not to be confused with that self-justified, talk yourself into it, ‘push’). There was one occasion in particular when I followed that pull and it slung me out to the moon and back.

I was moving from Ireland to England and while the paperwork for my work visa was doing ‘the rounds’ in London, I made a quick trip to Georgia for some grits and buttermilk biscuits. I knew the paperwork could take a few weeks and I had braved the Irish rain so courageously for three years that I decided I would treat myself to some sunshine down in the Caribbean while I was home. So I booked a cruise and off I went.

Traveling alone has never been frightening to me and some of my best friends today are people that I met on solo journeys. You are inclined to strike up ‘random’ conversations and spend time doing what you want and need, which for me has culminated in huge personal growth over the years. I’ve gotten to know who this incredible girl really is, not just who everyone else expects her to be.

On this one particular trip I met a group of guys and gals from Los Angeles and we quickly became friends. We had a fun week discovering Barbados and Saint Lucia together and when it came time to say goodbye they invited me to come visit them for New Years. As it was only a week away, I thought it shouldn’t interfere with my London timeline and I had never been to Los Angeles… so… why not?

As it turned out, they were part of an A-list tribe in the city and I found myself visiting somewhat of a twilight zone. On one occasion I was at Kirstie Alley’s house and she and I got into a conversation about my travels. It was a pleasurable conversation and evening but nothing specifically noteworthy, or so I thought.

The next morning I went for a hike up to Griffith Observatory and when I got back I had two missed calls from an unknown number. I checked messages and there Kirstie was… on my voicemail… inviting me over that night for dinner… because she had something she wanted to talk to me about… I sort of sat there totally confused but eventually called her back and accepted the intriguing invitation.

Eight hours later I was no longer moving to London, but instead to Los Angeles to work and live with Kirstie Alley. I had managed my own business previously and she wanted me to help her with hers.  At the time she was the spokeswoman for Jenny Craig and needed help organizing her various business ventures and felt I was someone who would be good at that. As I was listening to this role that she wanted to create for me, based on a one-hour conversation we had had the previous night, it occurred to me that I didn’t actually live in Los Angeles. I barely had a toothbrush and a couple pairs of underpants there, much less a home. I reminded her of this substantial reality and she folded that nicely into her proposal and offered that I live with her. It was all dream-like and my curiosity won in the end.

I turned down my work visa for London and had everything shipped back to the U.S. It was a wonderful experience, although life there never managed to evolve from the dream-like state, but instead morphed into an introspective catechism. It was a fun time and I got to meet attractive people that were big faces on the screen, but after a while I began to realize that what is deemed as ‘interesting’ or ‘important’ is a very personal and subjective thing. For me that life was neither interesting nor important, despite what the media would have you think.

It was a world of fad diets, plastic surgery, and expensive face creams designed to make you think that the best version of yourself can be bought. For me they were empty promises and nothing more than a lesson along my journey. Although Los Angeles was not a space of gravity for me, it helped me realize that no matter where you go, time spent enjoying yourself is never time wasted, and at the end of that pull what I found was the coolest version of Ashley.