The Choice of Leadership with Chris Thomson (Part 2 of 2)
Release Date: 10/02/2025
Cut the Anchor: Why Your Most Powerful Resolution for 2026 Might Be a STOP List - Edge of the Napkin Series #18
Paper Napkin Wisdom
This time of year, something familiar happens. We turn the page on the calendar and feel the pull to do something different. We reach for a word like resolution and instinctively pair it with action. More discipline. More consistency. More output. More effort. Most resolutions are framed as additions — new habits, new systems, new rules we promise ourselves we’ll finally follow. But what if the most powerful move forward isn’t about what you start doing? What if real...
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People Come for the Work. They Stay for the Team. – Wintress Odom, CEO The Writers for Hire
Paper Napkin Wisdom
Wintress Odom is the Founder and CEO of The Writers For Hire, a company built on clarity, discipline, and consistently high-quality work. From the outside, it’s easy to assume the success came from systems, execution, and technical excellence alone. But on her paper napkin, Wintress wrote something deceptively simple: “People come for the work. They stay for the team.” That sentence didn’t come from a leadership book. It came from lived experience — from building a business, leading...
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Presence Over Presents: The Ultimate Gift You Can Give Yourself This Holiday
Paper Napkin Wisdom
The holidays come wrapped in familiar language. Slow down. Rest. Be present. Unplug. It sounds right. It even sounds desirable. And yet, for many leaders and entrepreneurs, it doesn’t always land. If anything, the holidays can quietly amplify a tension that’s been humming all year. Because while the world appears to be pausing, something inside you may still be moving. Measuring. Reviewing. Assessing. For years, that’s where I lived. When the...
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Turn the Other Cheek, Smile — and Mean It – David Miller
Paper Napkin Wisdom
There’s a particular kind of wisdom that doesn’t shout. It doesn’t posture. It doesn’t try to win the room. It shows up quietly, often after experience has taken its toll, and says: this way works better. That’s the kind of wisdom David Miller brought to this conversation. On his paper napkin, David wrote a deceptively simple line: “Turn the other cheek, smile :) and mean it!” At first glance, it sounds like something we’ve all heard before — maybe even dismissed. Too soft....
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Seeds Grow in the Soil: Why the Most Important Progress Is Invisible (Yet)
Paper Napkin Wisdom
There are seasons where doing the work feels strangely unrewarding. You’re showing up. You’re staying consistent. You’re doing what you said you would do. And yet — nothing obvious is happening. No external validation. No visible breakthrough. No clear sign that you’re “on track.” That’s usually when doubt starts whispering questions we don’t want to answer: Is this actually working? Am I wasting time? Shouldn’t I be further along by now? This Edge of the Napkin episode is about that exact season — the one...
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“Your Revenue Is Hiding in Plain Sight” — Sailynn Doyle on the 80/20 Shift That Changed Everything
Paper Napkin Wisdom
There’s a moment in every entrepreneur’s journey when the hustle stops feeling heroic and starts feeling heavy. For Sailynn Doyle — business systems strategist, former home-care franchise owner, and founder of Passion • Purpose • Posture — that moment came sitting alone in her car at 9 AM on a Tuesday, exhausted and crying before another 12-hour day. From the outside, she was a success story: a million-dollar business by year three. On the inside, she was drowning in the weight of the work. Endless demands. Constant interruptions. Team members who depended on her for every...
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Nothing to Prove. Everything to Be.
Paper Napkin Wisdom
There’s a moment in every leader’s life when they look around the “room” they’re in — not the physical room, but the emotional one, the psychological one, the internal one — and ask: “How much of who I am today was shaped by the right voices… and how much by the wrong ones?” For years, Govindh Jayaraman — founder of Paper Napkin Wisdom — sat in rooms filled with people who called themselves friends, collaborators, supporters. And many of them were exactly that. They challenged ideas. They sharpened thinking. They asked questions that helped build the...
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Dan Perry & Michael Serapiglia – “If You Get Lost, Enjoy the View Around You”
Paper Napkin Wisdom
Some stories begin with a business plan. Others begin with a feeling — a deep, lived truth that travel isn’t just about going somewhere, but about finally being somewhere without fear. That’s the story behind Toto Tours. When founder Dan Ware launched the company in 1990, LGBTQ+ travelers faced a world far less welcoming than it is today. Travel was often an act of courage. Safety wasn’t guaranteed. Connection wasn’t a given. And yet Dan believed something radical: that the world belonged to everyone, and that queer people deserved to explore it without shrinking,...
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Be the Man in Someone’s Corner
Paper Napkin Wisdom
There are times in life when wisdom doesn’t show up quietly. It doesn’t whisper. It doesn’t tap you gently on the shoulder. Sometimes it arrives like a jolt — like your heart recognizing something before your brain can process it. That’s how this episode began. If you’ve been following along, you know it’s been a hard season in our home. Stacey’s father — my father-in-law — has been moving through the final stages of his cancer journey. And while there is an entire conversation to be had about the health, the living, and the complexity of that experience… this...
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Noah Ellis — Do The Thing
Paper Napkin Wisdom
There’s a moment in every entrepreneur’s life when the universe stops whispering and starts shouting. A moment where the next level isn’t waiting behind brilliance or luck or timing — it’s sitting directly behind the one thing we don’t want to do. For Noah Ellis, founder of Ofland and a hospitality leader who’s spent his life building concepts, teams, and experiences, that moment became a clarity-inducing mantra so important that he didn’t just write it down… he tattooed on his body: Do the thing. Noah’s wisdom is the kind that doesn’t land with...
info_outlineIn 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.