When a Stranger Locates Your Front Door Through An Instagram Photo
And, one of the biggest reasons I'm on Substack advocating for your Wildhood.
If you’ve been following this publication for more than a minute, you’ve probably noticed that plenty of my stories begin something like, “This one time in Jamaica….”
I mean, even I get sick of it sometimes 😂
But the truth is that my odyssey as a destination writer occupied a significant chunk of my life. By default, most of my wild, weird, and incredible life sagas happened under the influence of that island.
This chance Instagram encounter and several others like it are no exception. Because I specialized in a single destination, my audience was much more intimate than your average online voyeurs.
They followed my stories like rats followed the pied piper and quite often, they BECAME the stories.
This one morning in Jamaica (there it is 😁), I posted a photo on Instagram, taken from the verandah of a vacation condo I was hired to promote. This was the exact photo:
I captioned it with, “Good morning from beautiful Runaway Bay!”
Ten minutes later there was a knock at my front door. Upon opening, a lady stood there asking, “Are you Kristi?”
Indeed, I was.
She introduced herself as Wendy, a fellow Canadian and avid reader of my blog. She happened to be renting one of the condos in the same complex and said when she saw the photo she knew exactly where I was.
Once she introduced herself I instantly recognized her name from past online interactions.
As it turned out, she lived in Jamaica and owned a bar across the road. So, of course, this just turned into yet another connection for me. Later on, I ended up promoting her bar on my blog.
Small world, BIG coincidences.
Some people reading this might consider it slightly creepy that internet strangers knew my whereabouts in a foreign country. But it had happened so frequently over the years that it became fairly normal and occasionally fortuitous.
It became good for business in the long run.
When you’re well-known within your niche it’s not uncommon to step off a drunk karaoke stage at the beach after doing your best Tina Turner, and have a random man approach you asking, “Hey, aren’t you Kristi from the Jamaica blog?”
Not my finest performance but I’ll be damned if it didn’t make me relatable. Everyone does drunk karaoke on vacation, don’t they?
Hands down, my favorite random but not-so-random encounter with strangers…
It happened in 2017 and it was by far the most coincidental meeting.
At the time, I was living on the fairly remote southern side of the island. Tourists rarely showed up in those parts because the industry wasn’t as developed in the south.
I received a call from the manager at one of my favorite little guest cottages in the area. He had called to ask if I would drive over and meet a European couple who needed assistance planning the rest of their island jaunt. Of course, I happily obliged.
Upon arriving, I was introduced to the cutest young couple from Poland. They were backpackers and eagerly filled me in on their epic two-week trekking plans around Jamaica.
Honestly, I was a little shocked that they ended up in such an untouched area of the island. The South Coast isn’t rookie territory so I felt compelled to ask them how on earth they found it.
They explained that they’d found this cute little cottage on a blog called Jamaica My Way. I had to LOL because that blog was ME! This little cottage didn’t have a website but I had written about it several years earlier and they read my review.
As a result, the couple offered to pay me to take them out that night and show them a good time on the south side. (I’m just now realizing how prostitute-ish that sounds 😂)
Before they departed on their next leg of island-hopping they gifted me with a coffee mug from Poland. They had carried several gifts from home to give away to locals they may meet on their expedition.
I still have that coffee mug today.
Throughout my decade of being a self-made destination specialist, these stories played out over and over again. I can’t even count the number of times strangers approached me asking, “Hey, aren’t you Jamaica My Way?”
Indeed, I was.
And it was one helluva great feeling knowing I had helped so many people travel and live well.
NOTE: I sold my trade name and assets in January 2023 so if you find Jamaica My Way on Google I’m no longer affiliated.
One of the biggest reasons I decided to show up on Substack is that I lived a fantasy life as a destination writer. Now I want to inspire others to walk the same road, whether that be a dirt path in the bush or a well-paved highway here in civilization.
The #1 question I was asked for many years was:
“How the hell did you afford to travel so friggin much?”
They usually asked right after learning I’d been to Jamaica 36 times (and didn’t bother coming back twice!)
The answer is a long one but the short version is that I just figured it out.
During my fifteen-year love affair with one small island, I was pretty blessed in the ‘accident’ department. Meaning, I tried a bunch of things to make money, eliminate travel costs, and create a lifestyle that filled me with joy… and I accidentally found out they worked.
I desperately wish I’d had this information back in my noob days.
Now, I’ve settled down long enough to flip through my crate full of journals and realize that this is totally worth sharing. If for no other reason than to pass the baton to other lunatics who have an insane addiction to their favorite pin on the map.
Newsflash: Your addiction is NOT insane so please…DON’T STOP with it! Do not listen to your family members when they say, “OMG you’re going there again???”
There are a thousand ways for you to thrive financially, professionally, and personally, using nothing but the destination you love to be in, whether it’s right at home or a thousand miles away from it.
Because who doesn’t want a coffee mug from Poland? Or an Instagram creeper to show up at their front door?
Your answer might be, “Not me!” but hey, if the Polish and the creepers come bearing financial tidings, why wouldn’t you want it?
SO…..
While I’m sending out Wildhood Wanted emails to you every week I’m also madly typing stuff behind the scenes, trying to compile and deliver this specialized journey in a way that other noobs will understand and be able to execute.
While there’s a bit of a process involved in getting started it can be dished out in a time frame shorter than six years, which is exactly how long I spent a shit ton of travel dollars before realizing there had to be a more financially sound way to sustain my travel addiction.
I don’t want it to take that long for you.
Stay tuned. I only type 55 words per minute.
In the meantime, what is the most randomly coincidental moment you’ve had while travelling? Maybe you bumped into your next-door neighbour in a restaurant 3000 miles from home?
Please share!
PS: These are the kinds of escapades you could embark on just by being in love with your favorite vacation spot:
I think I would be too freaked out by someone geo locating me that was to make any connection! 🤣These friendships seem great though. I'm a jealous introvert looking through that window from outside.
I can think of a few times I've traveled to a city for a spontaneous visit and randomly run into someone I hadn't seen for a decade or more. It's almost expected now.