Serious Case of Deja Vu

Flying back from an inspiring time with the tech team in India, I found myself hit with a serious case of déjà vu.

For the fourth time now, I was knee-deep in reconfiguring the PickYourPlayground directory. This wasn’t just another tweaking of the platform; it was a substantial effort that required my full attention, and, if I’m being honest, my full heart. And let’s not forget, this journey hasn’t come cheap. Since 2005, I’ve poured hundreds of thousands of hard-earned personal cash into this business. If raising a child is expensive, well, raising this baby is just as costly—if not more so. Between the hours of work, the personal sacrifices, and the financial commitments, it’s a rollercoaster ride unlike any other.

But just like with children, businesses go through different phases. Each phase requires a new level of commitment, new energy, and at times, a deep dive into your emotional and financial reserves. In the early days, I’ll admit, there have been several moments when I seriously considered closing the doors and walking away. What entrepreneur hasn’t? But here’s the thing: I love this brand, I adore the name, and I believe in the concept with every part of my being. Letting go? That’s never been an option.

The more we travel, the more adventure activities we take on, and the more we connect with owners and seekers in the adventure space, the more we realize just how needed PickYourPlayground is. The feedback we get is heartening. “There’s just nothing like this out there,” they say. Or, “Thank goodness, we’ve been waiting for a platform just like this.” Comments like these remind us why we continue to push forward, even when it feels like two steps forward, three steps back.

But here’s the thing: we’re really good at getting back up. And if there’s one thing I hope you take away from this journey we’re sharing, it’s that you should be too. No matter how many times you stumble, what matters is finding the strength to rise just one more time. That’s the spirit that’s kept us going for years—and it’s the spirit that will keep us going in the future.

As we continue to roll out PickYourPlayground in Dubai, the momentum we’re seeing among activity owners has been amazing. We’ve already started to see interest from like-minded entrepreneurs, and that’s exciting. Jack even kicked off an Owners’ WhatsApp group this week, and that came as a result of a request from an Activity Owner! It’s been fantastic to see small business owners in the adventure and tourism space eager to connect, share ideas, and support each other.

If you’re in this space and would like to connect, we’re here for you. Feel free to reach out to us, drop us a note, and make sure you’re on our radar. We have big plans for this year, and we’d love to share that journey with you.

Here’s to creating something amazing together—one step, and sometimes one slide, at a time!

Yours in all things adventurous

Dianne & Jack

PS:          Join the Journey: If you’re an adventure activity owner or someone passionate about this space, don’t hesitate to get in touch! Whether you want to be part of the Owners’ WhatsApp group or just want to learn more about what we’re working on, we’d love to hear from you. Together, we can make this community stronger and create something truly special.

PSS:      Photo: In case you’re wondering, and have read this far, the photo is of our Dev Team who managed to get us live on Jack’s birthday. It’s the best gift anyone could have given him!! 😉