The New Standard for Ambition
How unshakeable character gives us permission to build for the world stage.
Our definition of ambition is not ambitious enough.
Ambition (noun) — An ardent desire for rank, fame, or power.
— Merriam-Webster
This definition, and others like it, is accurate only for ambition without principles. It describes a raw desire for status, a pursuit of power for its own sake, devoid of constraints and driven by pure want.
When ambition is defined solely by what we take from the world, stating a massive goal out loud—“I want to build a billion-dollar company” or “I want to transform this industry”—gets heard as selfish, arrogant, or power-hungry.
To avoid that judgment, we often keep our heads down, stay out of the noise, and work in silence.
But working in silence carries a penalty: if we don’t say the goal out loud, people can’t help us. The right partners, capital, and teammates can’t find us. When talented people working on critical problems—in housing, healthcare, or climate—stay hidden, progress in those areas slows.
We need a standard that allows us to state big goals without being dismissed as self-serving.
Fortunately, I’ve observed a different framework in action: a standard that is deeply principled, built for the long run, and massive in scope. It quietly drives some of the world’s most enduring success stories.
If you’ve ever felt like your ambition needed permission, here’s the standard that gives it to you:
Unapologetic Ambition (noun) — The pursuit of meaningful goals guided by uncompromising principles.
— Not Sorry
When we know what we won’t compromise, we can pursue everything else without apology. Principles create permission.
Engineers ask for the promotions and salaries they’re worth. Founders say “billion-dollar company” in the first meeting. Athletes state their drive to make the top roster without burying it under false modesty.
We stop shrinking. We ask for what we’ve earned, state our grandest visions, and step forward to lead.
To see what this looks like in practice, I asked dozens of leaders to define their own “not sorry” statements by answering two questions:
What goal(s) are you not sorry for pursuing? (This names your ambition.)
What principle(s) guide how you pursue it/them? (This names your character.)
Neil Cawse • Geotab
Building a global telematics giant from outside the venture ecosystem
Operating out of Oakville, Ontario, Neil transformed an entire industry by turning proprietary black boxes into open, transparent data systems. He built Geotab into a $1 billion ARR company processing 100 billion daily data points from millions of vehicles—without a cent of venture capital—ultimately beating Silicon Valley’s hyper-funded giants for a $314 million government contract.
“I’m not sorry for bringing ruthless transparency to an industry built on black boxes.”
The Principles: Do the right thing for the long run. Check your ego at the door. Measure, reflect, and improve.
By discarding VC money, Neil protected his long-term values from short-term growth pressures. He built an empire on transparency, refusing shortcuts that compromise long-term trust. He is proof that checking your ego isn’t a soft skill, but a defensive moat.
Mike Wessinger • PointClickCare
Scaling a $1B software powerhouse on pure customer trust
Based in Mississauga, Ontario, Mike transformed healthcare records when the industry still relied on paper and fax machines. He scaled PointClickCare to $1 billion in ARR entirely on month-to-month contracts, choosing to earn his customers’ trust every single day instead of locking them into annual deals like everyone else.
The Principles: Over-index on customer delight, not fundraising. Know the difference between a lifestyle business and a category killer. Build a genuine support network.
By discarding traditional lock-ins, Mike turned a structural vulnerability into a company superpower. He built a powerhouse on trust earned daily, not legal traps. He is proof that self-imposed constraints become competitive advantages.
Kristin O’Neill • Team Canada & NY Sirens
Dominating professional women’s hockey on the world stage
Representing Team Canada on the ice, Kristin is a powerhouse forward dominating on the world stage. When the pandemic cancelled her senior collegiate season, she trained for the Olympics in her apartment using a hockey broomstick weighted down with cement blocks, ultimately scoring Canada’s first-ever shorthanded goal in an Olympic gold medal game.
The Principles: Kindness—make people feel heard and valued. Courage—say the dream out loud. Process over outcome—let preparation create confidence.
By discarding any room for excuses, Kristin let her character dictate her grueling work ethic when the world paused. She built an elite career on preparation, refusing to wait for perfect conditions to play big. She is proof that intensity and kindness are not mutually exclusive—and that preparation creates confidence when conditions are imperfect.
What Are You Not Sorry For?
We have enough vanity lists. This is a home for people whose principles make their ambition entirely defensible: built from Canada, open to the world, with no age limits, no pay-to-play, and no waiting for next year’s class or edition.
Name what you want. Know what guides you.
Then go pursue it without apology.
Every week, we profile three leaders who embody this standard. If your principles make your ambition worth championing, welcome.