EP 285 – Kendra MacDonald: Building a Career That Grows With You
Release Date: 08/21/2025
EP 294 - Rest. In. Peace.
Paper Napkin Wisdom
Some episodes of Paper Napkin Wisdom are easy to listen to, packed with energizing insights and clear strategies for growth. Others are heavier — not because they lack value, but because the wisdom forces us to pause, reflect, and wrestle with the uncomfortable. Episode 294 is one of those conversations. This week, Govindh sits down with three little letters we all know: RIP. We’ve all said them. We’ve read them on tombstones, typed them in comments, whispered them at funerals. But how often do we really consider what they mean? And what happens when they appear in the midst of...
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EP 293 – Steven Rothberg: If a Customer Wants to Pay More, Let Them
Paper Napkin Wisdom
When you sit down with someone like Steven Rothberg, Founder and Chief Visionary Officer of , you expect to hear insights about hiring, technology, and the future of work. What you might not expect is a napkin that sums up decades of wisdom in a sentence so straightforward it almost sounds too simple: “If a customer wants to give you more money, find a way of making that happen. $$$” At first glance, it feels like sales advice. But during our conversation, it became clear that Steven’s napkin is less about sales tactics and more about mindset. It’s about curiosity,...
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EP 292 - Edge of the Napkin #3: “Who’s the best partner you ever had? (Secret) … It’s you.”
Paper Napkin Wisdom
Partnership is one of the most powerful words in leadership and in life. We spend years searching for the right business partner, co-founder, or even life partner. But here’s the twist on this week’s Paper Napkin Wisdom: the greatest, most important partnership you’ll ever have is not with someone else—it’s with yourself. The napkin for Episode 292 asks the provocative question: “Who’s the best partner you ever had?” And then delivers the unexpected truth: (Secret)… it’s you. In this episode, Govindh dives deep into the nature of the...
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EP 291 – Jennifer McKenna - The Prosperity Formula: Familiar → Faith → Fulfillment
Paper Napkin Wisdom
Jennifer McKenna, founder of JMac Consulting, is an accomplished business strategist, executive coach, and creator of The JMac Method. With decades of experience guiding leaders and organizations through transformation, Jennifer has built her reputation on blending practical business strategy with a deep commitment to values, authenticity, and growth. She has coached Fortune 500 executives, entrepreneurs, and visionaries to align who they are with what they do. On Paper Napkin Wisdom, Jennifer shares her Prosperity Formula — a deceptively simple but powerful framework to help...
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EP 290 – Andrew Safnauer: Find Your Way Over the Wall
Paper Napkin Wisdom
In Episode 290 of Paper Napkin Wisdom, I had the pleasure of sitting down with Andrew Safnauer, a seasoned leader and executive with a wealth of experience in management, strategy, and innovation. Andrew has held leadership roles across diverse industries and today brings his insights into resilience, adaptability, and persistence. His wisdom is captured on a single napkin: “Find your way over the wall.” At first glance, it’s a simple metaphor. But as Andrew shares, this idea has been a recurring theme throughout his life and career, one that continues to guide him...
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EP 289 - The Edge of the Napkin: Friction vs. Flow
Paper Napkin Wisdom
In Episode 289 of Paper Napkin Wisdom, host Govindh Jayaraman takes us deeper into the next evolution of his work: The Edge of the Napkin. This isn’t just about wisdom captured in simple strokes anymore — it’s about stepping into the tension between friction and flow, and understanding the rhythms of creativity and growth. The napkin for this episode sets the stage: a stick figure caught between jagged lines of friction and the upward curve of flow, alongside two key modes — Seminal (Spark) and Gestational (Build). At its heart, the question posed is simple but powerful: Are...
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EP 288 – Katy Spada: Build the World You Wish Existed
Paper Napkin Wisdom
When Katy Spada sat down with me on Paper Napkin Wisdom, she brought a napkin that was more than just words — it was a challenge: “Build the world you wish existed for your younger self, and for those who come next.” Katy isn’t just an entrepreneur. She’s a mother of two (ages 7 and 4), a storyteller, and the founder of , a lifestyle and apparel company that’s grounded in values of creativity, heritage, and intentional living. What makes her story remarkable is how deeply personal it is. As she says, she never set out to be an entrepreneur — she calls...
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EP 287 – Permission, Structure, and Social Media Success with Sam Toles
Paper Napkin Wisdom
In this episode of Paper Napkin Wisdom, Govindh Jayaraman welcomes Sam Toles, a digital media pioneer and storyteller with decades of experience building audiences, brands, and communities. Sam is the CEO and co-founder of , a platform designed to transform civic engagement by helping communities and governments create stronger, more transparent conversations online. Sam’s career has spanned leadership roles at MGM, Vimeo, Bleacher Report, and Warner Bros., and throughout it all he has stayed focused on how creativity, structure, and permission come together to unlock growth. His...
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EP 286 - Introducing the Edge of the Napkin
Paper Napkin Wisdom
In this special episode of Paper Napkin Wisdom, I (Govindh Jayaraman) take a step back to reflect on the journey we’ve been on together — over 280 episodes filled with wisdom, stories, and lessons from incredible leaders, entrepreneurs, and difference makers. The napkin for this episode reads: “Introducing the Edge of the Napkin.” It’s a phrase that captures both a transition and an expansion. The napkin has always been a place for distilled wisdom — one sentence, one thought, one principle that could change everything if applied. But now, we’re venturing into...
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EP 285 – Kendra MacDonald: Building a Career That Grows With You
Paper Napkin Wisdom
Careers 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...
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.