In 2022, Katie Boland began to compile a mental list of all the mistakes she’s made—getting married at 21 to a born-again Christian, only to get divorced six months later, falling in love with several different con men, being a surprise alcoholic— and a myriad of other sticky situations in both her career and personal life.
But during what she describes as an extreme personal low point, her mindset shifted. “I realized that actually the mistakes were the greatest catalysts for growth, and that I have learned so, so much from each choice that I made,” she says, deciding that if she could grow from her mistakes, she could help others struggling with the same things, especially younger women.
“I love Dear Sugar, I love Ask Polly, but everything felt like it was for an older demographic. I felt like there was such a vacuum, particularly for young female artists,” she says. “Where do you go to get advice? Where do you go to get help from someone who’s seen it all? Where is the advice column for like a person like me?”
Now, that column is finally here.
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In All The Mistakes I’ve Made, Katie’s new, unfiltered advice column with SheDoesTheCity, the award-winning actress, writer, and director is ready to recount all of her cringe-worthy moments and colossal fuckups as she answers your questions about life, love, and career.
“There’s a litany of mistakes I made that are going to be amazing fodder for the column,” Katie says. “If I’m going to ask people to do the brave thing of putting themselves out there…I need to be doubly as brave and be like, This is how I fucked up, or This is something I wish I didn’t do, but here’s how it turned out and that’s why it was okay.”
Equal parts funny, compassionate, and insightful, All The Mistakes I’ve Made will be filled with Katie’s brutally honest advice, stories of the mistakes that shaped her, and reflections on how they ultimately put her on the right path, even if it’s a different path than the one she imagined.
Katie’s dream, from age three, was always to be an actress—a famous one. She had a robust career as a child actor and into adulthood, with more than 85 credits to her name, including roles in The Master, Reign, and Five Days at Memorial.
But after years spent in audition rooms, waiting to land the next role, she began to face some difficult realities about her lifelong dream. “There was only so much control I would have over my own destiny as an actress. Other people would have to choose me,” she says.
So, she turned to writing, a decision that opened the door to an array of creative projects that would shape the next chapter of her career. She began writing personal essays, which she adapted into a Hulu web series called Long Story Short. She published a collection of short stories, began writing for television and film, and went on to direct several shorts and feature films.
“I never saw myself being a director. I never saw myself being a screenwriter. I didn’t think I would write an advice column. I didn’t think I would write a book. I thought I would just be an actress. By letting that go and having an open mind, all of these opportunities that became my life are available to me.”
In 2022, Katie released her debut feature, We’re All In This Together— a dark comedy film which she wrote, directed, and starred in as twins. The story explores alcoholism through the lens of a dysfunctional family, as twin sisters Finn and Nicki are forced to reunite while they wait for their mother to rise from a coma.
It was an ambitious undertaking for Katie, who looks back on the film as one of the most rewarding projects of her career. “I was given the opportunity to wear so many hats, and it’s given me more confidence and competence to go in the direction of my dreams.”
That direction is full steam ahead, with no shortage of creative projects in the works. She’s releasing a podcast about women’s health, directing another film for Lifetime, writing a memoir for Sutherland House Books, and working on her next two original features. While she loves wearing many creative hats, writing is what Katie describes as her “truest voice”.
“The column is a return to the work that I like most, which is personal essay writing,” she says. “SheDoesTheCity gave me my first-ever job as a writer.”
Katie published her first personal essay with SheDoesTheCity in 2017— a powerful piece about her experience with anti-depressants. “That article got such a big response that I felt like, oh, maybe I’m able to connect with people here. To come back now and to try to help other people and also talk about the mistakes I’ve made in my relatively long career… it’s really full circle to be back here.”
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She believes All The Mistakes I’ve Made will fulfill her dream as an artist—being able to use her voice to help people.
“I have a lot on the go. But when people ask me what I care most about, I say All The Mistakes I’ve Made. All I truly want to do is help people, specifically younger women and non-binary people who are struggling,” she says. “I hope it reaches people. I hope it helps people. I hope people can laugh at the mistakes I’ve made…I hope I get to keep living and keep making mistakes and keep writing about them.”
We can’t wait to see what Katie’s future holds, mistakes and all.
If you’re looking for advice, about life, love, friendships, career, or anything else, submit your questions for Katie here. Stay tuned to SheDoesTheCity’s website and socials for the first edition of All The Mistakes I’ve Made, coming soon.
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