4 Practical Ways Courageous Entrepreneurs Prepare For The Tough Times
Nov 03, 2025
Any adventure is fun while the sun is shining, the breeze is cool, and your snack bag is full. But when those clouds start gathering, it’s getting stormy, and your tummy is growling, it’s easy to wish the adventure away.
The entrepreneurial adventure is exactly the same.
When everything is running smoothly, it can be great being your own boss, making your own decisions, and choosing your hours.
But when the tough times come, whatever they may be, it’s easy to throw in the towel and give up on your business and the freedom it brings to your life.
Those tough times are coming whether you like it or not. The secret to getting through them is how you’ve prepared for them.
Here are 4 lessons from one scene in the movie, A Knight’s Tale, that will challenge you to prepare courageously for the tough times ahead on your entrepreneurial journey.
1. Relationships: Quality over Quantity
William eventually gets caught for impersonating a knight, and he is locked in the stocks in the town square. He can't move or get away, and people from the crowd are throwing rotten fruit at him and taunting him.
But the beautiful thing is that his loyal friends are protecting him. They are literally standing in front of him and taking the rotten tomato hits for him.
When you build the right kind of relationships, you are building a firewall for the future.
There will be times in the future when you aren’t able to fight back or stand up for yourself, and you’ll need that relationship-layer of protection around you.
“That's a testament to building relationships. And it takes courage to trust other humans.” Kim White
Courage Challenge #33: What courage is it going to take for you to trust others to come alongside you in this business adventure?
2. Allow Yourself To Be Knighted
There is another beautiful moment in this scene from the stocks. Somebody steps in that makes the noisy crowd stop all their taunting and tomato throwing. It’s royalty. He steps in to change William’s stars out loud, and on paper, and it cannot be refuted.
He knights William in front of everyone in the town square.
All William has to do is accept. He needs to have the courage to accept the title, and the responsibility that comes with it.
Courage Challenge #34: Could you allow yourself to be “knighted” like William? Do you have the courage to accept an honorary title and role from someone you consider to be royalty in the entrepreneur world?

3. Find Your Flavor
" Your men love you. If I knew nothing of you, that would be enough, but you also tilt when you should withdraw.” A Knight’s Tale
Before he knights William, the prince looks at him and sees two things.
He sees his team protecting him from the crowd. And he recognizes the fierceness in him to stand firm and not run.
On the business adventure you must learn to recognize in others the qualities that you respect and look up to. That’s the kind of community you need to build.
“It’s not just about having any community, but finding the one that fits with what you know you want to do in your business.” Jill Olish
They need to be your flavor.
Courage Challenge #35: Do you have the courage to surround yourself with those kinds of humans based on the evidence that you're gathering?
“We surround ourselves with people who have the same drivenness and want to continue to move forward in things.” Jill Olish
4. Be Kind To All
" If I may repay the kindness you once showed me. Take a knee… I knight you, Sir William.” A Knight’s Tale
This particular royal tried to hide his identity so that he could participate in jousting because if they knew his position, other knights would have to surrender, and that would have revealed the prince’s identity.
But William did not surrender. He didn’t give away the prince’s identity. He competed against him and won. And the prince appreciated that he was able to compete as a “regular” man.
He appreciated that kindness so much that he gave that as the reason for knighting William.
“You never know who you are dealing with.” Kim White
You never know, when you're dealing with someone, who they really are. So be careful how you treat people.
Courage Challenge #36: Are you treating people well? Even the people who can’t do business with you right now. Are you being kind to them? Because it matters.
“They may refer you because of your kindness.” Kim White
Or they may turn around later when the timing is right for their business and want to work with you because of the relationship you’ve built.
Be brave.
Have the courage to take the time to prepare for the tough days down the line. You never know when they’re coming and what they will look like.
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!