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Oops, Daisies, and Dreams: Kathy Osgood of Little Bear Photography

February 4, 2026 by Liz SanFilippo Hall

We might talk a lot about writing on Oops and Daisies, but, as the saying goes, “a picture is worth a thousand words.” A beautiful photograph is a work of art and an act of creativity in and of itself, but those photographs wouldn’t be possible without creative-minded individuals behind them, like Kathy Osgood of Little Bear Photography. Here Kathy, who helped me update my headshots and photos when I relaunched the blog back in the fall, shares more about her creative life and approach to photography. 

Affiliate links included. 

Please introduce yourself and share a bit of background about you and your creative life. 

My name is Kathy Osgood, and I’ve been a photographer for 11 years. My degree is in advertising, and I have years of experience working in web and graphic design. I enjoy gardening, baking, and watercolors in my spare time. I have two sons, two cats, a dog, and a wonderful husband. 

Do you have any favorite creators? Who has inspired you? 

I’m definitely inspired by my favorite books I read as a child: LM Montgomery in particular was one of my favorite authors. Her books feel like the most magical childhood. And, of course, Ann Geddes was my original photography inspiration when I was younger. She had such a whimsical style that really resonated with me and inspired me to have more fun. 

photo by Little Bear Photography

How long have you been a photographer? Tell us a bit about your journey into starting your business. 

I’ve been a professional photographer for 11 years, starting not long after the birth of my second son. I was looking for a job that would give me flexibility to work around my kids’ schedules while still allowing me to be creative.

What sorts of ‘oops’ (or hiccups) have you had on your creative journey, and how did you overcome them? 

I think the most important lesson I’ve learned as a business owner is to be less worried about what other photographers are doing and more focused on how to serve my clients to the best of my abilities. It’s a crowded field, and it can be easy to stress out about that, but if you focus on making your clients happy and giving them a great experience, things fall into place. 

What is the #1 piece of advice you’d give to someone who is just starting with photography? 

Worry less about getting fancy equipment and focus more on the basics – light, composition, and storytelling. 

What projects are you working on now? (If you can share!) 

I’m focusing more on branding photography and authentic storytelling. With the rise of AI, I find myself drawn more to artwork that feels genuine and sincere and flawed. Work that’s less polished and perfect, but has more emotion and vulnerability. 

Anything else you’d like to share about you and/or your creative life?  

I just hope people know that their memories and families are precious, and they deserve to be photographed at all stages of life! Don’t wait for the perfect time, or weight, or body shape. Time is a thief, and everyone deserves to have beautiful photographs they’re proud of. 

Find Kathy online 

Instagram
Website: Little Bear Photography

***

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Filed Under: Interviews with Creative Moms, Work From Home Tagged With: art, creative moms, creativity, interview, interviews with creative moms, photography

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authorlizsanfilippohall

Multi-genre author. 📚BECOMING CHARLOTTE CORDAY, a YA historical fantasy coming 4/27/2027 from Apprentice House Press

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