Cuba: Not All Who Wander Are Lost

I went to Cuba for one purpose only-to collect content for a new online course about iPhone Street and Portrait photography.

I came back, for sure, with the goods, and more, but it took me three days to get started.

I arrived exhausted. Cuba was the last in a long series of projects I had been working on, over the past 4+ months.
I’m sure this is far from reality but, it felt like, I had been working, night and day, 7 days a week, for longer than I can remember.

My online coursework, especially in the preplanning stages, is tedious and laborious.

I have to write scripts, scout locations, develop detailed shot lists, line up subjects to shoot, polish up my gear, arrange ground support, etc.

For the first handful of days, after my arrival in Cuba, I joy couldn’t seem to get it going.
Rather than follow my trip notes and production plans, as I usually do, I said the hell with it and wandered the streets instead.

Not all who wander are lost.

My efforts have always been intentional, deliberate, planned, and calculated from the beginning of my photography journey.

Even my casual, photographic ramblings and roaming, are, more or less….. “intentional wanderings”.

Wander, in a general sense, for most people, implies aimlessness. Not for me.

For me, as a photographer, wandering takes on a more nuanced definition.

It means, in practical terms, that I don’t have a specific itinerary or roadmap or even a shot list.

Instead, I’m shooting what I see and following my instincts, impulses, and intuition.

Wandering, with the camera in hand, is a freeing experience full of surprises and gifts.

This is a tiny snapshot of what wandering looked like to me, in my first few days.



Jack Hollingsworth