How To Be Courageous Enough To Do Business Differently
Aug 18, 2025
What does the movie A Knight’s Tale have to do with running a business?
“There are so many surprising correlations between the movie and the courage it takes to do a lot of things in business.” Jill Olish
It’s time to zoom in on one entertaining scene that has 4 meaningful courage challenges for entrepreneurs.
So get your movie snacks, and rewind to the scene where William is given his new armor by Kate, the female blacksmith with some innovative ideas.
Have The Courage To Brand Your Unique Thing
When Kate, the blacksmith, makes the new armor for William, she makes a mark on it to claim it as her own design.
“They’re the marks of my trade, should another knight admire the armor.” A Knight’s Tale
She created a unique kind of armor that had never been seen before, and she marked it, branding it. That took courage.
Sometimes in business, there is a new way of doing things. You need to have courage to do it, and then you need to have courage to be proud to put your name on it.
Courage challenge #17 is to figure out what you are going to brand. What are you doing differently from others in your area of business? Are you going to have the courage to put your name to that and brand it?
Have The Courage To Put Your Business To The Test
It took some convincing, but William finally agreed to put the armor on. But there is one more thing he has to do before wearing it to the jousting tournament. He needs to test it.
And that takes courage because he could get seriously hurt if the armor isn’t as strong as it needs to be.
Did you notice that he wasn't alone when he tested the armor? He had his friends and his crew with him. He knew they had his back. They wanted to make sure he had the strongest armor possible, but they also didn’t want to hurt him in the testing process.
And that’s a lesson for business, too. The entrepreneur adventure is always better together.
“We don't have to be alone when we are testing out our things, and we can have those who are in our corner be the ones to test those things with us.” Jill Olish
Courage challenge #18 is to ask yourself: What do you need the courage to test in your business? Also, consider who you’ll ask to help you with the testing process.
Have The Courage To Be Laughed At
While William is testing this new armor, everyone laughs at him because of its strange design. It was something they’d never seen before. And William had to have the courage to practice with his new armor while being laughed at.
When you’re on the entrepreneurial adventure and you’re doing something new or different, like trying on the new armor, be prepared for the haters to laugh at you.
“This is very hard for all of us humans, but it is something that will happen when you're doing something new or different.” Kim White
Courage challenge #19 is to think about the area in your business where you need courage to allow someone to laugh at you.
And remember that when your way works, you will get the laugh in the end.
Have The Courage To Care
William is about to joust in his new armor for the first time, and before he takes off, he asks his friend about his opponent. His friend whispers in his ear, " His people starve while he sits at Banquet."
And because William has a heart for the people, that line gives him the motivation to knock his opponent right off his horse!
For context, jousting was only for men of noble birth. By default, those men were leaders in their cities and towns. The way they governed was reflected in their reputations.
As a business owner, you’re a leader. And there are times to ask yourself, “Do you sit at Banquet while your people starve?” In other words, are you taking advantage of your clients and customers to make more money for yourself and not thinking of them too?
Are you charging something that is so far beyond the people who need what you have that they can't even do business with you? Would it hurt you to be a little more reasonable?
“Your time is valuable, and you are not responsible for everyone in the world. But what are you doing to do good business?” Kim White
If you have a business and you are struggling to get or keep clients or customers, could it be that you need to reevaluate what you’re doing and what you’re charging?
“We can sometimes get caught up in all of these services we offer to our clients, and how much they pay us. But how are we showing up to honor that? We must have the courage to be honest with what load we can handle. Are we living up to the expectation of what we've put out for services?” Jill Olish
Courage challenge #20 is to assess whether your clients and customers are starving while you're feasting. If they are, you need to have the courage to do something different.
When you’re doing things differently, there are going to be haters, and it’s going to be tough. But it’s an opportunity to get courageous so keep doing these courage challenges on your entrepreneurial adventure.
“We can get locked up in the idea that there's already someone doing it, without understanding that people are coming to find us because they like us and trust us. That's where we get more of that courage to keep doing what we're doing.” Jill Olish
No matter what problem your business solves, you need courage to keep showing up and bringing your solution to the people who need it.
If you missed the conversation about this between Kim and Jill on their podcast Buckets and Boom Gates, you can catch it here.
Our Groundwork Brigade is a home for entrepreneurs who want to build a business that they own and that doesn't own them. It’s a community of like-minded entrepreneurs finding freedom in the entrepreneurial adventure by practicing putting the right things in the right order.
It’s a safe space to learn how to build a relational business using irresistible marketing strategies, tailored to your individual needs, in a group setting, with lots of accountability and support.
To connect and find out more about Kim or how to create a sexy business for a sexy life, you can reach her and the My Sexy Business Team at www.mysexybusiness.com.
And to connect with Jill Olish go straight to her website www.mamaoutspoken.com and you’ll find her there!
