4 Things That Will Boost Your Confidence as an Entrepreneur

Written By: Katie Caples

Chances are good that you’re feeling all the feels right now.

As a business owner, an employee, a human.

A student. A dreamer. A get-stuff-doner.

You started this year full of hope and enthusiasm. And now you’re full of overwhelm and anxiety.

Oh, and on top of it all, you are wading through a pandemic. A freaking pandemic. 


I’m here to reassure you. And to remind you that you are enough. 

Even as you struggle – especially as you struggle.

With each slow, intentional step forward.

You are the light.

“Slowing down is sometimes the best way to speed up.”

– Mike Vance

You are making progress. And as you take each step forward, you are hyperaware. 

You are mindful of the place you are in, with your family, your friends, your career. As you observe your day-to-day routines and dream your big dreams for your business and your future.

It’s exhausting and exhilarating.

Can I get a witness?

The changes you’ve experienced over the past six months have been drastic. 

You have adapted, adjusted, tried your hardest – well, most days. 

At times you feel like you’ve got this. And at times, well, you struggle.

Your emotions are all over the place

And yet you pivot. And pivot. And pivot again. 

Most importantly, you keep showing up. 

So how do you know you’re on the right track? 

Maybe you’re changing careers entirely. 

Maybe you’re at home with your little ones, wanting more out of your day. 

Maybe you’re growing your side hustle in hopes of quitting a job that no longer serves you.

Or maybe you are at a standstill.

My advice? Get out of your head. 

It’s time to roll up your sleeves and do a little soul searching. 

“As is our confidence, so is our capacity.”

– William Hazlitt

Let’s explore four ways to boost your entrepreneurial confidence.

1. Create a Pocket of Time for You – Time to Work ON Your Business, Instead of IN It. 

Time to pause, reflect, and recenter.

Because let’s face it, you’re learning and doing at a rapid pace. 

You sprint through parts of your learning, parts of your business. You put in the hours. You do the work. Or attempt to do the work, if you are anything like me.

Copy. Repeat. 

All while fighting off distractions.

At the end of the day, you’re tired, depleted. You have no energy to ponder open-ended questions. Or think through strategies. 

Instead, you muster up enough courage to post a question in the Facebook group. Or direct message a friend you’ve met through the course. 

Even when you know the next step to take. The hard step. Ugh.

So, you go, go, go, without much downtime. And what time you do carve out is for binge-watching your favorite series.

I mean, have you seen Scandal?

Protect these next few minutes with all your heart. Because they are for you. And for your business. But mostly for you.

“Follow effective action with quiet reflection. From the quiet reflection will come even more effective action.”

– Peter Drucker

Take a moment to pause, to stop consuming all the things. And instead, turn inward.

Consider this an invitation for quiet reflection.

Even if you feel good about your direction, your growth, your momentum, take a moment to focus, really focus, and reflect.

By doing so, you create space.

Think of it as closing all the tabs in your brain – yes, all of them. 

As you open a new document.

In this case, a fresh new page in your favorite journal or notebook. And grab a pen.

Settle in, take a few deep breaths to center yourself. 

And intentionally remember these words from our favorite course-creator and mentor.

“Act like a business owner, not a freelancer looking for the next gig.”

– Sarah Turner

2. So Much Good. Jot Down Something Positive That Happened in Your Business Last Month – Or, Even Better, Last Week. Be Specific.

This will get you to a place of positivity, a place of strength and gratitude.

Maybe you learned something new that clicked. Maybe you had someone say something encouraging to you. Or maybe you felt like your mentor online was speaking directly to you.

Did you find a new podcast that’s serving you well, take a baby step in starting your business, gain a specific client, or create a piece of content that resonated with your ideal customer?

Do not overthink it. And do not skip this step.

“It’s easy to forget to catch yourself doing something right.”

– Jeff Olson

Take a moment to take inventory of the good in your life. 

And catch yourself doing something right. 

Go ahead, jot down something good. Maybe even two things.

3. Picture Your Favorite Customer. Describe Him or Her. List How You Served Him or Her. And Include All the Things You Appreciate.

This will center you. It will give you clarity. 

Take a moment and mentally scroll through all the people you’ve served.

Those you’ve helped in some way. Picture their names and faces.

As you visualize your favorite customer, think about how that person makes you feel in your interactions. And how you make him or her feel in return.

Think about the variety of products she buys from you. 

The tone he uses in his response to you. 

Or how when you work on that project, you’re at your best creatively.

If you don’t have a favorite customer yet – no worries. 

Dream him or her up right now. 

Create an avatar, give him or her a name, and jot down characteristics, including how you’ll work together.

Take a moment to stretch yourself here.

“I’ve learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” 

– Maya Angelou

Start thinking about how you can attract more of your favorite customers. 

Let it simmer in the back of your mind as you continue reflecting. As you go about your learning.

And be sure to jot down any random ideas. Keep a notebook nearby and send yourself an email when inspiration strikes.

4. Name Your Frustrations. The Things That Drag You Down, Those Things You Wish You Could Improve. Think About Money, Marketing, Processes, and Time Wasted.

Ok, so things are not all rainbows and unicorns. Especially now.

Hello, 2020. 

With that in mind, create a list of the things that keep you up at night, the things that stall your forward progress, and the things that bog you down.

Your list may be all over the place. 

Just go with it.

And be specific here, too.

Maybe your administrative tasks weigh you down. Or maybe your frustrations come from content creation or accounting functions. If your sales have slowed or dried up, this is the place to release your emotions.

Are distractions a big hurdle for you?

As you jot down all the things, look for themes. 

Create buckets or symbols for things that are similar. 

Right now, at this moment, you do not need to come up with strategic solutions. This exercise is to increase your awareness.

“Awareness is the greatest agent for change.”

– Eckhart Tolle

It’s important to know where you get bogged down, whether you’re brand new to the course or you’re an experienced copywriter.  

And if you have tasks that you dislike, like really dislike, now is the time to name them. 

Maybe, just maybe, you can offload them as your business grows. 

For now, you are simply identifying these tasks. And please know, it is okay not to love – or gasp, even like – each and every aspect of running your business. 

It is quite okay if you dislike a certain type of writing – be it blogs, email campaigns, web pages, etc. Or any other part.

There isn’t an entrepreneur out there that loves each aspect of his or her business. 

It’s about making intentional steps forward.

One decision at a time

Maybe the next step for you is a 20-minute conversation with a peer.

Or a solid hour to research a challenge and outline a solution.

Whatever it is, just be sure to put it in your calendar.

Cultivate Your Entrepreneurial Mindset.

With these reflections, I hope you find clarity.

And I hope you gain confidence.

Because you are a bad-ass business owner. 

And you know, deep in your gut, that you’re going to make this work.

“The best way to predict your future is to create it.”

– Abraham Lincoln


Look, I get it. I’m walking this walk with you. I’m trying to pivot my in-person workshop business in a direction that makes sense. While I raise my babies (hello, virtual schooling), tend to my farm, and wear the many hats we all wear. 

My hope for you, and me, is to extend grace – to yourself and those around you. As you go about your life and dream your big, audacious dreams.

As a bonus, here are my top three books on business. It includes the title, author, a quick description, and my favorite quote from the book.

These books will inspire you as you follow your dreams and refine your business.  

  1. The Slight Edge by Jeff Olson

Sarah raves about this book, for good reason. I read it years ago as I was growing my career in the nonprofit sector. And this second time, it was even more powerful. 

“I believe we are here to learn and grow, and to become so abundant in belief in ourselves that we finally tap into the full potential of the greatness that is within us and share that greatness with the world.”

  1. Everything is Figureoutable by Marie Forleo

This is such a good motto in life and business, and Marie drops nuggets of wisdom that are pure gold. It’s an easy read and best of all, it’s full of practical tips and actionable steps.

“What we say to ourselves in the privacy of our own mind matters.”

  1. The 15 Invaluable Laws of Growth by John Maxwell

John is the godfather of personal development. I highly recommend all of his books, but this one tops my list. Plus, it’s super easy to read. So there’s that.

“Learning to pause allows growth to catch up with you.”

Find them wherever books are sold.

Happy reflecting. And reading. And doing.

Sending you all the good vibes as you continue in your journey to freedom.

We are in this together.


This is a guest post blog written by Katie Caples, author, coach, and Write Your Way to Freedom alum. In her latest book, Courage: A Journal to Explore Your Bold, Brave Spirit, she creates space for women to grow through self-reflection.

About Sarah

I’m an entrepreneur on a mission to help other people become entrepreneurs.
My blog is a place where I provide business building advice and explore how we can create more meaningful work.

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