We caught up with the brilliant and insightful Yesenia Rosado a few weeks ago and have shared our conversation below.

Yesenia, thanks for joining us, excited to have you contributing your stories and insights. Can you talk to us about how you learned to do what you do?

I’ve loved photography since high school back when I was developing film in the darkroom and praying I didn’t mess up the roll. My subjects were just my two dogs. That’s really where everything started for me. I fell in love with the process, with storytelling, and with the feeling of freezing a moment that would never happen again. When I transitioned into the digital world, I brought that same curiosity with me.

But honestly? I learned most of what I know through what I lovingly call YouTube University. I was obsessed with understanding every single part of photography; the gear, the editing, lighting, posing, composition, all of it. I’d shoot all day, then stay up way too late watching tutorials, studying other photographers’ work, and practicing until things finally clicked. I was eager, hungry, and honestly just really determined to get better.

If I could speed up my learning process, I would’ve invested earlier in two things:

Hands-on mentorship. Having someone in the industry show me the ropes would’ve trimmed years off my trial-and-error phase.

Real practice with real people instead of waiting for “the perfect moment.” Every session, every wedding, every family shoot taught me more than any tutorial ever could.

The skills that were most essential for me were definitely understanding lighting, communicating with clients, and learning how to make people feel comfortable in front of the camera. You can own the best gear in the world, but if you don’t know how to work with light or how to connect with people, your photos won’t translate the way you want them to. Being a wedding and lifestyle photographer is equal parts technical skill and emotional intelligence.

As for obstacles time, confidence, and comparison were my biggest ones. I was juggling life, work, and learning, so it took me longer because I had to teach myself everything. There were moments when I doubted if I was good enough or if I belonged in the industry. And like most creatives, I had that phase where I kept comparing my work to everyone else’s. Once I learned to stay in my own lane, trust my eye, and give myself grace to grow, things shifted.

Becoming the photographer I am today took patience, a lot of self-teaching, and so much trial and error but every part of the journey shaped how I show up for my couples and families now.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I’ve honestly had a camera in my hand for as long as I can remember. My love for photography started the moment I watched my dad use his old Polaroid to take photos of his job in the city’s sewage system. Definitely not the most glamorous images, but I was obsessed with the process watching a moment turn into something you could hold in your hand within seconds. That feeling stayed with me. And of course, being me, I would sneak his camera whenever he wasn’t looking and take photos of anything around the house.

High school is where everything really clicked for me. The darkroom became my little sanctuary. There was something about the slower, intentional process, the smell of the chemicals, the anticipation, the quiet that made me fall in love with photography in a way I didn’t even fully understand at the time. When technology shifted and the digital world took over, I found myself at Circuit City buying a tiny point-and-shoot, just hungry to keep creating. Eventually I upgraded to my first DSLR, a Nikon D750, and that’s when everything started to unfold.

My friends and family were so supportive, which gave me the courage to say yes when a friend of a friend asked me to photograph their wedding. It was a huge learning experience the kind of day where you walk in nervous, learn on the fly, and walk out knowing you were made for this. From there, I naturally fell into wedding photography. As cheesy as it sounds, I fell in love with capturing love. Weddings, engagements, families. I couldn’t get enough of it.

Today, I’m a wedding and lifestyle photographer based in Connecticut, and what I’m most proud of is the relationships I’ve built. My clients don’t just hire me for one moment they invite me back into their lives for all the moments: proposals, engagements, weddings, pregnancies, babies, milestones. Being trusted to document someone’s story over and over again is the highest honor.

What sets me apart is connection. I’m not just showing up with a camera. I’m showing up as someone who wants your photos to feel like you natural, warm, joyful, and true to the moment. I guide my couples through the experience so they feel comfortable, confident, and taken care of. Whether it’s navigating unpredictable weather, helping with timelines, calming nerves, or creating space for candid emotion, I’m there for the whole experience, not just the photos.

At the end of the day, the biggest thing I want people to know about my work is this: I care deeply about preserving your story exactly as it is. Your love, your people, your memories that’s the heart of what I do. And getting to be a small part of so many beautiful lives is something I’ll never take for granted.

What’s the most rewarding aspect of being a creative in your experience?

For me, the most rewarding part of being an artist is the connection. I don’t think I realized how deeply this work would impact me until I started meeting couples and families who trusted me with their biggest moments. Yes, I love creating beautiful images, but what fills me up the most is the relationship behind the lens the way two people let me into their world, their story, their quirks, their quiet moments.

Calling myself an artist still feels wild sometimes, but I’ve learned that artistry isn’t just about the photos…it’s about how you make people feel when you’re capturing them. It’s the comfort, the trust, the laughter, and the little in-between moments most people don’t even notice. Being invited into that space and then watching those images become memories they’ll hold onto for life that’s the part that stays with me.

That connection is the heartbeat of my work, and truly the most rewarding part of what I do.

Have you ever had to pivot?

One of the biggest pivots I’ve ever had to make both in life and in my business happened during COVID. Before the pandemic, I was hyperfocused on “success” in a very numbers-driven way. I had this idea in my head that to be a real wedding photographer, I needed to hit a certain amount of weddings a year. I chased that number so hard. I tied my worth, my growth, and my craft to booking more and more.

Then the world shut down, and it humbled me in a way I never saw coming.

Everything went quiet. Dates were cancelling, postponing, or disappearing entirely. The March 2020 wedding that was supposed to kick off my season gone. And suddenly I was sitting with this stillness I didn’t ask for, in a world that felt heavy and uncertain. It forced me to rethink everything: how I viewed my business, why I loved photography in the first place, and how I wanted to show up for people once the world reopened.

I realized that weddings aren’t about quantity. They’re about human connection, presence, emotion, and the responsibility we have as photographers to document someone’s most meaningful moments even in chaos.

My first wedding back during that time ended up being one of the most beautiful experiences of my career. My couple decided to pivot too. They created the sweetest, safest mini ceremony just 10 people, outdoors, spaced out, masked, the whole thing. Saint Clements Castle was gracious enough to still let them host the ceremony on their grounds. And even in the middle of all that fear and unknown, their love felt like something straight out of a movie.

That day changed me. It reminded me that success isn’t a number. It’s impact. It’s trust. It’s being invited into a moment when the world feels shaky, and still showing up with intention and heart.

Pivoting during COVID didn’t just reshape my business it reshaped the way I see my couples, my craft, and the privilege of documenting real life as it unfolds.

Contact Info:

• Website: https://www.jessra.com
• Instagram: @jessra_photos

Image Credits

Jessra Photography