
This is an adaptation of my weekly newsletter, Adventures Big & Small. If you want to receive emails like these, click here to subscribe.

Fair warning, this is a long one. Worth it, of course 🙃
The Inspiration Series is getting really close to launch, but one thing throughout the process has been illuminating. At some point, I started asking questions like “when do I become more of a guide than a photographer?” or “can we go stand-up paddleboarding?” Will my insurance cover this?
I’ll spare you most of the details (spoiler alert – motorcycles are fine, stand-up paddleboarding is not) but the sentiment is something I think we all need to be talking about more.
A quick search shows that 29 people died on stand-up paddleboards in the U.S. in 2024. Only 11 in 2023. I didn’t look up motorcycle deaths because we all know that’s a depressing number. And yet my insurance will fight for me if my clients get hurt on a motorcycle during a photo shoot. But they’ll run the other way if someone sprains an ankle while paddleboarding.
It’s the reasoning that I find most unsettling. Apparently, cycling is “normal” while SUPs are fringe. Photographing a family on motorcycles is seen as me tagging along on something a family might otherwise do. But stand-up paddleboarding? Who in their right mind would do that if a photographer wasn’t watching?
As you likely already know, I grew up on an island in the Caribbean. My parents handed me the keys to a questionable little boat at age 14 and turned me loose. I’ve heard them say maybe they gave me too long a leash. It’s hard to argue.
But (and I can safely say this after surviving my teens) I wouldn’t trade it for the world. It was formative. It was empowering. It taught me to make real-world judgements about risk. I didn’t care what was “normal.” I just wanted to keep the boat floating and make it to the next island.
I think what scares me most about modern litigation is the slow drift toward “normal.” When the legal system pushes businesses toward the center line, businesses push society — through marketing and the experiences they offer — toward that same center line. Slowly, surely, we all inch closer to the middle, until the edges barely exist.
And yet. We talk so much about how we value depth and breadth and variety and texture and awe in our lives.
You don’t find much of that on the center line.
So I think we need to push back. As individuals. As parents. As a society.
We need to teach our kids to look at the world with an open mind. “Normal” is not always great, or even safe. Risk is not black and white. The best parts of life are full of nuance.
I want my daughter to grow up learning how to intentionally engage with that nuance.
All of this doesn’t actually change my Inspiration Series very much. I’ll have to table a few ideas for now, but it’s also going to lead to alliances with licensed outfitters and guides, which I think will be awesome for everyone.
If anything, it makes the whole thing feel more essential. I want to meet you near the edges of “normal.” Thoughtfully. Safely. In a way that brings your family closer as you grow together.
More soon,
David

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