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

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67 thoughts on “When the Photography Gods Don’t Smile Upon You”

  1. The last sentence says it all. And just like I like to read about real travel experiences with all the pros and cons of one destination, I like real photos of those destinations too. With grey sky, cars, people, with garbage around if there’s garbage – it just makes the photo much more interesting that the pure landscape with no people on it, just because we all know that in most cases that’s not the reality.

    1. I totally agree with Anca! Though my eyes are initially drawn to pretty landscape photos and powerful portraits, I also love and appreciate real capture of the experience. Real snap shots make it relevant and more personal.

  2. On days – and conditions – like that, I really enjoy having my iphone with me. I feel like the Instagram editing functions are actually great for turning washed-out days and scenes into something dramatic (and not too grainy). I know I am a total amateur, but I havent yet figured out the way to replicate the results with a mix of my DSLR and computer editing tools.

    1. That’s true! And I have a suggestion — Trey Ratcliffe from StuckInCustoms.com has Lightroom presets (filters, essentially) you can buy for around $20. I got them a few years ago and they helped my photos in the short term and taught me different ways of editing in the long term.

  3. Thank you for this post! I think there is a lot of pressure for perfect photography, but it’s not always sunny, or other conditions aren’t perfect. I still think these pictures are beautiful. The way you captured the colors of the buildings and that cat (!) was beautiful, perfect lighting or not.

  4. Travel photography is one of my biggest struggles. Maybe it’s the perfectionist in me. Glad I’m not the only one. ๐Ÿ™‚
    I LOVE your photo of the blue house!

  5. I’m no expert, but I don’t think the photos are that bad – I’ve seen worse ๐Ÿ™‚
    But I know the struggle. And I’m definitely not a great photographer.

  6. I’m not a professional, but have been doing SLR photography for 6 years and have done lots of cool workshops, and I think you still got some great shots! Professional photographers usually say that they are lucky if they get 1 useable/sellable shot out of a day’s shoot, so honestly you did great from that perspective. ๐Ÿ™‚ Also, the only “tricks” are, as you mentioned in your post, to shoot for more detailed shots that don’t include sky or just plan to shoot indoors when the skies aren’t pretty. For landscape photography, we basically only shoot in the hour before sunrise and the hour before sunset each day!

    1. Thanks so much! That’s something to remember. The thing is that travel bloggers and Instagrammers are expected to produce, produce, produce high quality content on a regular basis. It’s like we’re constantly being chased!

  7. Ah! I feel as if I have written this post…this is so true. I love taking pictures on my travels. In fact, it’s my primary motive. And it happens so many times that things don’t turn out the way I desired or anticipated. But, photography is STILL magical.

  8. Why would you hire a guide if your main interest is to take good photos of the colorful houses in very specific conditions? What would have been his contribution in that anyway? I don’t get it…

    I know blogging requires a lot of -let’s say- “story telling” in order not only to write a longer article but also to make it sound more real. I admit it often works well in your own posts which I usually enjoy reading. But not this time. Your story doesn’t make any sense to me. I wish your next post is more authentic.

    1. She was on a press trip, which is mentioned in other posts. So the itinerary for the bloggers was set.

      It’s a pretty straight-forward story. She had a hard time taking photos of Old San Juan on her recent trip to Puerto Rico. Sometimes trying to take great photos while travelling can be really frustrating.

      Lesson: some travel days/experiences will be frustrating and not a home run. She wishes she had better pics of this great place to share.

      That’s it.

    2. Thanks for sharing, Julianna, and I appreciate you letting me know. I know not every post is going to be a home run with every reader (and you can’t please everyone all the time).

      I had a guide because this was a press trip. A guided tour of San Juan was part of the trip. Press trips ordinarily are not the best ways to get photos, and the bad weather and light added to that.

      Just one thing — did you really mean to use the word authentic? I think that a post like this is far more authentic than a generic “Old San Juan is so pretty” post. This was my experience, exactly as it happened, which is why it was authentic.

  9. For what it is worth – my pics are usually pretty good and I had a VERY hard time getting good photos there too. Exactly like you said. Narrow streets with too many cars, bad weather/lighting (if it makes you feel any better, shots in sunny weather weren’t much better — the lack of clouds just caused really strong bad back lighting). Extremely hard to capture the charm.

  10. As a mere traveller, rather than travel blogger, I both feel frustrated when the conditions for photography aren’t right and ashamed – shouldn’t I just be taking it all in, living the moment, rather than focussing on the picture? Recently that happened to me in Ihla Grande – it was grey but fine enough for hiking, and chilling. But I was so frustrated not to see it in its best light, literally, and to not be able to photograph it properly (I could just imagine what it would be like, how much better it would be)… I also find that it helps to travel with people who also understand photography and are also into it; because it can require, like you say, changing your itinerary a bit to have the best conditions, and a lot of peopel feel you are mad to do that, just for a good shot. And of course it helps to have someone who is patient when you are trying the 4th angle for the same street… ๐Ÿ˜‰

  11. Sometimes when I travel I forget to take photos all together because I become so distracted by what I am doing and that can be the worst sometimes because then you don’t have photos to share. But yes when you have bad lighting it can be very frustrating. Your photos came out great though! You can always brighten them up by doing a little editing too, that helps =o)


  12. I’ve started to embrace the idea of traveling mainly to eat and take pretty pictures – it definitely changes the way you approach travel, even when you’re doing it strictly for your own enjoyment.

    That said, the photo of the cat is great! I also love the vertical image of the blue building. Playing around in Photoshop could give the others more impact, if you had the time and desire. (I was able to save several blah pictures from a recent trip to Mexico City and just wrote about it on my blog.)

  13. Sometimes, I get a bit bummed out by a trip if I don’t manage to get any nice photos. It’s a bit silly when you think about it, but I love being able to go through beautiful pictures of a place after visiting.

    Recently, I was in Bucharest, and the weather was awful: gray, dark, rainy, and cold. In a way, though, the gloomy weather was a blessing in disguise, since it forced me to focus on things other than the physical appearance of the place (e.g. food, culture, conversations with friends).

  14. Romania is in DIRE need of some underground parking: virtually every beautiful old town I visited in Transylvania was marred by streets and streets of cars parked wherever there was space. It really does hinder your ability to get a good shot.

  15. Narrow streets and bright sunlight can sometimes create really distracting shadows, depending on time of day, of course. Cloudy and/or overcast can be a good time to get photos without those shadows, sort of akin to shooting early in the morning or late afternoon/early evening. I think that’s what you managed to do here, and they look pretty good to me.

  16. I know the feeling of having a bit of bad luck when you’re trying to take photos. Especially when it’s because of the weather, because we literally have no control over that. Maybe it’s different if you’re on a press trip, but I try to take off the pressure of capturing the most stunning photo possible so that it doesn’t drive me crazy. And truthfully, sometimes when they’re not ‘perfect’ they actually look better ๐Ÿ™‚

  17. I totally understand the frustration but I think you did a great job considering the circumstances, you got some really pretty angles and edited them nicely.

  18. As I start to jump into the photography game, I’m definitely finding this. I live in Philadelphia, and cars EVERYWHERE do not do wonders for photography. But I’m trying to embrace it. Travel photographers must have such insane amounts of patience! I am very impressed.

    Aside from the cat picture, I also love the shot of the bright blue building…with the string of lights in front. ๐Ÿ™‚

  19. I’ve been a faithful follower since your first year. I’ve been a Portrait and Wedding photographer for over 45 years. I think you do a Great job at travel photography. You have really improved a lot over the years! I enjoy all your tips and insight. I myself have traveled as a Solo Senior for many years and your comments about landscape and weather conditions, time of day, placement of sun is all right on. Travel photography is a specialty I’m still working on too! Keep up the good info. I have traveled from hostels to luxury and I really like your budget travel advice, don’t forget us budget conscience nomads! Thanks!

  20. If these are the pictures you hate then a) you just be a wizard with editing and/or b) San Juan must be amazingly beautiful! I’m one of those people who sometimes falls into the trap of idealizing the life of a travel blogger; then posts like this remind of how much work it is and I’m grateful for my lower stress trips, infrequent as they are!

  21. True,you just have to stop fighting and take what nature has given you for the day.We cannot control rhe sun,the rain,the clouds,the wind but we can instead use them to our advantage and come up with great results.You also look at you photos and get shocked;like that cat was wow.

  22. Don’t get upset my dear. That happens. Besides this, my husband is a professional photographer, and he always tells me that usually among all the pictures we take, less than 10% is really good. Sometimes we are so excited with the enviroment, that we can’t jugde correctly or analise in detais, and we photograph lots of common things…. and other times, when the enviroment is not so exciting, then we need to do an effort to have a good photos…. and it becomes incredible. But there are days when nothing happens, just because we are not inspired enough, and it is ok.

    1. Yeah, that’s something important to keep in mind. ๐Ÿ™‚ It’s just tough that as a blogger (and Instagrammer) you’re expected to CONSTANTLY produce, produce, produce new and excellent photos from around the world!

  23. Hehe, I know what you mean. But your photos are good anyway and just beautiful because they reflect real life. Without removing cars or getting up for the right weather conditions. Go on like you do, I love your blog! Katrin from ilovetravelling

    1. Its very true that photos enhance any experience or story, but one should realize that more and more people a day are becoming “photographers”. This causes the creativity and competition for photos to be more competitive than ever before, its really difficult nowadays to really stand out among the crowd when so many people are doing the same thing, which in this case is photography.

      1. Well, it depends what your goals are. If you’re doing it for fun, go ahead! If you’re doing it for a career, it’s not only important to be good, it’s also important to be different.

  24. I know what you mean by having photography as high a quality as you can! You’re one of the best and sometimes, it just isn’t your day.

    I met Gary Arndt last year at TBEX and asked him about what to do as I feel more comfortable with my iphone than with a large camera, and he gave me good sound advice.

    The fact is, I’m a writer and sometimes, I get great photography and sometimes, I don’t. I put the fantastic ones up and unless, I have absolutely no choice at all, I leave the shabby ones. Sigh!
    p.s. I’m far better at close ups and still-life than further away lol!

  25. I agree with many of the other people posting…the cat photo totally rocks! This post hit home with me. I recently did a 10-day road trip in Spain, and we had only one day of blue skies.

  26. interesting thoughts. It depends I guess on how long you have in a place and how serious you are about photography, If youre a professional photographer you’re going to have to time yourself relative to best light in day and year terms. Lots of early mornings probably and you’d be able to have less traffic, parking and people depending where you were. Light would be good at that time of day depending on your intentions too. great post kate

  27. Haha we can definitely relate to this experience! Though we are far from being professional photographers, but we are passionate and try to improve in photography. And oh, that feeling to wake up on a cloudy day and then huffing and puffing about all the pics we have taken… where are the colors? And then the crowd, the vivid red / yellow traffic signs / huge cars parking in front of that lovely little house we want to take a picture of… Oh, and reconstruction as these nice old buildings need almost constant recontruction. ๐Ÿ˜€ Life is like that. We try our best. And raindrops on the leaves and on the flowers could be nice for close-ups. At least. Though they do not really tell anything about the city. ๐Ÿ˜€

  28. I was raised in San Juan (though Miami is home now) and being from the Puerto Rican capital I can say the photography gods WERE smiling on you. ๐Ÿ™‚

    Thanks for sharing these images and bringing a smile to my face.

    Happy travels!
    Carl Kruse

  29. I used a film camera on my trip down to the South of England for some of inner-city shots (the Camera was nearly as old as me), but I found it actually quite therapeutic.

    It took away my neediness of, “THIS NEEDS TO BE THE BEST SHOT EVER!”, because I had less control (or idea) of how the photo was going to turn out.

    Some of them turned out really well, too.

    Nice little idea if you find yourself getting stressed out over shots.

  30. I like the one with the blue doors on the pin! But I know what you mean when it comes to bad photography days.

    It’s amazing how much difference the sun makes, the differences between my photos in Germany (which was mostly grey) and sunny Portugal and Spain was astronomical.

    I remember being really sick and tired in Madrid but forcing myself to go to Toledo and literally crying in a square because the weather forecast had promised sun and there was none and my photos weren’t turning out great!

  31. Lovely post! I completely understand the photography issues. The last line just nails it though. I also strongly believe that it is indeed important to take in whatever the country/city has to offer. And I love the last photograph! ๐Ÿ™‚

  32. Photography is a means of connecting with the underlying current in a place or a subject. I think the most compelling photographs focus on an idea or a subject, but a lot of “travel photography” is mostly about pretty colors, etc. Looking too hard can result in not “seeing” at all.

  33. I think we’ve all been there. I certainly have. I did most of my travels with a simple point-and-shoot, and although I got some nice pics out of it, any other weather condition than clear skies had a huge impact on the vividness of the pics. Still, I believe it’s ‘the eye’ of the photographer that comes first, but of course bad luck is bad luck too ๐Ÿ™‚

  34. Sometime I have planned to take a photo of something, but apparently the place was too crowded, or suddenly it was rainning. What you said is true, just lean in and take what it gave me hehe ๐Ÿ˜‰

  35. hahahaha I laughed a lot with this post, Kate! Iยดld like to be a good photographer, but… Buah! The important things are the stories. And, as you have proved, there is a story behind a bad photo, too!

  36. I don’t think its possible to have everything in life. But your photos capture the reality of those places and it’s quite important as a travel blogger for you to feed us the real thing. So bravo Kate, keep up doing what you love most!

  37. Yes, I know that feeling… when I can’t take the photo that was in my mind. When that happens to me I try to change my perspective, and I don’t mean I turn my camera to the other side. It is the perspective in me, I try to let go of what I wish it was to accept what it really looks like and how I can catch that atmosphere that is really there and not the one I so desperately wanted to see because I saw it somewhere or read about it. When I can change from my wanting too hard something that obviously isn’t there to accept what is really around me I usually am positively surprised with the result, sometimes then the photos turn out to be a lot more dramatic.

    Wish you great photo-weather for your next trip!

  38. I’m a newbie in the blogging world, and I can honestly connect with this post. I keep hearing it’s all about “content, content, CONTENT!” But I’m not a professional photographer, so I do the best I can. Your post has inspired me, and your images actually turned out great…probably a lot better than you think! Thanks.

  39. Love your blog. I enjoy your photos and writing. We were very fortunate to have traveled to some beautiful places in Europe. I found the quickest (not the cheapest) way to see places is to go on a cruise.
    The only drawback of a cruise is that 99.99% of the time you only have a few hours to spend at a place. Being a professional photographer that is extremely frustrating. 90% of the time just talking the picture to have it – cannot come back later when the situation or light is better.
    Keep it up

  40. Some really awesome shots in this one. Great work! I really want to visit somewhere like this or Iceland where you get those long sunsets. I great pleasure to see all images.

  41. I feel like this is the story of my life on work trips! I’ve been trying to let go of any expectations I have when it comes to lighting and weather on my trips because I end up disappointed if things don’t work out as planned, but it’s really tough for me to let go of.

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