EP 285 – Kendra MacDonald: Building a Career That Grows With You
Release Date: 08/21/2025
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
Paper Napkin Wisdom
In this episode of Paper Napkin Wisdom, Govindh Jayaraman sits down with Shivani Dhamija, founder of Shivani’s Kitchen — a culinary brand rooted in authentic Indian flavors and fueled by a passion for empowering others through food. From her humble beginnings selling spice blends and sauces at local markets in Nova Scotia to building a thriving food-manufacturing business, Shivani’s journey is as flavorful as her recipes. At the heart of her success lies a simple napkin message: “Listening & learning.” Two small words that capture a massive truth about...
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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)
Paper Napkin Wisdom
Edge of the Napkin #11 There’s a feeling that sweeps through every era of innovation — that electrifying sense of this is it. The next big wave. The one that’s going to change everything. In this episode of Edge of the Napkin, Govindh Jayaraman dives into what happens when high-expectation innovation collides with reality — when the future we bet on becomes today’s proving ground. The AI boom, once the unstoppable tide lifting every boat in sight, is now pulling back. Markets are correcting. The water is getting choppy. And what’s being revealed isn’t failure — it’s truth....
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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)
Paper Napkin Wisdom
Make Believe: The Stories Entrepreneurs Tell Themselves (Edge of the Napkin #10) Every entrepreneur lives inside a story — the question is, who’s writing yours? If you’ve ever had a morning where nothing goes right — you stub your toe, drop your keys, spill coffee on your white shirt before 8 a.m. — you know the script that starts to play in your mind: “It’s gonna be one of those days.” And somehow, it is. Everything that follows seems to prove the story true. But the opposite happens too. You walk out the door feeling light, ...
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EP 309 - Jon Rosemberg — Survival Is Instinct, Thriving Is a Choice
Paper Napkin Wisdom
When you meet Jon Rosemberg, you immediately sense two things — depth and discipline. He’s a behavioral scientist, author, and executive coach who has spent years exploring how we, as humans, can move beyond mere survival into a state of thriving. His work combines neuroscience, psychology, and lived experience, and it’s reflected powerfully in his new book, A Guide to Thriving: The Science Behind Breaking Old Patterns, Reclaiming Your Agency, and Finding Meaning. On his paper napkin, Jon wrote just seven words: “Survival is instinct, thriving is a choice.” At...
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EP 308 - Flexibility Is the Only True Hedge – Edge of the Napkin #9
Paper Napkin Wisdom
In a world where volatility has become the norm — prices swing, markets shake, politics polarize, and technology rewrites the rules daily — one question stands out for leaders, entrepreneurs, and anyone simply trying to navigate life: How do we hedge against uncertainty? Not with gold. Not with cash. Not with control. But with flexibility. That’s the essence of this week’s Edge of the Napkin. On my napkin, a single word runs across the center: RISK. Below it — Rigidity → Fragility. Above it — Flexibility →...
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EP 307 - Simone Kelly - Build a Business You Love (But Not Your Hobby)
Paper Napkin Wisdom
When Simone Kelly first began helping families navigate the complexities of senior care, she didn’t just build a company—she built a movement. As the founder and CEO of Seniornicity, Simone’s mission is rooted in empathy, connection, and empowerment. Her company bridges the gap between older adults, families, and trusted care providers, making it easier for people to age well, together. But the napkin she brought to Paper Napkin Wisdom goes deeper than business strategy—it’s about protecting your passion and preserving your peace. “Build a business that you love,...
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EP 306 - HOW? The Freedom to Create the Future - Edge of the Napkin #8
Paper Napkin Wisdom
Sometimes, the smallest words hold the biggest weight. In this episode of Edge of the Napkin, Govindh Jayaraman dives deep into one of the most overused — and misunderstood — words in leadership: “How.” We use it constantly. We think it’s helpful. But as Govindh reveals, how can be both the key to progress — and the invisible wall that keeps us from growing. We say things like: “That’s not how it’s done.” “That’s not how we do things here.” “Let me show you how I want that done.” “We tried that how before...
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EP 305 - Solve a Real Problem. Make It Beautiful. Care Like Hell. - With Nancy Johnston
Paper Napkin Wisdom
When you meet Nancy Johnston, you can immediately sense the combination of depth and purpose behind everything she touches. She’s the founder and CEO of Truuce, a company built around reimagining human connection, well-being, and design in the modern world. Her leadership bridges the emotional and the practical — weaving care, creativity, and clarity into every solution she creates. In this episode of Paper Napkin Wisdom, Nancy shares a simple but transformative philosophy written on her napkin: “Solve a real problem. Make it beautiful. Care like...
info_outlineCareers aren’t meant to be lived on repeat. In this episode of Paper Napkin Wisdom, we sit down with Kendra MacDonald, CEO of Canada’s Ocean Supercluster, a leader who has spent her career helping organizations innovate, adapt, and push boundaries. Kendra has been recognized for her work in transformation and leadership across industries, and she brings her wisdom to the napkin with a deceptively simple but powerful message.
On her napkin, Kendra wrote:
“Make sure your career is 25 years, not 1 year 25 times. What will you learn this year?”
This phrase, first heard from one of her professors in university, has echoed through her journey and shaped how she approaches growth.
The Wisdom of 25 Years
When Kendra first heard this idea as a 22-year-old student, she didn’t grasp its depth. At the time, her vision of a career was linear: find a job, build a life, move forward. But as the years unfolded, she realized the trap many fall into—repeating the same year of work experience over and over again.
In her words, the difference between “25 years of experience” and “one year repeated 25 times” is profound. The former means growth, change, and learning. The latter is stagnation.
Kendra emphasized that growth in a career isn’t about time served, but about intentional learning. Each year should bring a new challenge, a new perspective, or a new skill. Without that, time passes but wisdom doesn’t accumulate.
5 Key Takeaways from Kendra MacDonald
1. Don’t Repeat Years—Grow Them
Many professionals fall into the trap of doing the same work, the same way, year after year. Kendra’s reminder is that repeating one year 25 times is not growth.
Take Action: Audit your last 12 months. Identify one thing you learned or improved. If you can’t name it, commit to changing that this year.
2. Anchor Each Year in a Learning Goal
Kendra reframes career development with a simple, forward-looking question: “What will you learn this year?” This shifts the focus from passive time spent to active growth pursued.
Take Action: Write down one specific learning objective for this year—whether it’s a skill, a mindset, or an experience—and track progress monthly.
3. Embrace Discomfort as a Growth Engine
Kendra shared that her own leaps forward came when she stepped into new industries or roles that stretched her beyond her comfort zone. Stagnation is safe but it doesn’t lead to growth.
Take Action: Choose one area where you’ve become too comfortable. Seek a project, collaboration, or responsibility that forces you to learn something new.
4. Redefine Career Success Beyond Longevity
A long career without growth isn’t success—it’s inertia. Success is measured by the depth of learning, adaptability, and impact created along the way.
Take Action: Redefine your career scorecard. Instead of only measuring years served, track skills gained, leadership challenges tackled, and innovations you contributed to.
5. Lead With a Culture of Learning
For leaders, this napkin wisdom applies not just personally but organizationally. Teams grow stale when they repeat the same patterns year after year. Growth happens when learning is embedded into the culture.
Take Action: At your next team meeting, ask Kendra’s question: “What will we learn this year?” Make it a collective challenge and revisit it quarterly.
About Kendra MacDonald
Kendra MacDonald is the CEO of Canada’s Ocean Supercluster, a national initiative focused on transforming Canada’s ocean economy through collaboration, innovation, and technology. She has extensive leadership experience across sectors, with a background that includes senior roles in Deloitte Canada and a career dedicated to driving transformation and growth.
Connect with Kendra on LinkedIn.
Call to Action
What about you? Don’t let this year be a copy of the last. Ask yourself:
📝 “What will I learn this year?”
Write it down on a napkin, take a picture, and share it with the world using #PaperNapkinWisdom.
Because your career isn’t about years served—it’s about years lived and learned.