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EP 302 – The Choice of Leadership with Chris Thomson (Part 2 of 2)

Paper Napkin Wisdom

Release Date: 10/02/2025

EP 314 - Believing Is Seeing (Edge of the Napkin Series #12) show art EP 314 - Believing Is Seeing (Edge of the Napkin Series #12)

Paper Napkin Wisdom

There’s a phrase we’ve all inherited without ever asking whether it serves us: “I’ll believe it when I see it.”  It sounds reasonable. It sounds mature. It sounds like the responsible stance of someone who has been around long enough to be cautious.  But anyone who has ever built something meaningful — a business, a team, a movement, or even a new version of themselves — knows the truth beneath that old saying:  “Seeing” has never created belief. Belief is what creates the ability to see.  That’s the heart of today’s napkin thought:...

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EP 313 - Listening & Learning with Shivani Dhamija show art EP 313 - Listening & Learning with Shivani Dhamija

Paper Napkin Wisdom

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EP 312 - Build for Value — Not for the Hype: How some AI Companies are Winning, and others aren't (Edge of the Napkin #11) show art EP 312 - Build for Value — Not for the Hype: How some AI Companies are Winning, and others aren't (Edge of the Napkin #11)

Paper Napkin Wisdom

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EP 311 - Dr. Jenny Hoffmann: Open Up! Lead with Curiosity, Empathy, and Connection show art EP 311 - Dr. Jenny Hoffmann: Open Up! Lead with Curiosity, Empathy, and Connection

Paper Napkin Wisdom

    Today on Paper Napkin Wisdom, we welcome Dr. Jenny Hoffmann, a leader in health-tech innovation who currently serves as Executive Director at the New England Medical Innovation Center (NEMIC). With a rich background in healthcare strategy and technology deployment, Jenny has spent her career bridging clinical insight with entrepreneurial energy, helping organizations turn innovative ideas into meaningful patient-outcomes. In this episode, we dive deep into how leaders can lean into vulnerability, curiosity, empathy and connection — the key themes captured on her paper...

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EP 310 - Make Believe: The Stories Entrepreneurs Tell Themselves (Edge of the Napkin #10) show art EP 310 - Make Believe: The Stories Entrepreneurs Tell Themselves (Edge of the Napkin #10)

Paper Napkin Wisdom

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EP 309 - Jon Rosemberg — Survival Is Instinct, Thriving Is a Choice show art EP 309 - Jon Rosemberg — Survival Is Instinct, Thriving Is a Choice

Paper Napkin Wisdom

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EP 308 - Flexibility Is the Only True Hedge – Edge of the Napkin #9 show art EP 308 - Flexibility Is the Only True Hedge – Edge of the Napkin #9

Paper Napkin Wisdom

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Paper Napkin Wisdom

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EP 306 - HOW? The Freedom to Create the Future - Edge of the Napkin #8 show art EP 306 - HOW? The Freedom to Create the Future - Edge of the Napkin #8

Paper Napkin Wisdom

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EP 305 - Solve a Real Problem. Make It Beautiful. Care Like Hell. - With Nancy Johnston show art EP 305 - Solve a Real Problem. Make It Beautiful. Care Like Hell. - With Nancy Johnston

Paper Napkin Wisdom

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In this second half of our powerful conversation with Chris Thomson, we dive deeper into the mindset, discipline, and leadership lessons that have guided him through decades of transforming students into high-performing entrepreneurs. Chris is the Head Coach of the Student Works Management Program, a business that has trained thousands of young leaders across Canada. His story is one of building people, systems, and a culture that thrives on ownership and accountability. 

His wife, Helen Thomson, is his business partner and CEO of the Student Works Management Program and together they are among the most dynamic pairs of entrepreneurs in the country. Their program has likely help forge more Canadian entrepreneurs than any other program.  

He is also the host of the very popular Leaders of Tomorrow podcast where he features young and dedicated entrepreneurs on their journey to forge their own path in the world. 

Chris’ napkin for this episode reminds us that leadership is not about the title or the authority someone gives you—it’s about the intentional choice you make every day. This distinction is simple yet transformative. It forces us to confront whether we are showing up with the courage, responsibility, and consistency that leadership truly demands. 

Choosing Growth Over Comfort 

Chris points out that most people are wired to choose comfort—it’s the path of least resistance. But leadership requires choosing growth, even when it feels uncomfortable. Growth demands risk, vulnerability, and a willingness to fail forward. His message is clear: every great leader has to wrestle with the temptation of comfort, and the best ones consistently choose growth. 

Take Action: Next time you’re faced with a difficult decision, pause and ask yourself: Am I choosing growth, or am I defaulting to comfort? Write it down and commit to the growth path. 

Building a Culture of Accountability 

One of the strongest threads in Chris’ work is accountability. At Student Works, young leaders are taught not just to deliver results but to own their commitments fully. Chris emphasizes that accountability is the backbone of trust and performance. Without it, teams drift. With it, they thrive. 

Take Action: Introduce a simple accountability rhythm in your team this week. It could be a weekly check-in where everyone reports on one promise made and one promise kept. 

The Discipline of Consistency 

Chris makes it clear that success isn’t built on flashes of brilliance but on disciplined, consistent effort. Leaders set the tone by showing up every day, prepared, focused, and ready to do the hard things. That consistency compounds over time and creates the culture others can rely on. 

Take Action: Identify one leadership behavior you want to model consistently for your team (e.g., starting meetings on time, always closing the loop on commitments). Practice it relentlessly for the next 30 days. 

Mentorship as Multiplication 

A powerful insight Chris shares is the multiplier effect of mentorship. When a leader invests deeply in someone else’s growth, that impact ripples outward exponentially. The students Chris has mentored are now leaders who are mentoring others—creating a legacy of growth and excellence. 

Take Action: Identify one person in your world who has potential but needs encouragement. Reach out, invest time, and open a door for them. 

Owning Your Leadership Journey 

At the core of Chris’ message is ownership. Leaders don’t wait for permission to step up—they own their journey, their choices, and their impact. Leadership is not a someday aspiration. It’s a today decision. 

Take Action: Write down your personal leadership commitment on a napkin. What is the one sentence that captures the leader you want to be? Post it where you’ll see it daily. 

About Chris Thomson 

Chris Thomson is the Head Coach and Leader of the Student Works Management Program, an organization dedicated to building the next generation of entrepreneurs through hands-on business experience. Over decades, Chris has coached thousands of university students to run their own businesses, building a legacy of leaders across Canada. Connect with Chris on LinkedIn and follow the Student Works Management Program for more insights. Follow the Leaders of Tomorrow Podcast as well.

At Paper Napkin Wisdom, we believe small ideas can spark big change. What’s your biggest takeaway from Chris’ wisdom? Grab a napkin, write it down, and share it with the hashtag #PaperNapkinWisdom. Your next big shift might just start with one small choice.