We’re looking forward to introducing you to Kaitlin Oster. Check out our conversation below.
Good morning Kaitlin, it’s such a great way to kick off the day – I think our readers will love hearing your stories, experiences and about how you think about life and work. Let’s jump right in? What do the first 90 minutes of your day look like?
I’m an early bird against my will and I have to wake up before dawn four days a week at the moment. I hate alarms, so I set my coffee maker to start brewing at 5 AM to ensure that I wake up to the smell of coffee before the sound of a bell at 5:30. Was this smart? Not really because I now always wake up to the smell of food. I then walk my dogs about a mile because they need exercise too and I live in an apartment, so I start drinking coffee far earlier than I think most doctors would recommend and wander around for about 45 minutes outside, less if it’s raining (the big dog hates rain). Once back inside, I do my Morning Pages. It’s admittedly one of the few steps of the Artist’s Way that I regularly follow; I’ve missed about ten days since January of this year. I write three pages by-hand, pull a tarot card or three for the day, and go to work.
Can you briefly introduce yourself and share what makes you or your brand unique?
My name is Kaitlin Oster and I’m a writer, currently coming up on my statute of limitations of the saying, “It takes ten years to become an overnight success.” I’m the author of the Letters to Loretta Series, a 35-week long narrative World War 2 retelling about my grandparents’ love story while my grandpa was a prisoner of war in Nazi Germany.
I work closely with Corrine Ashley: producer, manager, and overall film industry chameleon. Corrine and I go way back to the days of throwing punches on a karate mat in elementary school, and I am very aware of my good fortune to be represented by not only one of my oldest friends, but someone I would undoubtedly trust in a fight.
My current industry pursuits wouldn’t have come to fruition without Corrine and her gleaming integrity, honesty, work ethic, and overall good-person-ness. We are actively uniting other likeminded creatives and amplifying voices that may be underrepresented or otherwise overlooked.
Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What part of you has served its purpose and must now be released?
I have only recently reconciled with the fact that I cannot do everything myself. I think the flavor of trauma is rooted in unsavory childhood experiences that bled into my 20s. Now, in my 30s, in a healthy relationship, doing what I am meant to be doing, I’ve learned to take a backseat when needed. Hustle culture, early risers (me but not because I want to be), and everything becoming a life hack of some sort has conditioned a lot of us to think we need to either know how to do everything, or that no one can do things like we can. My needs for control were inherited via survival and have been replaced (mostly) with an allowance of nourishment from my community and loved ones.
What did suffering teach you that success never could?
I feel like I’m about to veer hard left here, but I actually think these two words are more related than we give credit. Both require us to reconcile internally if we ever want to make it out alive. I think that you need to be just as prepared to accept low points as you need to be ready to accept success. Both of these things can be devastating if you’re not ready to stand on your own two feet. They differ, obviously, in that you do not need to suffer in order to create meaning, or to create something successful. Paraphrased by David Lynch, but one of my favorite things I ever heard him say, because I limited my writing time to when I was feeling low for years and created a sort of Pavlov’s Dog complex about it. Then, with time, I found myself—maybe unconsciously—seeking out pain. I became addicted to suffering because I liked the satisfaction of creating art. I’m grateful to have broken myself out of that pattern.
Sure, so let’s go deeper into your values and how you think. What’s a belief or project you’re committed to, no matter how long it takes?
Getting my World War 2 film, Jamaica Station, made. And made right. It is, by nature, a big budget movie, but the story is so important, and not just because it’s based on my own grandfather. There are so many complex layers to his journey—from being the youngest son to a German family in New York, to dropping bombs in Germany at 23, to becoming a prisoner of war at the hands of Nazis. The film overall is a study on humanity and love, the importance of art and the written word, how we are capable of enduring immense suffering, and how war itself has become an unfortunate part of the human experience.
Thank you so much for all of your openness so far. Maybe we can close with a future oriented question. If you laid down your name, role, and possessions—what would remain?
A really good story.
Contact Info:
- Website: https://www.kaitlinoster.com
- Instagram: roller_koster
- Linkedin: https://linkedin.com/in/kaitlinoster
- Other: https://linktr.ee/kaitlinoster
