Courage Over Confidence: Lessons from Reagan Cannon on Leadership and Entrepreneurship
Reagan Cannon
When we think about leadership, many of us envision someone walking into a room brimming with confidence. But Reagan Cannon, a former Amazon executive turned leadership speaker and coach, flipped the script in our latest podcast episode. She shared a truth that every badass woman in business needs to hear: confidence doesn’t lead to action—courage does.
Reagan’s journey from corporate to entrepreneurship is a masterclass in redefining success. After 20+ years of leading massive teams and crushing goals at Fortune 15 companies, she did something many of us only dream of—she left it all behind to build something on her own. Was it scary? Absolutely. Did she wait until she felt fully ready? Nope. Reagan didn’t wait for confidence to show up. She showed up with courage, and that made all the difference.
Why Courage Beats Confidence
Here’s the game-changing lesson: confidence is a byproduct of courage. Reagan explained how so many women are stuck waiting—waiting to feel confident enough, waiting for the right time, waiting for someone to validate them. But courage doesn’t wait. It acts. And every courageous step you take builds the confidence you’re longing for.
Whether it’s applying for a promotion, speaking up in a boardroom, or launching your own business, courage is what moves you forward. Reagan’s mantra? “Confidence is an emotion. Courage is an action.”
Overcoming the "Competence Complex"
One of the standout moments from the episode was Reagan’s deep dive into what she calls the “competence complex.” Many women feel like they need to know everything about everything before they can take on anything. Sound familiar? It’s the reason we keep signing up for more degrees, certifications, or training when, in reality, we’re already capable.
Reagan’s advice: stop waiting for permission. You are credible right now.
Relational Courage: The Game-Changer for Women Leaders
Reagan’s research into relational courage highlighted another critical piece of the puzzle. Women are often socialized to “be good” and avoid rocking the boat. This mindset works at entry-level positions but becomes a career blocker at senior levels. To lead effectively, we need to challenge the status quo, share our strategic insights, and confidently advocate for ourselves and others.
This is where relational courage comes into play—building the guts to speak up, make bold decisions, and form meaningful connections with mentors and peers.
Experimentation Over Perfection
Another powerful takeaway was Reagan’s embrace of experimentation. Coming from Amazon, where billion-dollar failures are seen as learning opportunities, she learned to ditch the perfection mindset. Instead, she approached entrepreneurship with curiosity and calculated risks, a strategy she calls the “Monster Audit.”
Here’s how it works:
List the worst-case scenarios of any decision.
Rate each scenario by severity and likelihood.
Multiply those scores to calculate the actual risk.
Spoiler alert: most of the fears holding us back are low-risk when you break them down.
Reagan’s Challenge to Women Everywhere
Reagan left us with a challenge: stop holding back. Your ideas, your voice, your presence—they matter. But waiting for the perfect moment, the perfect plan, or the perfect confidence will only keep you stuck.
“Sometimes you just have to take the leap,” Reagan said. “You don’t need confidence to do it; you need courage.”
Final Thoughts
Reagan’s story is a reminder that greatness doesn’t come from playing it safe. It comes from stepping into the unknown with courage, trusting that the lessons you’ll learn will be worth it. Whether you’re climbing the corporate ladder, running your own business, or dreaming of making the leap, Reagan’s message is clear: take the risk, make the move, and own your brilliance.
Want more wisdom from Reagan Cannon? Check out her website and blog, The Eight Things I Learned About Entrepreneurship, at ReaganCannon.com.
Stay courageous, stay badass, and stay tuned for more stories that inspire and empower!
