Have you ever wondered what really separates extraordinary leaders and entrepreneurs from the rest?
I’ve been on my own journey to answer that, and my conversation with Dana Theus and Shirley Engelmeier (two unstoppable forces in leadership and inclusion) knocked me sideways with insight.
There’s a through-line in courageous leadership that’s rarely discussed, and it isn’t about inspiration, charisma, or mastering some secret “success formula.”
It’s about patterns.
Let’s dig into the patterns that transform not just your results but your experience of being a leader who is unapologetically YOU.
It’s Never the One Big Move (It’s the Habit You Build)
When most people talk about courage, they picture that one bold moment: The CEO who speaks up, or the founder who bets it all.
But as Dana put it:
“It’s not any single act of courage. It’s about the PATTERN of courage over time.”
That lands, right? The leaders making the greatest, most lasting difference aren’t just out here swinging for the fences one time; they’re consistently choosing courage.
Here’s what I’m seeing (and maybe you’ll find yourself in this list too):
- The founder who sends the pitch email despite the fear of rejection.
- The coach who raises rates (clients be damned).
- The creator who launches the program before it’s “ready.”
Every time, the choice is just another line added to the pattern of who you’re becoming.
“Courage isn’t a one-time act, it’s a pattern you build, every single day.”
What might change for you if you focused on building a streak of small, courageous choices, instead of waiting for that mythical ‘big’ one?
What Game Are You Playing, Really?
Another gem that came out of our roundtable:
How many of us are playing by rules we didn’t write, in games we never even chose?
Before Outlier’s Edge, I was part of the “3% club”, one of a handful of Black males in consulting firms coast to coast.
Here’s the kicker:
I didn’t leave that game because I couldn’t win. I left because even winning wouldn’t have delivered what I actually wanted.
Are you pouring everything into winning someone else’s game?
I see it with clients all the time:
- The consultant “crushing it” by everyone else’s standards, but exhausted by a model that isn’t their own.
- The exec with the title, but no joy.
- The agency owner growing revenue, but dying inside.
Maybe the question isn’t how do I win…but am I playing the right game for me in the first place?
“The most extraordinary outliers I know aren’t just good at playing the game they’ve chosen to play a different game entirely.”
So what about you? What game are you ACTUALLY playing? And does it fit who you are when no one else is watching?
Breaking Down Courage, Because “Be Brave” is Terrible Advice
Shirley spoke some serious truth:
“Courage can be a really fluffy adjective. Leaders are terrified right now. But…if you break it down into observable steps, courage will be the result.”
How much time (and wasted energy) do we lose telling ourselves to “be courageous”, without a single clue how?
It’s like telling somebody to “be successful.” Uh…how?
Let’s make it actionable:
- Pinpoint exactly what feels risky.
- Map out the smallest steps possible toward it.
- Focus on the very next step, not the full mile.
When you systematize courage, it stops being a mystical quality and starts being something you can practice, repeat, and get better at.
“What if courage isn’t something you need to find, but something that emerges naturally when you have the right roadmap?”
If you’re stuck in “waiting mode,” shift your focus to building the system that makes courage inevitable.
The Hidden Question: What Feeds Your Soul?
Here’s a question that flipped Shirley’s entire business:
“What am I passionate about that I can pour into?”
(Ever asked yourself that lately?)
Because here’s what I noticed in my own journey: The projects that feed my soul are the same ones that create the deepest impact for others.
But nobody asks us, “What would your business look like if you built it around what really lights you up?” Instead, it’s “What will sell?” followed by “How much?”
What if you dared to ask the first question for once?
“What feeds my soul that I can pour into the world?”
This is the real path to alignment—and the sustainable business that actually means something.
The Invisible Advantage: Be Yourself, Fully
Maybe the deepest insight from this conversation is this:
Dana said,
“When you just show up and be who you are, something invisible gets created between other people who are doing the same thing.”
I watched this unfold live. The moment we dropped the performing and leaned into authenticity, everything changed. That’s when the wisdom, energy, and real connection happened.
High-performing entrepreneurs and leaders get this:
Their edge doesn’t come from copying the market. Their breakthrough comes from finally, unapologetically leveraging their own quirks and strengths.
Where might you be diluting yourself? What might happen if you stopped hiding—and leaned all the way in?
“Model the future in the present—authentic action inspires real impact.”
Bringing It All Together
Patterns. Games. Soul. Authenticity.
This is the intersection where real impact gets made.
- You don’t need to wait for courage. Build a pattern of it.
- You don’t have to master the rulebook. Ask, is this my game?
- You don’t have to chase someone else’s definition of success. Ask, what feeds my soul?
- You don’t have to hide. Your difference is your advantage.
If you’re feeling the tension between where you are and where you feel called to be…
If you know it’s time to design your OWN rules, create a system for authentic courage, and align your work with what energizes you most—
Now’s the moment.
Journey On,
Niiamah
P.S. – If you want to dig further into your pattern of courage, your hidden strengths, or your next business game, this is the space for it. Reply below or reach out for one of my open Strategy Roadmap Sessions. Let’s design the courageous, fulfilling, authentic game you’re meant to play.
What came up for you reading this? Where are you noticing a ‘pattern of courage’ (or the lack of it) in your journey right now? Drop your thoughts below, I read every one.