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 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.