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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 spring 2027 from Apprentice House Press

Bear with me! I do plan to talk about my forthcomi Bear with me! I do plan to talk about my forthcoming YA historical fantasy, but putting something out into the world that’s only been “mine” so far? It’s hard! This is why I talk about mindset and writing so much — your mindset affects your writing… and apparently your publicity and marketing, too. #WritingLife #HistoricalFantasy #BookLife #Mindset
What can I say… I recommend a lot of books 🤣 What can I say… I recommend a lot of books 🤣#ReaderForLife #AmReading
After a fun and lovely huge family vacay at the be After a fun and lovely huge family vacay at the beginning of April, I hit the ground running. There are a LOT of things currently in the works, not just my forthcoming YA historical fantasy. Here are just some of the things I was up to in April:🌸 Wrapped up my in-person picture book writing workshop… and I’ve been getting requests for an online version, so stay tuned!🌸 Ghostwriting projects for my clients, including writing about financial literacy, brand development, and construction.🌸 Shared essays about topics like turning off your inner editor to why your writing process is a garden over on my Substack, Where Daisies Grow🌸 Held my Creative Writing Accountability Club every Thursday morning (it’s free! If you want in, let me know)🌸 Coached some of my clients so they could finish their writing projects. 🌸 Dove headfirst into developmental edits of my New Adult Contemporary. I know, I know, I said I’d let this marinate a bit, but this story doesn’t want to wait.🌸Reached out to some fellow authors about blurbing my Young Adult Historical Fantasy (a round of edits is happening in May!)🌸 Scheduled a May writing workshop about building a sustainable writing routine that works for your busy life. Hit me up if you want the details.🌸Launched my first printed guided journal full of coloring pages, motivation, and writing prompts for moms who want to cultivate a writing practice. Head on over to my bio for a link. What do you want to hear more about? Lots of messy creativity is happening around here, and I love sharing peeks into my process over on Substack and Instagram.#MomLife #WritingJourney #AuthorsOfInsta
I clearly have a wide taste in books. Don’t be s I clearly have a wide taste in books. Don’t be surprised if every month looks something like this…Mystery/literary HorrorMagic/fantasyTearjerker Existential Rom-comAnd I enjoyed them all!#bookstagram #AuthorsOfInstagram #BooksGalore @jpleeauthor
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Ohhh my goodness, my editor totally made my MONTH Ohhh my goodness, my editor totally made my MONTH when she shared why she wants to publish my Young Adult Historical Fantasy about Charlotte Corday. Pinch me! “I was immediately pulled into the magic and fantasy elements of the story. I really loved how you connected real history to the plot without it ever feeling like I was reading something overly educational or dense. I’m honestly not much of a history person, but your writing made me curious enough to want to look into some of the historical elements more after I finished reading. I also grew up loving fantasy and magic-focused stories like Harry Potter and Percy Jackson & the Olympians, so that part really resonated with me.”#AuthorsOfInstagram #HistoricalFantasy #WritingCommunity #TimeTravel @apprenticehousepress
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I spy something new I’ve created 🧐😉 If yo I spy something new I’ve created 🧐😉If you want to see it firsthand, hop on by the Wheaton Library Local Author Fest on 4/25 between 1 and 4pm!Otherwise, you’ll have to wait until next week for the full reveal 😊#WritingLife #PictureBook #AuthorsOfInstagram
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