15 Entrepreneurs Explain What Being Bold Means to Them

The definition of boldness differs with each individual. To some, it’s being authentic and transparent in the face of crisis while to others it’s just the state of being different. We asked entrepreneurs and business owners their definition of boldness and here are the insightful responses.

#1- Rolling the dice

Photo Credit: Catherine Moolenschot

It's spending that money on X marketing activity when the outcome is uncertain – it could definitely bring in good leads but… what if it doesn't? Be bold. Roll the dice. Implement and experiment until you find something that works. Being bold means constantly looking for ways to grow and improve. It means being bold enough to say ‘Here I am, this is what I do, and this is how I can help you'. It means doing what scares you.

Thanks to Catherine Moolenschot

#2- Being fearless

Photo Credit: Jeff Arnett

A bold individual can take risks and chances without hesitation. When someone is bold, they are always noticed in a room. They stand out from the rest because they show such confidence, can be outspoken and are more willing to take on new projects and responsibilities. They speak their mind and are not afraid to do so which makes others more interested to hear their point of view. Bold people are motivated which encourages others to stay motivated therefore they are exciting to be around. Every team needs bold individuals!

Thanks to Jeff Arnett, Arnett Designs!

#3-Stepping outside your comfort zone

Photo Credit: Joy Symonds

I have found that challenging my assumptions about other people’s reactions can result in a happy success. Being bold also means thinking big about your market. In the past, I drew an imaginary line for our market based on past performance, population and our competitors’ locations. But over the past year, we have brought in more and more customers from outside that imaginary line. Results have forced me to think creatively about how to reach more of those customers who will drive right past their local funeral home to use our family-owned firm with five-star reviews.

Thanks to Joy Symonds, Symonds-Madison Funeral Home!

#4- Embracing who you are

Photo Credit: Debra Eckerling

Put simply, being bold means embracing who you are – your strengths, talents, uniqueness – and living life as your most authentic, happy self. To do that, you need to first take the time to figure out what it is you actually want – is it to build your business, become a known expert, or achieve work-life balance? – and then put a plan in place to make it happen. Whenever you are invested in something that makes you happy – whether it's a full-time business, a side hustle, or creative project – your enthusiasm and boldness will show in all you do.

Thanks to Debra Eckerling, The D*E*B Method!

#5- Pushing the envelope every day

Photo Credit: Seth Bader

I’ve been practicing law for the past 15 years and as I’ve moved up the ranks from being an associate attorney to managing attorney in my own law firm, I’ve come to know that being bold means pushing the envelope every day whether at work or at home. Our clients depend on us to find solutions on how they can receive the best medical treatment and maximum compensation under the law. This means that we can’t be limited by boundaries or become too complacent with our situation. There’s no room for staying in the comfort zone because we have to go farther than what we’ve set our sights on to deliver success for every client.

Thanks to Seth Bader, Bader Scott Injury Lawyers!

#6- Unapologetic

Photo Credit: Dre Baldwin

Bold means to be unapologetic. Going after what you want intentionally and without hesitation. Knowing that there is risk involved, but not allowing that to slow you down as it does to most people.

Thanks to Dre Baldwin, The Mirror Of Motivation!

#7- Two things

Photo Credit: Liz Jeneault

I define being bold as taking chances and not letting your own insecurities or lack of confidence hold you back! A bold person knows what they bring to the table and they are not afraid to share their ideas with others. They're willing to take chances, as they understand that risk often comes with great reward.

Thanks to Liz Jeneault, Faveable!

#8- Not reckless

Photo Credit: John Moss

Recklessness means making a choice or taking an action without determining the potential chances of success or weighing up the risk versus reward benefit first. Recklessness might also mean knowingly gambling or making decisions where the odds are stacked against you and the chances of the gamble paying off are very slim, and the consequences of this very serious; like spending all of the business's liquid funds on lottery tickets instead of paying staff salaries, hoping to get a win that'll cover the salaries and leave the business in profit too!

Thanks to John Moss, English Blinds!

#9- Mindset

Photo Credit: Angela Hope

It's not so much about the actions that you take every day in multiple situations, but about your thought patterns, and how you choose to execute those thoughts and plans. You don't have to be born bold. You can learn to be bold by thinking brave thoughts and leading others to do so by example.

Thanks to Angela Hope, Upflip!

#10- Being a CEO

Photo Credit: Andrea Loubier

The simple fact that you're a CEO means that you're bold. And if you're a founder or an entrepreneur, you can multiply that by about a hundred. Stepping out into the unknown to start your own company can be scary, intimidating and even overwhelming. But at the end of the day, you can stand on your own two feet and feel brave and yes, very bold.

Thanks to Andrea Loubier, Mailbird!

#11- Taking chances

Photo Credit: Robyn Flint

It is going for what you want and putting in the work to make it happen. Boldness means speaking when no one else will and advocating for those who can’t advocate for themselves. Bold is taking initiative and not being afraid to fail. It is taking failure and turning it into opportunity. A bold individual doesn’t wait for opportunity to knock but invites opportunity every day. Being called Bold is a compliment and one that I strive for daily.

Thanks to Robyn Flint,!

#12- Not running with the herd

Photo Credit: Cindy Harvey

Being bold is all about choosing to follow your own path and build your business in a way that feels right to you. There’s so much noise, many opinions, and ‘do it this way’ points of view out there that it can be easy to get swept up in the wave. Opting not to run with the herd may be the road less travelled. Having done it both ways, I’ve learned that while following the pack may bring short-term gains, it can end up building a business that’s out of alignment. And having a business that isn’t a clear reflection of who you are will only get you so far. Be bold by following your instincts and building your business your way.

Thanks to Cindy Harvey, Cindy Harvey Career Coaching!

#13- Logic, expertise and passion

Photo Credit: Maddie Kluska

It takes a certain level of confidence and knowledge to be bold in the business world. There will always be people who disagree with your methods, opinions or ideas, but as an entrepreneur, you need to trust in your skills and push for what’s right for your company. However, it isn’t just standing up for what’s best for your business, it’s also about sparking innovation in your industry. Sometimes people are bold for the sake of being bold, which is never the right fit for the business world. If someone has more expertise in an area of business than you, it’s important to consider their advice. Just remember that boldness is filled with logic, expertise and passion. If there is reason and innovation to the risks you take, then they are always risks worth taking.

Thanks to Maddie Kluska, Positive Venture Group!

#14- Acting as a trailblazer

Photo Credit: Deborah Sweeney

I love the phrase ‘Fortune favors the bold.' I think it perfectly sums up how I would define being bold. There's an element of risk involved for sure, but great things happen to individuals that make the choice to take that risk and try something new. Being bold means you are acting as a trailblazer. You are carving out a path for yourself, which might not have been established before. There will be challenges and opportunities ahead, but you will have the confidence to keep moving ahead.

Thanks to Deborah Sweeney,!

#15- Three things

Photo Credit: Dean Calhoun

As a Founder/CEO of a small company, being bold can take many forms; which can include the following: 1) making decisions or choosing a direction under conditions of extreme risk and reward. Often, much like a skilled poker player, it relies less on hard data and more on your “gut” feeling; 2) making decisions that are counter to the popular or “safe direction; and, finally 3) being bold involves setting goals for your company and yourself that are not easily obtainable. These are much more than just stretch goals, but are goals that will take a significant change in approach or thinking.

Thanks to Dean Calhoun, Affygility Solutions!

How would you define being bold? Tell us in the comments below. Don’t forget to join our #IamCEO Community.

Mercy - CBNation

This is a post from a CBNation writer. CBNation is a Business to Business (B2B) Brand focusing on increasing the visibility of and providing resources for CEOs, entrepreneurs and business owners. CBNation consists of blogs(, podcasts ( and videos ( CBNation is proudly powered by Blue 16 Media.

Related Articles

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Back to top button