Meet Kaitlin Oster

Alright – so today we’ve got the honor of introducing you to Kaitlin Oster. We think you’ll enjoy our conversation, we’ve shared it below.

Hi Kaitlin , thank you so much for opening up with us about some important, but sometimes personal topics. One that really matters to us is overcoming Imposter Syndrome because we’ve seen how so many people are held back in life because of this and so we’d really appreciate hearing about how you overcame Imposter Syndrome.

My imposter syndrome came to be when the person I had to impress was myself and not my parents. The household I grew up in surrounded greatly around performance-based praise and as a result I developed the need to live up to other people’s expectations and never learned how to fully live up to my own. That wall didn’t entirely start to crack until 2022, three years after I wrote a World War 2 narrative called Jamaica Station, and just a year after I serialized the book for my own personal website. I was invited to have a meeting with the editor-in-chief of Sandboxx News, who praised my series and asked if I’d be interested in contributing the story as a weekly Friday feature for their mass publication. I remember sitting at the end of my bed after the meeting, full of joy that I’d sold my writing, and at the same time I could identify this weird emptiness that sat alongside of me. It was imposter syndrome, telling me that my work wasn’t good enough to be a feature.
I reached out to some friends, who all expressed the same joy that I initially felt and that’s where my mentality started to change. My friends don’t lie to me; Part of me was lying to myself. I ignored the imposter voice and I’m glad I did, because the first series I’d ever written ran for 35 consecutive weeks. An important story both to myself and to the world of history was immortalized as well as impactful for readers, and I was responsible for it. Imposter syndrome still knocks on my door but I do what any millennial does when someone knocks on the door – ignore it.

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

I am in constant pursuit of the story and amplifying the voices that tell them. I think that the circumstances I’ve encountered throughout my life have led me on this path because I’ve always been either encouraged to believe that there is meaning in everything. I didn’t find my true writing voice until my 20s when I had no choice. I found myself in such a deep depression after losing my mom and feeling this enormous sense of isolation that I was overcome with this need to write. Write or die. A little morbid, yes, but nothing else seemed to remedy the pain, and nothing else was in my control other than what was inside of me. So I wrote. I wrote about my mom, her alcoholism, my body image, my fears and my dreams – only to be met with community, understanding, and people who felt a little less alone because they could relate to my experiences even if they weren’t identical. It’s inspired me to become a professor and help students identify their unique voices in addition to hosting a free grief group in my community where peers can share their experiences in a judgement-free environment.
Today, I’d say I chase more stories that aren’t just my own. Most recently, and for the last five years, I’ve been nose-deep into a World War 2 narrative that was inspired by and mostly based on my grandparents’ love letters from 1936-45. My journey with the series began in 2019 after I lost my grandfather; my grandmother died in 2007. He was my maternal grandfather, and having already lost my own mother in 2011, I wanted to immerse myself in love instead of falling into the extreme depression I experienced eight years earlier. So I pulled about 120 letters from a box that my grandmother kept meticulously organized, and with the help of their voices, research at the Mighty 8th Air Force Museum outside of Savannah, a narrative edge, and scouring some Red Cross documents, I created a story for people who could no longer tell their own.
This, of course, became the Letters to Loretta Series, based on Jamaica Station the book, and most recently the screenplay of the same name. Since its publication, I have been in contact with the Mighty 8th and will be present from January 10th-12th, 2025 to talk about the series, human resolve, the power of love, and the importance of writing. We plan to have many of the letters on display in the art exhibit on-site in Georgia, and in addition to the display, I spent this past winter transcribing every letter by hand in chronological order with the hope of having the material published.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

I am just going to create a list:
1. The biggest hurdle of why we don’t pursue something is often ourselves. Whether imposter syndrome, lack of confidence, fear of rejection… Much of life is learned by doing, so if you enjoy the thing you want to pursue, go for it, even if you’re bad at it when you first begin.
2. If you know why you want to pursue something, worry less about the how you’ll find success doing it. I think a lot of creatives are successful because as viewers, we can see the heart and soul – the genuine voice – that goes into their expression.
3. No matter how alone you think you are, you aren’t. I say it as someone who’s struggled with (and continues to struggle from time to time) depression. I try and remind myself of the people in 2013 who told me I helped them feel less alone. Even if someone isn’t experiencing the exact same thing, someone can relate.

How can folks who want to work with you connect?

I am always open to genuine creative collaboration. My skillsets are heavily into writing and editing, but I always love a good story and also have experience as a professor, speaking in public, and researching topics. I am a freelance creative consultant as well as a narrative writer, academic, and screenwriter.

Contact Info:

• Website: https://www.kaitlinoster.com
• Instagram: @roller_kosters
• Linkedin: https://linkedin.com/in/kaitlinoster
• Youtube: https://www.youtube.com/watch?v=xtKA4GgzkLY
• Other: https://www.sandboxx.us/?s=kaitlin+oster