“Hey, do you make YouTube videos?” It was the second time I’d been asked that question in a week. It happens a few times a year on this small island. For somebody with just a couple thousand subscribers on YouTube that’s a lot. And while I have asked my wife to refer to me as the island king, she has yet to oblige.
“Hey yes I did, sorry, I’m just on a call…”
“Oh I’m so sorry, I just wanted to say I watched your videos before moving here, they were so helpful. Thank you.”
I was caught off guard by this stranger’s kindness, “Oh wow, I’m so glad. I’m sorry I don’t mean to be rude I’m…” I gestured lamely at my phone.
“I’ll let you get back to your call.”
“Sorry again, nice to meet you. Thanks for saying hi.”
It’s been two years since I’ve posted anything on my YouTube channel. Three since posting something longer than thirty seconds. Running into people who have moved to Cayman and watched my videos before they made this huge life decision is bittersweet.
I was early to YouTube. Especially for a kid in South Africa with a slow internet connection. I was convinced I’d be a filmmaker in spite of the real world pushing me towards accounting. I learnt some great skills and had a ton of fun with friends, but my videos never got more than a few hundred views.

When I moved to the Cayman Islands, I vlogged my new adventures. Some of those videos got thousands of views. That was huge for me. Try not to think of the MrBeasts of the world and the mindless scroll of short form content. Imagine trying to get a thousand people to sit down and look at something you made for more than a few seconds. That’s a crazy feat.
More importantly I loved making them. It was an excuse to get out of the house each weekend when I was single and do something fun, find another beautiful spot to film, or take on a challenge with a friend. I was motivated by the output of a cool video, but it was never really about the videos.
For example, I was alone on island for my 28th birthday. So I asked a friend to rent jet skis with me, something I hadn’t done before, and I decided to bathe in some cereal just because. The video is silly, but it made for a memorable day.
Over the last few years I got married, started to build a career, and had a kid. Incredible, beautiful milestones. And with each, my commitments, priorities and time shifted. Slowly, not suddenly. I made fewer videos until I stopped altogether.
The videos I made over that period became time capsules. Not polished productions, but real, happy moments edited together to watch back and reminisce over year after year. Like our wedding. There's a moment in that video where my new wife and I get caught in a sudden downpour and run laughing to the car. It makes me smile every time I watch it.

There is a sense of loss for those video-making days. The days where I would spend an entire weekend filming and editing a video, and then keep refreshing the analytics through the week to see if one more person had watched it. Trying some ridiculous activity, eating something strange or travelling somewhere new just because it would make for a good video. I can't just disappear for a weekend to film something anymore. Nor would I want to.
With each stage of life we go through versions of ourselves. Some who we’ll never see again, and some who get revived in different forms. While I may not have time to film and edit the way I used to, I still need a creative outlet. I'm still a storyteller at heart. It's even in my social bios so it must be true. It's why I started this Substack. I get to tell stories without all the more time-consuming parts of making videos. And now, instead of capturing moments on camera, I'm capturing them in writing.
Perhaps as my daughter gets older, if it’s something she’s interested in, we could build memories around making little films together. Maybe it’ll come full circle. Maybe it won’t. My hope is less about her loving the same things I do and more that we’ll find something creative we love doing together.
Those old videos are still up there, their numerical performance long forgotten. Every now and then they make someone laugh, or more likely cringe. Sometimes they’re even helpful to a newbie thinking about moving to this rock in the ocean.
Last week it happened again. I ran into someone at a hot food counter who had moved to Cayman only a year earlier. I took out my earphones, pausing the Diary of A CEO podcast and my entrepreneurial daydream to have a chat. One of those views I’d once gotten so excited about was now standing in front of me, saying hi.






The evolution continues!