How To Know If You're A Courageous Entrepreneur (3 questions to ask and keep asking)
Sep 01, 2025
Am I brave enough to be a “real” entrepreneur? Do I have what it takes? Can I really do this?
Do any of these sound familiar?
“Courage is a major part of being a business owner. You have to
have courage to get into the arena of doing business.” Kim White
The good news is that if you started the entrepreneurial adventure, it means you do have courage!
But it’s not just about starting a business.
It’s also not just about maintaining a business.
You want to build a business that allows you to live the life you want.
It takes courage to build a business that you own, and that doesn’t own you.
Here are 3 questions to ask (and keep asking) yourself on the entrepreneurial adventure to stay courageous as you grow your business.
Are You Balancing the Messy and Meticulous?
" There's no workman whatsoever he be, that may both work well and hastily. " Geoffrey Chaucer
If you're moving at a quick speed, that usually comes with the sacrifice of accuracy. And if you're moving at a meticulous pace, that comes at a cost of speed.
You have to have the courage to look at your business and make a call. Which is more important: speed or accuracy? Be honest.
And then literally follow that without getting caught up in the other one. That’s the part where you need to have courage.
Realistically, if it's a speed thing, there might be some accuracy issues. And that’s okay. And if you have the kind of business where you need to be meticulous and things need to be perfect, you will have to work slower. And that’s okay.
“We do believe messy is beautiful. When you're getting started, it can be messy, but sloppy is not beautiful.” Kim White
When you are trying to go too fast and you're making a mess of things, that's different than getting started in a messy way.
“Messy is okay to a point. But we don’t want to scale our mess. We have to learn the technique, and not just carry on in the messy way we got started.” Jill Olish
Courage Challenge #21 is to look at your business and decide where you need to focus on speed and where to focus on accuracy. Both are important, but you can't have both all the time.
“You have to know which is more important so you can honor the commitment you’re making.” Kim White
Do You Have The Right Mentor?
In the movie A Knight’s Tale, William’s dad allows him to go across the big pond to live with a knight and start his adventure of changing his stars.
" He's a real knight, William. Watch and learn." A Knight’s Tale
William’s dad knew that if his son was ever going to change his stars and become a knight, he would need to learn everything he could from a real knight.
That is the kind of perspective you need when you’re looking for a mentor on your business adventure.
It’s natural to look for a mentor who will just tell you what you want to hear. But that’s not a mentor. A mentor will be honest with you and tell you the hard things that you need to hear.
Look for someone who will get you through those hard times in business. Someone who will show you the way to learn the techniques you need. And will point out where you might need to grow as a human.
Being open to just anyone being your mentor is a problem.
“Take opportunities you get to find someone who has experience and understanding of humans and business. Someone that has done some things that you’re looking to do.” Kim White
Courage Challenge #22 is to think about the kind of mentor you need. Who do you have the courage to let mentor you?
“It takes a long time and a lot of courage to find the right one. Don't give up. Don't stop short of finding someone who's really going to get you through the hard stuff.” Kim White
Do You Remember Your Roots?
As William says goodbye to his dad, he calls out to him as he sails away on the boat, “I’m afraid I won’t know the way back home.”
And his dad says, “Just follow your feet!”
It was an encouragement to him to know that, no matter what, he would be able to find his way back home.
“When he said follow your feet, I immediately translated it to follow your heart. You walk with your feet, but it's actually your heart that directs you.” Kim White
Remembering your roots, where you came from, is what will direct your heart on the business adventure.
Your roots can give you confidence when you know that you have overcome them or upleveled from them.
“That goes along also with our ‘why’. We never forget why we're doing something. And most times our why comes because of our roots.” Jill Olish
Knowing your 'why' is really important. It is empowering. If you don’t know what your ‘why’ is, then have the courage to keep going and find it.
Not everybody's proud of where they came from.
“I remember what it’s like to not have enough. I don’t ever want to forget that.” Kim White
Courage challenge #23: Where did you come from? What do you need to remember? Do you need to get back to where you came from?
A lot of times, you need courage to look back and answer those kinds of questions.
When you have the courage to ask the right questions, it keeps your business growing in the right direction.
You will be building a business that you own, and doesn’t own you. That’s the dream. But it takes courage to get there and to stay there.
So keep asking these three questions on your entrepreneurial adventure, and you will be able to know for certain that you are a courageous entrepreneur.
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 courageous 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!
