When the Photography Gods Don’t Smile Upon You

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Old San Juan, Puerto Rico

If I were a more professional photographer, my travels would be very different.

I’d do a lot more research beforehand, scoping out the best places to take the shots I wanted. I’d wake up before sunrise on a regular basis (the horror!) and plan my days around the sunsets. And in case of bad weather and bad light, I’d be completely sidelines, unless there was something inside I would want to photograph.

I’d be prepared to spend long stretches of time simply waiting for conditions to be perfect before pressing the shutter.

Making a living as a full-time travel blogger is hard enough; making a living as a travel photographer is arguably even more difficult and requires more hustle. And like I’ve said about freelance writing in the past, I hustle enough already that I don’t want to add hustling in another industry to my agenda.

Old San Juan, Puerto Rico

That, and there’s the fact that sometimes you just have bad luck for photography.

Sometimes the light is bad. The weather is bad. You’ve got limited time. Or the place you intended to photograph is a lot more of a challenge than you thought it would be.

To my dismay, all four of those things happened to me in Old San Juan, Puerto Rico.

Old San Juan is gorgeous — and well worth a visit. I loved exploring the old city and you should make it a priority of your own.

But I was shocked at how difficult it was to photograph. I didn’t expect that the streets would be so narrow and that virtually all of them would have street parking. The incoming bad weather made things far worse.

Old San Juan, Puerto Rico

And our poor, sweet guide. He was so knowledgeable and enthusiastic, but I don’t think he quite got what we were doing as bloggers and not regular tourists.

“Listen,” I would tell him, “I’m nervous that we’re about to lose the sun. We need to get pictures of the colorful houses in Old San Juan before that storm rolls in.”

“It’s not going to rain!” he replied. “It’s just raining in the rainforest.” He gestured into the distance.

“Okay,” I told him, “but I need to get pictures with blue sky, not those dark clouds coming in. Can we go see the colorful houses now?”

“Yes!” he announced. Then he brought us into an underground fort.

Old San Juan Fort, Puerto Rico

Yes, it’s a good fort; yes, it’s a UNESCO World Heritage Site. But it killed me that we were inside when we could have been taking good photos in that beautiful light! By the time we emerged, the clouds had taken over.

He assured us we were going to see the colorful houses next…and then took us to a historic but largely unphotogenic area without any houses.

Old San Juan, Puerto Rico

I think I gritted off half my teeth that day.

We did find the colorful houses eventually. But by that point, the sky was so dark that it made the colors come out much worse. I tried my best to salvage them; I’m not happy with the results.

Old San Juan, Puerto RicoOld San Juan, Puerto RicoOld San Juan, Puerto RicoOld San Juan, Puerto Rico

Honestly, I hate most of the photos I took this day. Not only were the conditions bad, but I also felt like I was so off my game. I’m usually much better than this.

Old San Juan Cat, Puerto Rico

It says a lot when you visit a beautiful city and the best picture you take all day is OF A CAT! (But that cat, though…)

It just goes to show — not every travel experience will be a home run. No matter how well you think you’ll an enjoy an activity, no matter how meticulously you plan in advance, not everything is going to line up. Make peace with that early and often.

That said, by the end of the day, I had one photo of Old San Juan that I actually liked.

Old San Juan, Puerto Rico

Perhaps all I needed to do was to stop fighting the city and just lean in and take what it gave me. That picture has cars. It has people. But it feels more like Old San Juan than any other photo I took that day.

Essential Info: In San Juan, I stayed at two properties: the Hilton Caribe and the Hilton Condado Plaza. Both are excellent choices but I much preferred the Caribe and would jump at the chance to stay there again. Low-season rates at both properties start at $179. Find more hotels in San Juan here.

I visited Puerto Rico on a campaign with Puerto Rico Tourism. All opinions, as always, are my own.When the Photography Gods Don't Smile Upon You