In an exclusive interview with Indigenous-SME Business Magazine, Moirae Choquette, author of Just Ask Your Self and founder of Tomato Wheels Lambrusco, shares a candid perspective on navigating success beyond surface-level achievements. Reflecting on moments where outward success did not match inner alignment, Moirae explores the power of self-awareness, questioning patterns, and building a life and business rooted in authenticity rather than expectation.
Interview By SK Uddin
Moirae Choquette is a Canadian Indigenous entrepreneur, author, and speaker recognized for her bold approach to business, creativity, and reinvention.
Her career has been anything but conventional, starting in geology, pivoting into marketing, and eventually leading tech and e-commerce program innovations before launching one of Canada’s fastest-growing independent Lambrusco labels.
She’s the founder of Tomato Wheels Lambrusco, a women-led sparkling red wine label crafted in partnership with a fourth-generation vineyard in Italy. The company has been featured in The Globe and Mail, The Finance Café, and Futurpreneur for shaking up traditional wine culture with authenticity and soul.
Between building a nationally distributed wine label, speaking to students across Canada and Mexico, and advocating for industry change in Ottawa, your career has taken on multiple lives. What led you to write Just Ask Your Self and what question were you beginning to ask yourself at the time?
What led me to write Just Ask Your Self wasn’t a single, intentional decision. It evolved.
This also wasn’t my first attempt at a book. I had written a manuscript prior, Control Freak, which explored the first time I recognized my own patterns—how behaviors I developed in childhood were still shaping my life and decisions 30 years later, and how my need for control was showing up, most destructively, in my romantic relationships.
That awareness opened something unexpected. It gave me a new way to observe and understand my reality. Moments would slow down, and I could see what was happening beneath the surface—both in myself and in others. It felt like seeing the same situation from multiple angles at once.
Just Ask Your Self came from that space. I began reflecting on my life, relationships, and decisions while becoming more present with my thoughts. As patterns surfaced, I started writing them down. Months into the process, I realized I had written another book—one I knew I was meant to share.
In some ways, it feels like a second life. In others, it’s just an evolution. I had to leave my corporate career and build something sustainable to create the freedom to write.
And underneath all of it was the question I had first uncovered in Control Freak: how much of my life was still being shaped by patterns I hadn’t yet learned to recognize.
In your debut book Just Ask Your Self, you challenge the idea that doing well means feeling well. Why do you think so many people stay committed to lives that look successful but don’t feel aligned?
I love this question, because it’s one so many of us can relate to.
Many of us only know what we’ve been told—what we’ve learned from our parents, teachers, peers, and the media. And for so long, it’s been the same story: the way to happiness is simple. Work harder to make more money, because when we have more money, we can spend more money. And when we have that financial freedom, we can string enough “happy experiences” together—trips, shopping, dinners, parties, vacations, renovations, that it will equate to lasting happiness.
We’ve been sold the idea that if we can just keep stacking these experiences, we’ll feel fulfilled. And because of that, we stay. We stay because it’s familiar. Because it looks right on paper. Because we don’t question it and sometimes because we don’t know what else exists beyond it.
But the truth is, while those experiences do bring moments of joy, they don’t create inner peace. And real fulfillment, real happiness—comes from a state of inner peace that can’t be built through experiences. What we often call happiness is actually distraction.
And the hardest part? We feel it but we can’t always explain it. It shows up as a quiet disconnect. A low-level dullness. A lack of motivation. But because there’s nothing concrete to point to, we override it.
We say, I just went on a trip—why don’t I feel happier?
I just did all of this—shouldn’t I feel more rested?
And instead of questioning the system, we question ourselves and keep going.
To find something deeper, it comes back to awareness. It requires taking an honest look at the life you’ve created, where you are today, and how every decision has led you here.
Look around. Your home, your relationships, your work.
And ask yourself, honestly, am I happy in this life I’ve created?
Am I content? Am I at peace?
And if the answer is no… don’t ignore it.
Start there.
Can you take us to a specific moment where you realized something in your life looked right—but didn’t feel right? What was happening, and what did you notice in yourself that you couldn’t ignore anymore?
There have been many moments like this for me, but one stands out, because on paper, everything looked great.
Tomato Wheels Lambrusco, the company I built, became a nationally distributed wine label within three years. A level of success I hadn’t imagined was possible.
And when I got there, I didn’t feel the way I thought I would. I felt like something was off and I couldn’t quite explain it.
I was watching other founders online, building personal brands, sharing their success and I told myself, this is what I have to do now. So I tried. I forced myself into it.
And nothing about it felt right. It didn’t feel authentic. I didn’t enjoy it. I didn’t like waking up knowing I had to show up that way.
And that’s when it hit me:
If this is what success requires, why doesn’t it feel good?
That question stopped me. I had to ask myself: what am I doing that I don’t actually like? And once I saw it, I couldn’t unsee it. I couldn’t keep performing a version of success that wasn’t mine.
So I stopped.
I let go of what didn’t feel right, even when it looked right and chose something quieter, more aligned, and entirely on my own terms.
In your book “Just Ask Your Self,” you invite readers into deeper self‑inquiry and unapologetic living, drawing on your own journey of reinvention and courage. What questions or practices from the book do you believe are especially powerful for small and medium‑sized business owners who feel stuck—either in their business model or in their own story as leaders ?
So often we try to separate business from our personal lives. But when you start your own business, that line disappears. And if you don’t know yourself, your business will reflect that.
Every time I speak to a group, I see the same thing. If I had built my first business from a place of ego, needing validation, acceptance, or approval, I would have failed.
Being successful is not only about having a great product, a solid business plan, or strong accounting. You can have all of that and still feel off. At some point, it takes the courage to get to know yourself. And that starts with awareness.
We hear that word all the time, awareness, but what does it actually mean and what does it look like in practice? Just Ask Your Self slows real moments down, allowing readers to see what awareness looks like in real time. Through a collection of short stories, the book reveals what lies beneath the surface of everyday life, patterns, behaviors, and quiet moments of truth we often avoid.
Because awareness is what allows you to see yourself clearly. And when you see yourself clearly, you make better decisions. Not from a need for approval, but from a grounded place of certainty. That is what makes you unstoppable as a leader.
Where can readers find Just Ask Your Self, and where can they experience Tomato Wheels Lambrusco?
I’m grateful for the national and international distribution we’ve acquired for the book. Just Ask Your Self can be found at Indigo, Barnes & Noble and Amazon as well as some of the wonderfully supportive indie book shops including Banff Trading Post, Pages of Kensington, Kinder Books, Strong Nations, Mosaic Books.
Our Lambrusco is available in liquor stores and restaurants across Canada. If anyone needs help locating a bottle in their city, they can shoot us a message on Instagram at @tomatowheels and we will point them in the right direction.
You can find out where I will be speaking next via moiraechoquette.com.
Disclaimer:
Indigenous-SME Business Magazine is committed to providing insightful interviews that highlight the successes and challenges faced by small and medium-sized businesses. The views expressed in this interview are those of the guest and may not reflect the opinions of the magazine or its affiliates.
