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I love random stories like this. In my book, The Wisdom Found in Hen's Teeth, the plot revolved around how rare things aren't really rare at all. I talked about friends who won the lottery, met Oprah on the street, were shot by their ex-wife, were hit by a flying port-a-potty on the highway---that sort of thing. I would have included your ninth caller winning!

I won an essay contest (my favourite!) in 1994---first prize was a return ticket to San Jose, Costa Rica. That was it! Just the flight---for one person! I wrote about my semi-dismal time volunteering for three months in the Costa Rican jungle (insert trench foot, parasites, malaria here) and ironically, won a trip back to the scene of it all. I did things differently though---ie. less trench foot, no parasites (that I was aware of) and skipped the malaria. What a fun start to your Jamaica roots!

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That's so awesome you've won trips as well! I wish I wouldn've won trips for one lol. This first one was great with a friend but the second prize trip, it was actually difficult to find a travel partner on short notice. And even more difficult to find someone I knew I'd enjoy traveling with.

Your Costa Rica tales sound like shit that would happen to me LOL!! Do you follow Marlo of What an Adventure? It's all about her life of living in Costa Rica and all the weird & wonderful parts of running a hotel there.

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What was the second trip you won? I thought you were counting the San Diego one with your mom?

I almost went to Copenhagen with my friend Candice---her boyfriend was too anxious about flying and backed out. She had won a trip for two courtesy of Carlsberg through a bar contest but they wouldn't allow a name change after she signed things so she went solo.

I do follow Marlo! I love those "I opened a hotel ______________" (anywhere) genesis stories. My fantasy self would open a boutique property somewhere hot with mangoes dropping out of the sky.

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I swear, even though I’m comfortably rooted back home now and loving life, I would ALSO love to open a small boutique-ish spot. I’ve worked on both sides of hospitality for a long time so I know I’d be a fantastic host 😁

Oh, and the second trip I won was also Jamaica (trip #4). That story is a chapter in the future and that win was really quite amazing and bizarre. Stay tuned for that.

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Congratulations Kristi for Chapter 1, it certainly brings back some memories of Jamaica. Thank you for sharing the loss of your son, a pivotal moment in your life. Bring on Chapter 2!

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Thank you Cerina! This has been so nostalgic for me, I'm really looking forward to more!

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Kristi weirdly enough I got a blast from the past from your radio call in of all things. I remember listening to the radio in the bus when my Mom used to be a driver at my school. We'd hear people call in and win prizes all the time and hearing them scream on the phone was always fun. Anyway, I also remember my first time exiting a plane and walking right onto the tarmac. What a fun f*cking word by the way. Tarmac. Thanks for this fun first chapter.

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Hahaha yes! Those radio contests are so legit! A hundred years ago, my mother also won a trip to San Diego from a radio show.

I'm having SO much fun reliving all of this by rewriting the book. Now I'm going to check on yours. I think it's awesome we're running side-by-side with our travel memoirs 😁

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I love that you’re (re)serializing your book. Keep it coming. 🙏

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Thanks Zach! It's been really fun (and super nostalgic) to dig into the past and try mixing it with the present.

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I found you here on Substack when I first joined almost a year ago. Not knowing the 'how you got started' part, it was great to make that connection through Chapter 1. Thanks for sharing. Isn't a wonder how a place really can speak to you and get in your soul? I think curiosity made you do it...made you wanna get off that bus and find out more!

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YES!! And I’m SO glad it did. I sometimes wonder what my life would have been if I’d been just satisfied with that first trip and then done, like so many others I’ve been to. The only other destination that has captured me in the same way is New Orleans. Something about it…

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This is such a fun beginning to your serialization. I can't wait for the next installment, Kristi.

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Thanks Paulette!! It really is fun, isn’t it? Winning trips was always a great conversation starter.

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I also have a deep love of Jamaica. I’ve been there twice, and would return in a heartbeat if someone paid for it 🤗

I’m so glad you’re serializing your memoir, and I look forward to reading more!

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Teyani, you just wait because that was my story as well! It cost me a fortune to be in love with Jamaica...UNTIL I figured out how to get paid for it. But before that, I spent 6 years financially feeding my addiction 🤣

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Love this. I’m always excited to see your stories from Jamaica.

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Aww thank you. That means a lot because I know this is such a small niche and I figure lots of people might get bored hearing about the same place all the time.

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Sounds to me like it was Sean Paul who actually ruined your life.

But there’s no going back. You can’t unsmoke, undrink and unsee all that stuff. I guess you’ll just have to live with consequences of your trip win no matter what.

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I mean, if we REALLY want to break it down, it's the radio station that ruined my life lol.

Thank goodness it all turned out for the best...even though my liver and my lungs are probably glad I called it quits after 15 years.

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Humble brag: I've won a lot of things, but never a trip or vacation. I've been trying!

I did not know about your son prior to this read. I am so sorry. Telling the stories of grief is so very hard to do.

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Winning a vacation is otherworldly, that's for sure!!

And thank you for the virtual hug. It was weird writing that line because in the original book there were only 2 life-altering events...but to make it make sense 15 years later I had to include my loss.

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Mmmm that is so brave.

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That is a pretty epic way to start chapter 1! I know that tour bus feeling well. My wife has dragged me along on a couple of Caribbean cruises over the years. Its frustrating to see a fascinating place, but be ushered along a canned "experience."

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Yessss! It is so frustrating! Also, having read your DR saga where you were pretty much thrown into local life, it's such a contrast.

PS: I have a stomach rebellion part way down the road in my book 🤣 It happened on trip #4 and I literally thought it was my death.

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Oooff!! Mine wasn't nearly that bad. Sounds like a true right of passage! 😬🤣

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I'm so excited to read these adventures and revelations here!

I know that feeling of "get me off the bus" to well. When I backpacked through Europe, the first thing I did in any city was take a double decker bus tour to see what the tourists would see, but instead, I watched all the locals and wished I knew them personally so they could show me around rather than the stock tourist show.

I've been to Jamaica once, as a stop on a Carnival cruise. I think I was a level of not quite drunk the whole time and I remember very little. It was too touristy. I didn't like it. I just told Deanna Thomas that I intend to visit her there someday, get the local experience.

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Yeah, if you arrived on a cruise ship you didn't see "Jamaica" for sure. When I lived in Ocho Rios in 2011 it was so quaint and "local" at the ship dock but over time, they kicked all the fishermen locals out, tore up the beach and built a massive duty-free shopping center. THAT pissed me off. Those fishermen did good business on the beach before then.

And yes, if you ever get to visit Deanna, you will see REAL Jamaica because I know where she lives. Tourism hasn't completely gutted it yet.

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same thing has happened to Maui in many ways.

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I can't wait for chapter two! I've always wanted to go to Jamaica, but my husband will NEVER take me EVER!! So unless I meet a girlfriend willing to go, I'll never experience what you did. The closest I've come is during a cruise I was lucky enough to afford, I went to Roatan and snorkeled for the first time ever, and loved it so much that I wished we had time to do it again!

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Ahh I'm so glad you're here to follow along! I had no idea whether or not anyone would want to read this so I'm happy a few people are into it 😁

Why won't your husband take you to Jamaica??

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He thinks its too dangerous. He is convinced the cartels can attack you anywhere even if you're in a fancy resort. You are so brave to go back and explore the REAL Jamuaca

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If I had a dollar for every time someone asked me if it's too dangerous, I would have retired long ago lol. I always told them, "Well....I've done the entire island as a single white foreigner and I'm still alive...sooooo...."

My take on it is that EVERYWHERE has dangerous areas but your likelihood of finding one of them as a tourist is very low. You're more likely to get hustled by vendors than attacked by a cartel 😁 Having said that, it has gotten significantly worse over the years. The last time I went was in 2019 and I had to drive through military checkpoints on both ends of Montego Bay. It was disheartening, to say the least.

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Looking forward to reading more.

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Thanks Nancy!

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"I’m Canadian. We don’t have palm trees, colorful houses, or a vibrant dialect that sounds pleasant even when you’re telling someone to go suck it." Yeah, mon. And all that wonderful music: ska, reggae, dance-hall and whatever they call it nowadays...

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David, they still call it all the same thing and maaaan, is music ever a massive influence there. I got fully immersed in it, so much that I had no idea what was mainstream in Western pop culture anymore.

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I have won a vacation! Actually my friend won it and took our whole friend group (8 of us) to Mexico for a week so you and I are proof that people do win those contests! The thing I found amazing was the sponsor, Kraft Canada, did nothing. No photo opp to market their brand, no mention of the winners. It was surprising but...off we went and a great time was had.

I'm reading about the magic of coincidence right now which makes this chapter even more fascinating to me. So many unknowns had to fall into place for you to make Jamaica your other home that it may have been more than coincidence...who are we to say?!

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That's amazing you've also won a trip!! And for 8 people!!?? How awesome 👌 A million years ago when I was a kid, my mom also won a trip to San Diego from a radio morning show and she took us kids.

If you enjoy the magic of coincidence, you'll love this journey. It's a major player in plenty of what I did there. Thanks for tagging along Donna!

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Donna, that's an odd destination for Kraft to promote! What was the connection? How did your friend win that one?

Kristi--my dad won a family pass to the African Lion Safari (in Cambridge, Ontario, NOT Africa) for roaring like a lion on the local radio station. It foreshadowed things for me too and inspired future safaris in Africa, not Cambridge!

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