I Asked 17 Successful Entrepreneur’s What Confidence Means To Them & The Role It Plays In Success (Including Their Own) – Here’s What They Had To Say

Whatever you can do, or dream you can, begin it. Boldness has genius, power, and magic in it.

I love that quote by Goethe and agree that boldness does have power.

There is power in being bold and taking action.

We all have a list of goals we’re hopefully for – ideas and dreams that we think about over and over again, that we badly want to get going on, to start creating.

The Doers & Non-Doers

While we all have goals, dreams, and ideas… not all of us act on them.

Why is that? 

Why are some people able to just take what seems like effortless action while others hesitate and hold back from moving forward?

Why this difference in people?

This is a question I’ve given lots of thought to over the past few years and came to a conclusion of what I believe the difference is between those who are bold and take action and those who hesitate and do not.



Confidence is what I concluded the difference to be between the action takers and the non-action takers.

But wait a second, isn’t confidence something anyone can develop?

I mean sure it comes more naturally to some versus others but still, it’s not like confidence is a gene or genetic trait like eye or hair color – it’s an attribute.

Some might even argue that confidence is a skill – OK fine.

But a skill is still something any one of us can learn right?


Here’s a  few more questions to consider regarding confidence:

Is confidence really a choice?

If it is, why do some people choose to be confident and others do not?

Better yet, why would anyone choose not to be confident?

If confidence is a skill, does that mean we can all learn to be confident?

Who would choose not to want to be confident?

Confidence is sexy and it feels good right?

If confidence is a choice and can be learned, what do we do and how do we start?


Confidence & Success

About a year ago, I reached out to 17 successful entrepreneur’s whose work I admire and respect and asked them all the following question….


What is your belief about confidence and the role it plays in being successful, including your own success?


Here’s what each one of them had to say…


Chris Guillebeau

B-q3gGrR_400x400The fear of regret has helped more than anything else.

I often ask myself, “If I have this idea and don’t follow through, how will I feel about it later?

When the answer is, “I know I’ll regret it if I didn’t try“, it’s much easier to muster the confidence to proceed.



Simon Sinek

simon-sinekWhen we discover our “Why“, we find the idea, cause or belief that inspires us to do what we do.

Our “Why” has to do about living in service to others. 

When we find the idea that is bigger than our own life that we wish to follow and contribute toward and lead, confidence no longer becomes the issue.

We now have the will because we have found the thing that matters even more than us. We have found our cause. We have found our calling.


Jonathan Fields

JonathanFieldsConfidence isn’t what got me where I am or where I’m going.

It’s much more about curiosity, gratitude, openness and a willingness to fail.

(I love this… “curiosity with a willingness to fail.”)



Benny Lewis

yuYh4csOMake a LOT of mistakes.

I aim to make at least two hundred mistakes a day, both in language learning and in business ventures.

This gives you a lot of learning opportunities. You fail your way to success much faster than if you prudently crawl your way there.


Chris Brogan

Chris-BroganMy confidence comes from trusting in my training.

The more I execute, the more I know I’m capable of doing what stands before me.

Because I spend time and effort taking on bigger challenges, increasing my capabilities and training constantly, I succeed. 


Elisa Blaha Cripe

6a00d8341c71c353ef01b7c7474159970bThe single most important factor that has helped me get where I am today is the ability to “think small“.

It’s sounds counter-productive, I know. “Don’t you need to think big to grow?” I don’t think so.

Thinking small has helped me to focus on just one step at a time.

Each step (be it a small business venture or creative project) has taught me something new and helped me develop better practices.

The skills I have obtained through each step have helped me gain confidence to try for the next thing…which of course leads to the next and the next.

I am so grateful that I didn’t worry about “the big picture” from day one and instead, set manageable, attainable goals.

Over the years, those little milestones have added up to a solid foundation for success.


Sean Ogle

Sean-Finely-Crafted-1-1200x648The single most important factor for building my confidence has been doing things even if I was scared, uncertain, or not sure how it’d workout.

Take that leap despite those concerns.

You quickly learn that it rarely turns out as bad as you think it might.

Things almost always workout better than anticipated, and once you have a few of those wins or experiences, it does wonders for your confidence and your ability to keep going bigger in the future.


Nicole Antoinette

Nicole-11Confidence is a funny thing.

It’s so easy to think that we can’t act and can’t succeed until we feel confident.

The single most important thing for me has been giving myself the daily reminder that I can do something hard/scary/uncomfortable even when I don’t feel ready.

You don’t need confidence in order to succeed – you just need to keep taking action and trust that eventually, confidence will show as a result of your action.


Tyler Tervooren

oQ_8pWqvI think everyone experiences a lack of confidence in their life at some point, no matter how dialed in we are.

There are two simple, psychologically proven tactics I use to help boost my confidence when I’m taking on something I might feel insecure about.

Here they are:

1) I look for evidence to prove me wrong. If I’m worried I won’t succeed at something, I look for evidence to suggest that I actually will.

That could mean looking at others’ successes and telling myself, “Yeah, I can do that, too.

Or, it could mean looking at other successes I’ve had and reminding myself, “I was unsure about that, but I made it work. Why should this be any different?

2) I take very small steps. Tiny, incremental wins help you really see what you can accomplish, and each one builds on the last to increase your confidence in the future.


Jenny Blake

OJMVBR0eConfidence doesn’t come first, it comes second (or last).

I almost never feel fully “confident” at the start of a big project or life leap.

It’s the baby steps that I commit to even without it, then building incrementally, that starts to give me a sense of momentum and possibility.


Scott Dinsmore

high-res-headshot-scottBy far the most powerful factor in battling fear and opening myself to possibility (and the confidence that comes with it) is surrounding myself with the right people.

The people around you will either kill your dreams or make them possible.

The beauty is, you get to decide who you hang around with.

For years I didn’t have a clue what was possible. So for 4 years my side project (I couldn’t call it a business at that point) grew by exactly zero percent.

Then I started to meet other people who had built the lives and business I couldn’t even really dream of before. And within six months things grew by 10x. In 12 more months they grew by another 160x.

Fast forward to today, a couple years later, and we now have in-person Live Your Legend communities in 150 cities in 48 countries and counting.

There’s no way that would have been possible without the right people in my corner to show me what was possible; supporting, encourage my ideas along the way. 


Chelsea Dinsmore

TDM_Team_Name1-190x190It was kind of a slow process for me.

Blogging for 3 years gave me the practice and confidence in cooking, writing, and putting things out there.

I then decided that I wanted to take things to the next level and almost quit before I even got started because I didn’t believe I could do it.

A food photography course (that was only $20.00 because I wasn’t willing to invest too much into something I wasn’t sure of) is where I saw the process of someone who does it in a very minimal way – cooks simply, takes great pics with very few props was the turning point for me.

I use to believe I needed more – better camera, proper lighting, etc. but realized that with a little help from Photoshop, I really could do it.

I’m not always super proud of every photo I publish but since I am in a constant learning phase, I think that will always be the case.

It’s better to get something out there rather than waiting for perfection.


Leah & Naz

Naz-and-Leah-Square[Leah] Being surrounded by people who believed in me and my abilities long before I believed in myself.

[Naz] Truly believing that I had something of real value to share with the world and I could actually powerfully share my talents in an impactful way. 



Jacqueline Carly

JacquelineThe single most important factor was when I realized that EVERYTHING is a choice, and that I am responsible for the outcomes in my life.

Even when circumstances happen that I don’t expect, I can choose how to react or not react.

There’s something empowering in taking ownership of that.

There will always be fear, resistance and struggles, but I can’t let that keep me from doing what I want to do. Life is for living now.


Ben Fanning

Fia-Ben-Fanning-0013-761A0797-1024x682My confidence comes from believing that what I have to offer will serve others.

Even in those moments when I’m feeling like what I’m creating isn’t 100% perfect or isn’t not good enough to share, I ask myself “can it serve others?

This always gives me the confidence to keep going.


Corbett Barr

Gk-J7-BCMy biggest confidence booster is always practice, and just producing a lot of work.

Whether it’s blogging or podcasting or recording videos or speaking on stage.

Practice, practice, practice is the key to feeling confident and doing my best work.


Alexis Meads

39fdb50Daily and consistent action is what helped me create the confidence necessary to get me to where I am today. 

I didn’t start out having a ton of confidence in myself, my work, and my ability to be successful.

But if you wait until you feel 100% confident, you’ll never make a move.

It’s taking a step, no matter how big or small, consistently that will get you to where you need to go and build your confidence over time.

I’ve been faced with indecision, fear, doubt and rejection. But the confident person moves forward even in the face of rejection and therefore gains more confidence.


Lessons Learned

This was an incredible learning experience for me and I am super grateful for each person here who took the time to respond and share with us their ideas and experience with confidence.

What I’ve learned from this experience and all of this incredible feedback is that focusing on developing confidence isn’t what creates confidence or success for that matter.

Confidence comes in the doing – in taking action.

Whether that’s taking small tiny steps, serving others, surrounding yourself it like-minded people who believe what you believe, making mistakes and learning from them, or just being curious.


The Message Is Clear…

Taking action isn’t a result of being confident.

Being confident is a result of taking action.


For years I had been looking through the wrong end of the telescope, thinking that as soon as I got my confidence up, I would get started on my dreams, my goals.

Maybe the same is true for you.

It’s time to change that and realize that the more we take action, the more confident we become.

Alexis Meads said it best, “if you wait until you feel 100% confident, you’ll never make a move.


Confidence Is Created When We Take Action

Whether it’s small actions as Elisa Blaha Cripe, Jenny Blake, and Tyler Tervooren suggest doing or imperfect action where we make mistakes, fail and keep moving forward as Jonathan Fields and Benny Lewis mentioned doing.

The key is to take action and keep moving forward.

That’s how we become more confident.

That’s how we become more successful.

Let’s stop thinking success is just for those who have the confidence to go for it.

If you take that last sentence and work it backwards… that’s what I’ve come to believe is the secret sauce to becoming more confident.


Go for It = Confidence = Success


Let’s commit to taking action on our goals and on or dreams knowing that when we do, we begin to develop enough confidence to take the next action, and then the next, and the next.

The person we become in the process as a result of taking action is what will make us successful.

The best way to gain self-confidence is to do what you’re afraid to do.

I use to be afraid of diving into deep water.

I decided in college I would no longer be afraid and decided to start jumping off of the diving board into the deep end of the pool (with floaties on of course). 🙂

I’m no longer afraid of diving into deep water (with no floaties either).

I use to be afraid of heights, so I decided to go Skydiving… twice.

I’m happy to say I am no longer afraid of heights.

I use to be afraid of public speaking, so I joined Toastmasters International.

After completing my 10 required speeches, I am no longer afraid of public speaking.

Running an ultra marathon (50 miles) sounds scary and overwhelming.

That’s a lot of miles!

I’m running my first ultra marathon this weekend, all 50 of those scary miles.

Am I scared? Absolutely.

But I know after I complete it (that really is a lot of miles)… the fear of running 50 miles will be gone.

It’s these experiences where I have taken action in the face of fear, when I didn’t feel confident, that’s given me confidence.

Confidence to chase my dreams, my goals, and all it is I want for myself, for others, and the world we live in.

So I ask you…


What Are You Afraid To Do?

What goals do you have that you’ve been telling yourself you’re not confident enough to go for?

Whatever they are, decide today to start taking action.

As small as that first step may be – begin taking action.

Small action, imperfect action, massive action, any action.

What matters is that you take action, begin moving.

It all begins with that all so important first step.

You don’t have to be confident, you just have to start.

You don’t have to be great, you just have to start.

You don’t need a ton of money or a bunch of different degrees, you just have to start.

Believe that you can, and you’re half way there.

Take that first step, and you will be there.

You’re awesome!



Leave a Reply

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

Contact Us

Give us a call or fill in the form below and we will contact you. We endeavor to answer all inquiries within 24 hours on business days.