From Rock Bottom to Global Beauty Brand: How Jen Harper Turned Generational Trauma into Indigenous Power

I’m going to be honest—before I sat down with Jen Harper, I thought I understood what "resilience" meant. We hear that word thrown around a lot these days, especially on social media. It becomes this buzzword for "just keep going." But after listening to Jen, the visionary founder of Cheekbone Beauty, I realized I had only scratched the surface.

There were moments in this interview where I literally had to hold my breath. Jen didn't just tell me about building a business; she walked me through the darkest corners of abandonment, addiction, and the heavy, invisible weight of generational trauma. And then, she showed me how she lit a match in that darkness to create something beautiful.

We need to talk about the things we inherit from our parents—both the pain and the power. Jen’s story is a masterclass in taking the "messy" parts of our history, the parts we usually try to hide, and turning them into our greatest strength. If you have ever felt like your past defines your future, or that you’ve made too many mistakes to turn it around, you need to read this.

The Girl Who Moved 12 Times

Jen’s story starts in Thunder Bay and stretches across Ontario, but the geography matters less than the instability. By the time she was in grade 12, Jen had attended something like 10 or 12 different schools. She was raised primarily by her mother, a white woman trying her best, while her father, an Ojibwe man, dealt with his own demons and eventual separation from the family.

Jen described herself as a chameleon. When you move that much, you learn to adapt. You learn to become whoever people need you to be just to survive the social hierarchy of a new cafeteria. "I know how to fit in when I didn't feel like I fit in," she told me. That ability to mask eventually morphed into something dangerous.

She tasted alcohol for the first time at 10 years old. By high school, she was the "fun" party girl. By her 20s, she knew she had a problem. Jen said something that hit me right in the gut: "I was always so fun until I wasn't."

For years, she masked her pain with alcohol. She was functioning—successful in a career selling seafood (yes, literal fish)—but inside, she was crumbling. The trauma of her father’s abandonment and the unhealed wounds of her ancestors were manifesting as a severe addiction. It wasn't until 2014, when her husband finally drew a hard line in the sand—threatening to leave and take their children—that Jen faced the reality of her situation.

On November 26, 2014, broken and on her knees, she surrendered. She stopped trying to control everything and asked for help from a higher power. She hasn't had a drink since. But sobriety was just the foundation. The real magic happened when she had a vivid dream of three little Indigenous girls playing in lip gloss. That dream wasn't just a random firing of neurons; it was a calling. It was the birth of Cheekbone Beauty.

Jen went from knowing nothing about the beauty industry (remember, she was in seafood!) to building a brand that not only competes with the giants but does so with sustainability and Indigenous representation at its core. She didn’t just get sober; she got purposeful.

3 Things I Learned About Turning Pain into Purpose

Talking to Jen was like a therapy session and a business seminar rolled into one. Here are the three massive takeaways that are still rattling around in my brain.

1. Forgiveness is a Superpower

We talked a lot about parents. Jen’s childhood was chaotic, and for a long time, she held a deep resentment toward her father for leaving and toward her mother for the instability. But her healing journey unlocked a powerful truth: "They were doing the best that they had with what they had."

Jen realized that her father’s absence and addiction were symptoms of the residential school system—a system designed to destroy Indigenous families. His trauma wasn't his fault, and his inability to parent wasn't a reflection of his love for her. Once she viewed her parents as flawed humans carrying their own heavy baggage, she could forgive them. And more importantly, that forgiveness freed her. It stopped the cycle of bitterness and allowed her to reconnect with her culture.

2. The "Mocktail Moment" (You Are Never Alone)

This story gave me full-body chills. Jen was six months sober, in New York City for a fancy gala. Her husband was distracted, alcohol was flowing everywhere, and the pressure was suffocating. She was lying in her hotel bed, feeling a physical weight pushing her down, telling her to drink. She decided she was going to cave. She walked up to a server, ready to throw away her sobriety and her marriage.

But before she could order a drink, the server looked at her and said, "I'd love to offer you one of our gorgeous champagne mocktails this evening."

Jen didn't ask for it. The server just knew. To Jen, that was the Creator saying, "I’ve got your back." It reminded me that when we are truly trying to heal, the universe (or God, or whatever you believe in) meets us halfway. We just have to be willing to listen.

3. Contentment and Ambition Can Co-exist

I struggle with this, and I know many of you do too. We think if we are "content," it means we’ve given up. Jen completely flipped this script. She talked about how she is incredibly happy with her life right now—her family, her sobriety, her brand. But she still wants Cheekbone Beauty to be a global legacy.

She taught me that success isn't about the next milestone; it's about being satisfied with the now while working toward the next. "If you focus on that niche... the other people will come," she said about her business. She stayed true to who she was, and the world caught up to her. You don't have to be miserable to be ambitious.

The Expert Take: Why Identity is Your Competitive Advantage

I want to take a second to connect Jen’s story to something we talk about a lot on this podcast: self-advocacy and authenticity.

For a long time, Jen tried to hide her Indigenous roots because of the shame and racism she experienced. She was called "a drunk Indian" in high school—a stereotype that terrified her because she felt she was living it. But the moment she leaned into her identity, everything changed.

Cheekbone Beauty isn't successful despite being an Indigenous brand; it is successful because it is an Indigenous brand. Jen used the values of her ancestors—specifically the idea of being stewards of the land—to create a makeup line that is sustainable and eco-friendly. She used her platform to show Indigenous youth that they belong in boardrooms and on billboards.

This is what I want you to take away: The thing you are most afraid to show the world? That "messy" part of your identity or your past? That is your superpower.

Jen didn't go to business school. She didn't know how to formulate lipstick. She didn't have funding. But she had her story, her culture, and a relentless belief that she could change the narrative for the next generation. As she told me, "Nothing is impossible. And the first step starts with believing in ourselves."

To Anyone Who Feels Like It's Too Late

Jen Harper’s journey from a jail cell (yes, she was honest about the drunk tank) to the CEO of a revolutionary beauty brand is proof that your past does not dictate your future. You can break the cycle. You can heal. And you can build something that changes the world.

Thank you for being here and holding space for these hard, beautiful conversations. If Jen’s story resonated with you, please share this post with a friend who might need a reminder that they are strong enough to start over.

You are not alone in this.

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