Failures and Successes — hudson valley photographer

This is my 11th (12th??) year in business. And each year, I get just a little bit better at running a business : ) (I mean, not so good that I actually know off the top of my head how many years I’ve been in business, lol, but … well … a BIT better.) My fellow working artists out there no doubt understand exactly where I’m coming from when I say that one of the all-time biggest challenges of being a professional photographer is that you’re only actually photographing things like 20% of the time. Really, the majority of the time you’re a scheduler, planner, marketer, book keeper, web designer, etc. You’re a business owner.


I started off as a good photographer … and a horrible, clueless business owner. I’m now an ok business owner (I’m happy to say, though, that I’m a great photographer!) I should be better at the business ends of things by now; but that’s ok. I’m ok with where I’m at. I’ve never been super fast to change or grow with anything I do; I’m more of a slow and steady sort of person. I’ve learned that as long as I see steady growth, I’m happy with that.

What I love most about my business is that I get to provide a service that makes people happy. That is really, really, really fulfilling and it makes the struggle to learn how to be a better businesswoman even more worthwhile. I happen to really love people … and getting to know clients over the years has been my all-time favorite part of this crazy ride. And the added bonus is that as clients’ comfort levels with me as a person grow over the years, their photos just get better and better. I love that!

I appreciate that my clients trust me. They invite me into their homes. They trust me to photograph them on the most important day of their lives … their wedding day! They allow me to spend time with their most precious possessions of all — their little ones. I appreciate that trust. And in return, I’ve always been very open about how things are run around here. So with that in mind, I thought I’d share some of what I think are my failures and successes from this past year : )



SUCCESS: Weddings! — A while back, I “retired” from weddings. I had this strange love/hate relationship with them. I LOVED shooting them. But I’d get so anxious about all the things that could go wrong at a wedding, that I found myself stressed all the time. I shot weddings for about five years with a huge cloud of panic hanging above my head. SO much panic for nothing since I never even came close to messing up a wedding! I think it’s really just a testament to how much I want to give people beautiful photos! (And perhaps a little related to my being a perfectionist ; )) But when I “retired,” I missed it. Strange, huh? So back in they came a few years back. But I decided to only accept a few per year, and to actively focus on overcoming my wedding-related anxieties. This year, I’m happy to say that I enjoyed every single one of the weddings I shot. And I mean, I ENJOYED not feeling anxious … but rather, simply being in awe of all the beauty and love I was getting to capture. I can’t wait for my 2019 weddings!

FAILURE: Life Lessons with Little People — Aw, man. I really had big plans for this little project for 2018. It’s a really, really fun project for me to work on. I love hearing what little ones have to say. And people tell me that they love reading the posts that I put up for this project. Winter is always my slowest time, and I often set my goals for the year during that period, which is what I did for LLWLP this year. But then the moment the busier season picked up, I accidentally dropped the ball on this project. It’s not a project that I want to end, but it is currently shelved … just until I’m ready to do it justice : )

SUCCESS: Repeat clients — My photography business is my only income. I suppose a growth in income should be the thing that makes me most satisfied with my business; but honestly, it’s not. Repeat business is what makes me the happiest. It’s not lost on me how many photographers my clients can choose from. I know there are so many amazing family and wedding photographers in the Hudson Valley and in Delaware. So when people choose me year after year, I can’t even begin to explain how much that touches my heart. This year I got to work with so many repeat clients … so that truly feels like my biggest success of all.

FAILURE: Blogging — I have good intentions for my blog every year. Actually, when I sit down and lay out what my year is going to look like every January, blogging is at the top of my to-do list. And yet, this year, despite knowing how important it is to blog, I really dropped the blog ball. Blogging and videos are on my list for 2019. (Ugh, videos. I’m petrified/determined/excited/nervous to start sharing some videos!) I’m determined to become one of those people that is truly, truly regular with content. I know other photographers and bloggers who do it. So it can be done!

SUCCESS: Equipment upgrade — I got a new main camera this year … which is, in my mind, a double success. 1.) The features truly are better on this camera, particularly for weddings. It’s made a huge difference in how I’m able to shoot. So, that’s, of course, a major success. 2.) But I’m more proud of the fact that I upgraded only when I truly needed to upgrade. My main shooting camera was old. She was still working great, though … but kind of like a car with 300,000 miles on it. Even if it’s running, you know the end is in sight. (haha, that’s my car right now!) I don’t believe in spending tons of money on equipment in order to be a good photographer. So I’m proud that I stuck to my guns and didn’t upgrade just for the sake of upgrading. I waited until it was necessary.

SUCCESS: Digital files — I debated for a long while before switching over to offering just the digital files (clients can also order prints from my pro lab straight out of the galleries I provide them with, too, if they wish). My biggest fear was that clients would take their files over to their local drug store and get really poor prints made up and then feel disappointed with their photos. I never want people to be disappointed with anything I photograph for them! But as it turns out, my fears were all for nothing. Clients continue to share with me snapshots of their wall galleries that they make from their digital files from labs like and … and they’re absolutely beautiful. I see their canvas wraps, their beautiful cards, their photo books … and I’m beyond thrilled that I’ve provided them with the means of really getting so, so, so much out of their photo session. I’ve gone from being hesitant about offering the files, to being incredibly excited to see what clients will do with their files!

FAILURE: Professional development — I’m running on E right now, creatively speaking. This is a familiar feeling … particularly after the busy fall season. But it’s just plain old a sign that I didn’t properly look after my creative tank. It HAS to be refilled through personal projects, trips to museums, inspiring books, etc. I’ll put it right back on the top of my list for 2019.

SUCCESS: Extended family shoots — I didn’t really mean to become an extended family photographer … but this summer, that’s exactly what I became! The Hudson Valley region is a vacation spot for many families; some of whom contacted me for extended family shoots. I was nervous at first because I worried that we wouldn’t be able to capture photos in my typical way (not too stuffy or overly posed). But as it turned out, I really, really loved it. The thing that helped most was encouraging everyone to have an activity they could do together during their shoot. This allowed for natural and fun photos of the family members interacting together. This is something I’m going to continue to offer! If you think you might want to include grandparents and more in your next session, let me know. We can talk about the way to make it a huge success for your family.

There it is! My list. I feels good to think back on the accomplishments … and it even feels good to acknowledge the areas where I need to improve. I’m excited to see what 2019 brings! I’ve got two weeks left for this year, and I’m going to be spending that time mulling over the direction(s) I want my business to go in next year. Then come January, new goals will be set!

Thanks for reading along : ) And if I worked with you this year, thank you for being a part of my little business. It means the world to me : )


Kate Callahan is an on-location photographer who LOVES to capture authentic memories for families. She’s available for weddings, senior photos, child photo sessions, and family photography. Kate works with clients throughout the Hudson Valley, NYC,  Delaware (and the tri-state area), and beyond. She also writes motivational books for photographers. Find them at Dear Female Photographer.

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