“But what if it doesn’t work out?” he asked. “Yeah, but what if it does?” she replied.


What a whirlwind ending to 2018. A most unexpected person wandered into my life at the most unexpected place and time.

In hindsight, our meeting seems fateful. Changing the trajectory of those weird final days of my year. You know, the ones where you aren’t sure what day it actually is, whether you should be working or playing, and asking yourself each morning if it is OK to pop open the bubbles before noon.

And, because the Universe apparently has a sense of humor, it threw this guy into my lap in the midst of those days. I guess just to mix things up a little more.

But despite my confusion, this handsome stranger gave me some much-needed inspo. In life and for this blog. At a time when I was feeling really empty and uncertain. He also got me to finally try yoga. So, thanks universe. You really do have a plan, don’t you?

2018 went out in spectacular fashion

Anyway, the exchange above came from a conversation I had with my new friend over coffee one morning at my favorite beach bar. With the endless Caribbean Sea spread out before us, we were discussing life and relationships. Pondering why we make some choices and avoid others.

When he first said them, the weight of his words didn’t really deliver their full punch. That only came a few days later when I was reflecting on everything during one of my solo, early morning beach walks.

His question reminded me there are a lot of things you can be afraid of in life. Failure being close to the top of any list. I mean, nobody wants to fail. Nobody wants to experience the pain of having something you cared about not work out. It sucks. I know this first-hand.

But, really, there are no guarantees in life – other than death and taxes, as they say. And nothing lasts forever, either. Relationships end, either through death or a break-up. Jobs are lost. Moves don’t always live up to their initial promise.

Where I do my best thinking.

Understanding this, it made me more than a little sad to realize that people avoid choosing something solely because it might not work out down the road.

Long gone are the days where people lived in the same place their entire life, worked the same job for 50 years, or even stayed together with the same person for even half that long. And those kind of changes are also likely to cause you a little (or a lot) of pain at some point.

But why be afraid of pain? Without it, how can you experience the real pleasures in life? Or even know what pleasure truly feels like? Sure, there might be some superficial good times along the way, but in the end, the real memories that you’ll hold onto and treasure – the ones that bring happy tears to your eyes, the ones that presumably will flash before your eyes in the moments before your own death – only come with risk. The bigger the risk, the sweeter the experience.

If you don’t take a chance at all, you’re shutting down the possibilities for these kind of memories altogether. Whether it’s a relationship, job, where you live, whatever. And thinking about a life devoid of rich memories like this makes me sad. Really, really sad.

I think about my own failed marriage. While it imploded in unexpectedly spectacular fashion, that doesn’t negate the good memories made over 12 years together. Even today, seven years post-divorce and without a word exchanged with my ex, a good memory from those times occasionally pops into my head. All I can do is smile and be grateful that I get to remember.

Celebrating my birthday in Paris would not have been possible if I had said no to taking a chance.

Likewise, my brief foray into life in the Channel Islands. Was Guernsey everything I hoped for? Fuck, no. If I were to tally every experience during my time there, the final determination would be = miserable. But still, even though we got on like oil and water, my time on that inhospitable chunk of granite did have some positives. The opportunity to live and work part-time in London, the chance to say I worked for a billionaire Italian count, being the editor of a magazine, and fun memories exploring the UK and France (Paris is overrated). None of that would have been possible if I had declined the move, worrying that things might not work out.

The same for my decision to uproot myself all those years ago. Was I guaranteed that things would go well when I traded my old, stable life in Seattle for the unknowns of a Caribbean rock? No way. Has it been smooth sailing the whole time? Hell, no. But if I had said no to trying in the first place, I wouldn’t have all the wonderful memories I’ve made here. The friends I’ve made. Or the feeling of bliss I still get when I drive home from the beach at sunset.

None of these memories and experiences would have been possible if I had asked “What if it doesn’t work out?” and decided it was better not to try at all than risk being exposed to pain down the road.

I could go on, but you get the idea.

And now there is a new year spread out before all of us, brimming with infinite possibilities. It will deliver opportunities and challenges, as every year does. The difference is how you approach what the universe sends you.

As you move forward, I’d encourage you to step outside your comfort zone and welcome all the opportunities (disguised or obvious) that come your way. And try not to ask yourself “What if it doesn’t work out?”

Instead, get excited about the possibilities when it does.

Got questions? Want to know more about island life? Thinking about making a big life change (whether that includes an island or not)? I’d love to hear from you. Check out this post or send your thoughts to hello@theadventuresofislandgirl.com and let’s connect.

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