The Calgary Sessions

Some businesses grow fast and disappear. Others last through exits, downturns, and restarts.

In this episode, Shawn Freeman talks about why relationships are the real structure holding a business together. Not as a value statement, but as something tested through building companies, selling one, stepping away, and starting again.

The conversation moves through how trust compounds quietly over time, why repeated friction is often a warning rather than a challenge, and how founders learn to make decisions without forcing outcomes. Shawn shares how confidence, energy, and alignment show up in very practical ways, even for leaders who think analytically.

Rather than focusing on tactics or growth strategies, this episode sits with how people think once they’ve seen businesses succeed and fail up close. It’s a reflection on why people follow people, why impact outlasts metrics, and why the businesses that endure are usually built on relationships long before they are built on plans.

Connect with our guest, Shawn Freeman:

• ⁠⁠⁠⁠⁠⁠⁠Website⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠

Connect with Jeff Humphreys

• ⁠⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠

Podcast Location & Production:

• ⁠⁠⁠⁠⁠⁠⁠Off Set Studios

Fear shows up quietly. It shapes how we make decisions, how we measure progress, and how long we stay in situations that no longer feel right.

In this episode, I sit down with Dr. Laura Hambley Lovett, an organizational psychologist, researcher, and author, to talk about what happens when logic, effort, and planning stop being enough on their own.

We explore why life can start to feel like a constant gap, where the horizon keeps moving and progress never quite feels satisfying. Why comparison, noise, and fear distort how we see ourselves and our work. And why intentionally looking back at what you’ve already built is often the missing piece for clarity and fulfillment.

Dr. Laura also shares how trust, intention, and timing play a role in moving forward when certainty isn’t available. Not as blind optimism, but as a grounded way of taking the next step with purpose, support, and self-awareness. We talk about fear and risk, entrepreneurship and mindset, and the difference between pushing harder and aligning your energy with work that actually adds value.

The conversation also moves into leadership and systems. Why toxic workplaces often persist through avoidance and silence. What compassionate leadership actually looks like in practice. And why honest, difficult conversations are essential for healthy teams and long-term trust.

This is a thoughtful, practical conversation about navigating uncertainty, making grounded decisions without guarantees, and learning how to move forward when fear tries to keep you still.

Connect with our guest, Dr. Laura:

• ⁠⁠⁠⁠⁠⁠Website⁠

• ⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠LinkedIn⁠

Connect with Jeff Humphreys

• ⁠⁠⁠⁠⁠⁠Website⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠

Podcast Location & Production:

• ⁠⁠⁠⁠⁠⁠Off Set Studios

Life doesn’t usually offer clarity when you need it.

In this episode, reflects on what it means to keep moving forward through uncertainty. From early responsibility and family instability to becoming a husband, father, and leader while still figuring things out, his story unfolds without clean timelines or clear answers.

Michael is a Canadian speaker, author, and founder whose work has grown out of lived experience rather than strategy. This conversation explores presence without control, responsibility before readiness, and how meaning often shows up later than the moments that shape us. It’s a grounded look at continuing on, not because you’re certain, but because life keeps going.

Connect with our guest, Michael Chiasson:

• ⁠⁠⁠⁠⁠Website

• ⁠⁠⁠⁠⁠Instagram⁠⁠

• ⁠⁠⁠⁠⁠LinkedIn

Follow Jeff Humphreys

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• ⁠⁠⁠⁠⁠TikTok⁠⁠⁠⁠⁠

• ⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠

Podcast Location & Production:

• ⁠⁠⁠⁠⁠Off Set Studios

Cassie Hawrysh has lived most of her life in high pressure environments. She grew up around adults, learned responsibility early, and carried that into sport where effort and expectations shaped almost everything she did. When she became one of the top skeleton athletes in the world, the drive that pushed her forwardalso became the thing she had to untangle.

This episode looks at what happens when hard work does not lead to the outcome you imagined, and how a person rebuilds when they have to let go of the identity they carried for years. Cassie talks about the pull of ambition, the weight of almost moments, and the slow process of figuring out who she was outside of performance.

It is a grounded conversation about pressure, transition, and the reality of starting again in your thirties.Cassie’s story is shaped by effort, honesty, and the long path toward a lifethat finally feels like her own.

Connect with our guest, Cassie Hawrysh:

• ⁠⁠⁠⁠Instagram⁠

• ⁠⁠⁠⁠Website⁠

• ⁠⁠⁠⁠LinkedIn

Follow Jeff Humphreys

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• ⁠⁠⁠⁠TikTok⁠⁠⁠⁠

• ⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠

Podcast Location & Production:

• ⁠⁠⁠⁠Off Set Studios

Some people grow up fast because life demands it. Teika did. She carried responsibility early and learned to pay attention young. That awareness shaped how she understood people, how she stayed steady in difficult moments, and howshe found confidence in structure and discipline long before tattooing entered her life.

This episode gets into the experiences that shaped her thinking. The pressure of growing up early. The instinct to read a room because you have to. The discipline built through martial arts. The years spent apprenticing while raising a kid. And how tattooing eventually became the place where all of those traits made sense together.

Tattooing is her craft, but the story runs wider. It connects with anyone who has had to grow up early, carry more than people realized, or build their identity through steady work and honest self-understanding.

Connect with our guest, Teika Hudson:

• ⁠⁠⁠Instagram

• ⁠⁠⁠Website

Follow Jeff Humphreys

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• ⁠⁠⁠TikTok⁠⁠⁠

• ⁠⁠⁠LinkedIn⁠⁠⁠

Podcast Location & Production:

• ⁠⁠⁠Off Set Studios

Success rarely comes from a straight line. Nic Beique built Helcim into one of Canada’s most respected fintech companies, but the road that shaped him was full oftiming, luck, perseverance, and the kind of complicated lessons that make you who you are.

In this episode, Nic talks openly about the parts of growth people don’t see. The doubt that shows up at every level. The moments where confidence fades. The long stretches where you question your path. And the unexpected breaks that only appear after you keep going longer than you thought you could.

This conversation is for anyone trying to build something real.Founders, creators, young professionals, and people figuring out the next step in their careers. If you’re navigating uncertainty, wrestling with imposter thoughts, or trying to trust your path, Nic’s story gives you something to hold on to.

Simple, honest insight from someone who has lived every turn of the journey.

Connect with our guest, Nic Beique:

• ⁠⁠Website⁠⁠

• ⁠⁠Linkedin⁠

Follow Jeff Humphreys

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• ⁠⁠TikTok⁠⁠

• ⁠⁠LinkedIn⁠⁠

Podcast Location & Production:

• ⁠⁠Off Set Studios

What if you don't need a "5-year plan" to be successful?

We're all pressured to find our one "passion" and follow a perfect, linear path. But what if that's not how the most interesting careers are built?

Laura Naaykens is a former NCAA athlete who, after an injury, found herself in a complete identity crisis. She didn't have a grand plan; she just started... figuring it out. Her journey is a playbook for "accidental" success, showing how she pivoted from sports to "accidentally" founding a data science firm, not by following a passion, but by saying "yes" to problems she didn't know how to solve and then getting good at them.

It’s a conversation about the power of self-awareness, why competence is more valuable than passion, and how to build a life on your own terms.

Connect with our guest,Laura Naaykens:

• ⁠Website⁠

• ⁠Linkedin

• ⁠Instagram

Follow Jeff Humphreys

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Podcast Location & Production:

• ⁠Off Set Studios

Manifestation isn't just "thinking positive." It can be a practical, daily tool, as simple as a specific morning routine—from a cold plunge to how you write in a journal—that you use to run your life and business.

These insights come from Brent Boucher, a Calgary entrepreneur whose story is a perfect example of what I call "grey thinking". He built his business from a place of deep personal struggle and uses these tools to navigate the real-world emotional "peaks and valleys" of running a company.

This is just one part of a much larger conversation. Hear Brent Boucher's full story on The Calgary Sessions podcast (Episode 178).

Listen to the full episode

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• ⁠⁠⁠⁠Spotify

Connect with our guest, Brent Boucher:

• ⁠Website⁠

Follow Jeff Humphreys

• ⁠Website⁠

• ⁠Instagram⁠

• ⁠TikTok⁠

• ⁠LinkedIn⁠

Podcast Location & Production:

• ⁠Off Set Studios

How do you build a life when your childhood is defined by instability?

Brent Boucher is a Calgary entrepreneur who built a successful motorcycle shop and finance company from scratch. But his journey started in a place of deep trauma, navigating family mental health crises and leaving school in Grade 11 just to pay the bills.

In this conversation, Brent shares the unconventional origin story of his career (which involves a stolen dirt bike) and his core philosophy: you have to seek discomfort to perform at your best. This is a raw conversation about prioritizing grit over talent and building a life by "feeling the end picture" rather than following a rigid plan.

Follow The Calgary Sessions podcast for more stories like this.

Connect with our guest, Brent Boucher:

• Website

Follow Jeff Humphreys

• Website

• Instagram

• TikTok

• LinkedIn

Podcast Location & Production:

• Off Set Studios

Dr. Matt Brown had his entire life planned: pro football, then medical school. He details the "helmet to helmet" hit that ended his career and the "messy" mental health transition that followed.

He discusses the stigma that kept him from seeking help and the pivotal moment he sat on the field and asked, "Who am I without football?"—and heard "deafening... silence."

Ep177 Guest: Dr. Matt Brown, Mental Performance Coach

Host: Jeff Humphreys

Where to Connect:

• YouTube: https://www.youtube.com/@jeffhumphreys

• Instagram: https://www.instagram.com/jeffhumphreys

• Website: https://www.jeffhumphreys.ca