Unearthing the Personal
Toni Lepeska, the Writer’s Digest 3rd Annual Personal Essay Awards grand-prize winner, discusses the difference between journalism and essay writing, exploring grief, and raising the bar for yourself.
As I speak with Toni Lepeska about her grand-prize win in the Writer’s Digest 3rd Annual Personal Essay Awards, it strikes me by the passion in her voice that this is someone who takes her writing career very seriously. She’s been a professional journalist for 30 years, and she says that her favorite stories to cover have always been about people rising above adversity.
“Those stories, I think they resonate with people because we all have something that challenges us and that maybe we think we cannot beat,” she says. “Those stories can be so inspiring to people.” She recounts a particularly impactful story of a woman who had a facial tumor that led to her being permanently disfigured—but it was her optimistic attitude around her diagnosis and treatment that Lepeska carries with her, years after the interview was conducted. “I just want people to be able to grab a hold of something in a story … and be able to go through their situation and overcome it or to survive it with a more positive way for them [to live] their lives.”
She had been writing about others and their challenges for about 20 years before she lost both of her parents. While dealing with the emotional backlash of grief and loss, she set to the task of cleaning out their home, which took several years. “I couldn’t bear to throw away or give away much of anything. Everything had enormous feeling attached to it … even though I’d be crying, it was very healing.”
The deeper she explored these feelings, the more she felt the call to write about them. She says, “I don’t think writers can resist emotional journeys—especially their own … I was compelled to tell my own stories for personal reasons, but I also felt compelled to help other people with the many facets of grief and loss through storytelling. I’m still in the journalism world! But that’s how I transitioned into learning about how to tell a personal story.”
This sent her on a quest to write a memoir that documents that experience. Very early on in the writing process, she says that a literary agent recommended she read Eat, Pray, Love by Elizabeth Gilbert. “I just was riveted by that memoir because of her voice. It’s so conversational! It was almost as though she was sitting on the other side of my coffee cup telling me her story. I kept thinking, Gosh, this sounds so familiar. That’s when it dawned on me that I write long emails to my friends that had a similar tone. I realized that I had been stiff in my telling personal stories [for publication].”
She changed her approach to storytelling and started focusing more on personal essays. A subscriber of Writer’s Digest, she set about entering the personal essay competition—and placed as honorable mention the first two years. “As delighted as I was to be receive an honorable mention, I was wondering, What do I need to do
to place?”
At the same time, she began wondering if she should enact a drastic change to her memoir—replace the past tense with present. “But was I correct? That was my question. I had that doubt that we all—all writers—carry around with them.”
She decided to try it out on an essay she titled “Five Nights in Milford” and enter that into the Writer’s Digest Personal Essay Awards. “I thought that if I could place in the Writer’s Digest contest … it would be an affirmation that I could do it, I could write in the present tense, I could write in scenes. So, winning this essay contest was really a big breakthrough for me.”
This excerpt demonstrates this journey of experimenting with her writing and finding a solid voice:
I am alone, more than 1,500 miles away from home, in an unfinished basement illuminated by a single shop light to save what’s left of my family. My grandfather built this Cape Cod style house in Milford, Conn., 70 years ago. My daddy grew up in it, and my uncle brought his bride to this home. They are all dead now. Everyone who ever lived in this house is dead, but my uncle’s hoard is here. It is as tall as I am and as wide as an entire basement wall. The mound feels like a single, impenetrable, impossible mass. It’s the last of his accumulated possessions. I know it hides gold. Emotional gold. The essence of my family.
It’s all that is left of them.
With hands on my waist and elbows cocked out, I look like I’m in command, but I’m not sure where to begin.
How in the world am I going to do this?
Hoards seem to be a genetic component of my family, but I’ve never had to dismantle one this massive to find the stuff worth keeping. It puzzles me that despite his attachment to stuff, Uncle Karl did not sign a will for the distribution of his property. And my aunt, his wife, who survived him by six years, was not medically fit to make a will the courts would accept.
That means her family is inheriting everything. People I barely know.
I asked one thing of them. Allow me to go through my family’s things.
They gave me five nights.
Lepeska’s winnings include $2,500 in cash, a paid trip to the Writer’s Digest Annual Conference (including a coveted Pitch Slam slot), and more.
So, what’s next for her? “I’m picking that [memoir] back up this year! I want to show people through my story that they can go through grief and loss and lose a sense of safety and security, try to resurrect it and get no results for some of the things they try, and yet find beauty in life again. That there’s hope for restoration. The grief is hard, but it’s also the pathway to a sense of healing.”
And for all aspiring essayists out there, she wants to leave you with this: “Keep learning. Writing can be a gift, but it is definitely a skill. Believe in your ability to be able to learn even when your head is spinning and even when you don’t seem to be getting it. … I could have given up, but I decided there was something else for me to learn and apply. … You just need to find the right resources, find the right teacher, and find what works for you.”

Since obtaining her MFA in fiction, Moriah Richard has worked with over 100 authors to help them achieve their publication dreams. As the managing editor of Writer’s Digest magazine, she spearheads the world-building column Building Better Worlds, a 2023 Eddie & Ozzie Award winner. She also runs the Flash Fiction February Challenge on the WD blog, encouraging writers to pen one microstory a day over the course of the month and share their work with other participants. As a reader, Moriah is most interested in horror, fantasy, and romance, although she will read just about anything with a great hook.
Learn more about Moriah on her personal website.