Overcome entrepreneur mindset barriers: 16 Successful business owners share how they did it

Having the right entrepreneur mindset is essential to the success of your business. Find out how 16 successful entrepreneurs overcame their mindset barriers to build a successful business.

“Starting a business is like preparing for war.” – Josh Dorkin, Founder of Bigger Pockets

Have you ever felt that way?

As amazing as the benefits of building a successful business can be, make no mistake about it, the journey is rarely one that’s only filled with meadows of roses, sunshine, and rainbows.

There are many battles you have to fight when it comes to building your business.

There are challenges like knowing how to get started, where to find clients, or even how to not let social media suck hours of your life away each day.

But honestly, those obstacles are nothing when compared to the battles that go on in your head.

And it’s how you respond to those pesky mental barriers, that ultimately will determine your level of success as an entrepreneur.

As ever present as those mental hurdles seem to be in the life of an entrepreneur, they rarely get talked about.  At least not publicly anyway.

That’s because talking about things like imposter syndrome, fears, and wrong-thinking isn’t sexy.

But if most of us knew that the mindsets that limit our success were not unique to us, we’d be more comfortable talking about them so we could get free of them more quickly.

So that’s what we’re going to do today.

I asked a number of successful entrepreneurs a simple question:

What was the biggest barrier in mindset that limited your success as an entrepreneur and how did you overcome it?

They were brave enough to openly share the struggles they have experienced in their journeys.  And fortunately, they were also able to highlight how they overcame those barriers to build the thriving businesses they have today.

What I found most interesting as I read through the responses, was the thread of familiarity that ran through each business owner’s experience.  Multi-millionaires with tons of exposure have had the same struggles as entrepreneurs who are earlier in their career.

The right entrepreneur mindset is essential to your success.

Here’s how these entrepreneurs got their mind’s right, to grow their businesses.

On not feeling good enough

1. Joanna Weibe of Copy Hackers

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I’m most limited by my belief that I’m not good enough. It stays strong no matter what I accomplish. When I finish a talk at a conference, I beat myself up for days or weeks afterward – so badly that I usually have to take a sleeping pill for the week following the event. Crazy, right? I’m so certain of the inevitability of my failures – large and microscopic – that I don’t even like to schedule a newsletter to go out if I’m not sitting at my desk when it does… because what if a link is broken? What if there’s a typo? Ridiculousness. But, alas, that’s how I’m wired.

Overcoming it is a work in progress. But I really like what Mindy Khaling says: you can make mistakes, just don’t let them traumatize you. I tell myself that like a mantra. The more you put yourself out there and the more public you get, the more vulnerable you make yourself to the opinions of others. If I let that crap traumatize me, I’d never do or say anything again. So, for now, plenty of sleeping pills and Mindy Khaling books – haha!

Joanna Weibe is a conversion copywriter and founder of Copy Hackers, where she teaches startups how to write copy. She’s a frequent speaker at conferences, has been quoted in Entrepreneur, and Fortune, and has written for many popular sites. Since 2011, her eBooks have sold more than 50,000 copies.

Awesomeness from Joanna:

 2. John Lee Dumas of Entrepreneur on Fire

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Feeling like I “wasn’t ready”. I delayed launching EOFire for an entire month – I was supposed to launch in Aug 2012 and didn’t end up going live until Sept 22nd. I didn’t feel like “I was ready” to launch – what if no one listened? What if I launched and heard crickets?

Today, I call this my $100k mistake. Had I launched when I was supposed to in Aug 2012, then I would have made my first $100k 1 month sooner. Thankfully, my mentor Jaime Tardy came to me in Sept 2012 and said that if I didn’t launch the podcast, she was going to fire me 🙂

John Lee Dumas is the founder of Entrepreneur on Fire, an award winning 7-day a week podcast, where John interviews inspiring entrepreneurs. Through sponsorships, his flagship training program Podcaster’s Paradise, and other offerings, John has quickly built an empire that averages more than $250K in revenue each month.

Awesomeness from John:

3.  Sarah Peterson of Unsettle

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My biggest barrier was my self-imposed limits. For example, I thought I could never write 10,000 words in one day. I found it far too difficult to even write 2,000! But I challenged that belief about myself – that I couldn’t do it and that writing is hard for me – and broke through it. Another limit that I set for myself was about learning curves. I thought I could never learn how to do certain things that it turns out I absolutely can and have learned, just because I removed that self-imposed limit 🙂

Sarah Peterson is the founder of Unsettle, where she helps entrepreneurs stop settling for “okay” lives and careers, and start acting on their ideas.  She does this by providing motivation, inspiration, and direction to get started and keep the momentum going.  Her work has been featured on Inc, Boost Blog Traffic, and Elite Daily.

Awesomeness from Sarah:

4. Henneke of Enchanting Marketing

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The biggest barrier that has limited my business success has been my lack of confidence. I still find it weird that people want to pay so they can learn from me how to write better. How did I get here?

Coping with self-doubt has been quite a journey. I’ve learned to worry less about things I can’t control and to focus on my strengths and the things I enjoy doing. I also try to focus on my own journey rather than compare myself with others. I’ve learned to accept that my inner critic is part of me, and that she’s only telling me that I’m learning and doing exciting new things. And, for every new project, I try to get as much feedback as possible so I can be more confident I’m on the right track. I, for instance, try out ideas on my blog, I had beta readers for my books, and I’ve asked people to test-drive my courses.

I don’t think there are easy fixes to move beyond our self-limiting beliefs. You need to try different tactics and techniques to keep pushing your boundaries. Get out of your comfort zone, step by step.

Henneke is an irreverent copywriter, marketer, and business writing coach at Enchanting Marketing.  She helps her clients and students add sparkle to boring business blogs.  Henneke has authored two highly rated books on writing and blogging.  Her work has also been featured on many popular blogs, including Copyblogger, KISSMetrics, and Shopify.

Awesomeness from Henneke:

On stepping outside your comfort zone

5. Jon Morrow of Boost Blog Traffic

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I was really reluctant to charge high prices for training.  The most I could bring myself to charge was $597 for a home study course with hours upon hours of videos, plus group coaching calls every two weeks forever. It was already the highest priced product in my industry, and so I felt justified not going any higher.

But one day my mentor Frank Kern pulled me aside and said, “You know dude, you’re maybe the most successful blogger alive. You could easily sell a high-end training for $10,000.”

“What?!” I croaked. “$10,000? I don’t think I could ever go higher than $2000.”

He sat there silently for a moment and then said, “If you never go higher than that, you’re a coward.”

At first, I was really offended. He was calling ME a coward? Just to prove him wrong, I put together a $10,000 training and did a webinar to promote it, fully expecting it to fail.

But boy did I get the surprise of my life. On one webinar, I sold nine seats for $10,000 each, totaling $90,000. It was the most money I’d ever made in my life, all in just a few hours.

Was I uncomfortable selling it? Yeah.

But that’s when I learned you have to be willing to make yourself uncomfortable sometimes. You have to do it, even though you’re sure it’s going to fail, and sometimes you’ll be delightfully surprised.

Jon Morrow is the founder of Boost Blog Traffic, where he teaches his students how to build a popular blog.  Through the blog, courses, a membership site, and other other offerings, Jon has built a multi-million dollar business.  Prior to Boost Blog Traffic, Jon  was the former associate editor at Copyblogger, and editor at KissMetrics.

Awesomeness from Jon:

6. Tor Refsland of Time Management Chef

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When I was leaving my six-figure corporate job in order to follow my passion – to help online entrepreneurs SAVE TIME and ACHIEVE GOALS, I was uncomfortable…

Nah, who am I kidding?

I was SCARED sh*tless.


Because I had NEVER blogged before, and English was my third language.

So just considering to start a blog for the first time in your third language is kind of CRAZY banana, right?

So how did I overcome my fear?

People are either motivated by the pursuit of pleasure or the avoidance of pain.

In my case, I had both.

I was DEAD TIRED to work as a SAP system administrator for one of the biggest companies in Norway, where I was about to turn into a corporate zombie.

In addition, I had a strong BURNING PASSION to help online entrepreneurs to free up more time and reach their goals.

I was changing the perspective of my situation. I was telling myself that I was at a crossroad in my life.

If I were to stay any longer in my current job, I would most likely have more responsibility and a higher salary in a few years. This again would make it even HARDER for me to quit in the future.

I realized that it was NOW…

…or NEVER.

So I made it a challenge to myself. I told myself that if I could manage to succeed in this crazy journey, I would be able to do ANYTHING.

I had to put my productivity and achieving goals abilities to the test.

My strategy was to learn from the best bloggers in the world and APPLY their tips with some MASSIVE ACTION…

NOT for a day…

NOT for a week…

NOT for month…

but CONSISTENTLY – every single day.

For how long?

For as long as it takes.

The results?

Long story short, In about 10 months, I have managed to do the following:

  • I won the “Most Epic” blog post category on Jon Morrow`s blog – BoostBlogTraffic
  • I was included on the list of the top 100 personal development blogs
  • I got interviewed 9 times
  • My articles have been published on 24 blogs, including Tiny Buddha, Lifehacker, Pick The Brain, Addicted 2 Success and Jeff Bullas
  • Mentioned as an expert on 38 blogs, including SEM Rush, Ahrefs, Post Planner and Monster
  • I wrote a blog post that got 20 000+ page views in 6 days, 1400+ social shares and 76 comments
  • I challenged myself to get 1000 subscribers in 60 days. I only worked for 40 days and got 779 subscribers organically

As a blogger and online entrepreneur your success is depending on HOW you spend your TIME and how good you are at ACHIEVING your GOALS.

Am I about to slow down my pace?

Not at all.

I have just started.

Tor Refsland helps entrepreneurs stay out of the procrastination trap at Time Management Chef.  Tor practices what he preaches, by showing others how to work smarter, not harder.  His work has been featured on Addicted 2 Success, Pick the Brain, and Tiny Buddha.

Awesomeness from Tor:

7. Melissa Dinwiddie of Living a Creative Life

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My biggest mindset barrier—what I call a “self-installed glass ceiling”—was the story I told myself that I lacked the “money-making” gene. Without realizing it, I had bought into a false notion that some people are just born to make money, while the rest of us have no hope.

When I set out to make a real living from my art, rather than just a hobby income, this self-installed glass ceiling led me to aim way too low. My goal was to “just earn enough to get by,” which was all that seemed possible. And guess what? I made just barely enough to get by.

Years passed before I finally realized that—doh!—of course there is no “money-making” gene! Business and marketing are not innate talents, they are learned skills, which I could learn too, even if they didn’t come naturally to me.

The funny thing is that even though intellectually I know that the ability to make money is a learned skill, I feel like this particular glass ceiling has an infinite number of layers. I shatter one, only to find another one waiting behind it. So I just keep pulling out my metaphorical hammer. 😉

Melissa Dinwiddie, is an artist, performer, happiness catalyst, and creative instigator at Living a Creative Life.  Through her podcast, courses, retreats, and other offerings, Melissa helps others live a life in full-color.  Her work has been featured in The Huffington Post, Tiny Buddha, and Lifehack.

Awesomeness from Melissa:

8. Sonia Simone of Rainmaker Digital (formerly Copyblogger Media)

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It took me a long, long time before I was even willing to consider that I could own and run a business. I didn’t think of myself as a having that “entrepreneurial gene,” and I didn’t realize that it was something I could learn.

I’d look at other people who had built successful companies and think that they had something innate that I wasn’t able to access. And actually selling a product or service seemed about as attainable as going to Mars.

There were two things in my life that let me see the cracks in that mindset, and I really needed both of them.

First, I was reading blogs that helped me see that these were skills that could be learned, not talents that I needed to be born with. Copyblogger really was one of the first that showed me, step by step, how I could start to acquire these skills — I was a reader and a fan long before I was part of the team.

The other factor was urgency — my day job was conducting round after round of layoffs, and I was the breadwinner in my family, with a 3-year-old at home. I had to make it work, so I was willing to go through the hard work of looking at my own issues and putting a viable plan together.

When I went solo, I didn’t just have a plan B — I had a plan C, D, E, F, G, H, I, and J. I think I got to around E before I found the one that worked.

I don’t find that mindset is something you “fix” once — I still work on my mindset every day. As an entrepreneur, you have to keep improving your strengths, as well as keeping a watchful eye on your weaknesses and making sure you have them covered with the right resources.

Before I ran a business, I thought that launching a successful company would solve all of my problems. Now I know that it’s just creating a new set of problems — but they’re interesting, and even fun to solve. Each new phase of the business has its own challenges and issues. I wouldn’t trade it!

Sonia Simone is co-founder and Chief Content Officer at Rainmaker Digital, a multi-million dollar company that provides tools and training for content marketers and digital entrepreneurs.  Her teachings have helped thousands of entrepreneurs grow their businesses.  She’s written extensively for Copyblogger, speaks at industry conferences, and also has a popular podcast.

Awesomeness from Sonia:

On finding what works for you

9. Leanne Regala of Make Creativity Pay

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Very interesting question. My first thought is that we always have some mental barrier that’s holding us back. No matter how long we’re in business, it’s always going to be something.

But for me, when I first started out the biggest thing I had to learn was to trust my own intuition. My music studio was my third business but the first one I had major investment in – I was learning and I didn’t always feel confident in my decisions. I had a couple of people who I trusted to ask for advice, but I let others influence me or talk me out of decisions that I had already made. I made some huge and costly mistakes.

Once I started trusting my own inner voice, I started making better decisions and everything turned around for me. I got the experience that now helps me to help other creatives.

Leanna Regala is the founder of Make Creativity pay, where she helps creatives make good money from the work they love.  She does this through her blog, podcast, and 1:1 coaching and training.  Her work has been featured on Copyblogger, Boost Blog Traffic, and Lifehacker.

Awesomeness from Leanne:

10. Navid Moazzez of Virtual Summit Mastery

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The biggest barrier in mindset that limited my success as an entrepreneur was that I focused on too many things at once, specifically things I thought I had to do in order to start and grow a profitable online business, like blogging, podcasting and other things people told me to do etc.

All those things are great, but I didn’t grow my email list rapidly and I wasn’t generating a lot of cashflow in my business either. It wasn’t until I decided to focus on just ONE THING, I overcame this, and things finally started to take off for me.

The one thing I focused on was to create a successful virtual summit in my niche, and make it work for me no matter what. I’m glad I put in all the hard work to master this, because my entire business and life transformed after putting together my first summit.

So I highly encourage you to focus and go all in on the one thing that will have the most impact for you in your business right now. I always get much better results when I do that, and just recently I launched my Virtual Summit Mastery program, and one of the main reasons my first product launch was very successful and generated over $60,000 in sales from relatively small, but targeted email list of 1,500 people, was that I focused on only this launch for quite some time, and nothing else pretty much.

Navid Moazzez is the founder of Virtual Summit Mastery, where he teaches his students how to create a successful virtual summit to build their brand and grow their businesses.  Through his experience, consulting, and trainings, he’s quickly made a name for himself as the go-to person in this field. Navid has been featured on sites like Inc, Business Insider, and Entrepreneur.

Awesomeness from Navid:

11. Anthony Tran of Marketing Access Pass

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When I first started off as an entrepreneur the biggest barrier that limited my success was I thought that I had to do “What everyone else was doing.”  I use to read a lot of blogs, and listen to podcasts where everyone was always talking about the next “Big-thing.”  They would explain that if you don’t do this, then you won’t succeed.

This caused me to feel overwhelmed and I ended up having “Shiny-object Syndrome.”  I realized that what worked for someone else isn’t the exact recipe that would work for me, because I’m simply not like them.

Everybody is different and everybody has different skill-sets.  Some people are naturally good at writing, others may be a natural at speaking, while I’m naturally good at design.

When I embraced my natural talents and stopped resisting it, I found my niche and found what people were eagerly wanting to pay me for.  I went through a simple process where I took a piece of paper and folded it into three columns.  At the top of the column I wrote… Passion, Skills, and Compliments.  On the 1st column I wrote down a list of things that I’m passionate about no matter how silly it may have sounded (even my love for the game “Clash of Clans”).

Second, I wrote down all of my natural skill sets in the second column which included: public speaking, drawing, design, planning, etc.

Lastly, I wrote down in the third column a list of things that people compliment me on or offer to pay me to help them with.

I analyzed my lists and tried to find a common trend between the three columns.  What I came up with is that I’m passionate about creative art, and I’m naturally good at drawing and designing.

Lastly, people have given me compliments on my website designs, and people have offered me good money to help them with their own projects.  BINGO!!!

I’ve found my unique value proposition, and it’s not something that I have to fight hard to work at because I’m naturally gifted in this area and people are willing to pay for my services.

Embrace your natural talents and don’t let all the noise distract you from your one true calling.

Anthony is the founder of Marketing Access Pass, an all-in-one marketing training and services company.  Through website development, video trainings, and his podcast, Anthony gives his clients the information they need to succeed online.  Anthony has been featured on The Huffington Post, Entrepreneur, and several podcasts.

Awesomeness from Anthony:

On getting the most out of your work

12. Pamela Wilson of Big Brand System & Rainmaker Digital

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What held me back? Thinking small.

In the very early days of my design and marketing agency, I had a vision for what I wanted to achieve. That included making “just enough” to pay my bills, and maybe squirrel a little extra away in my savings account.

That perspective meant that when I created estimates for new projects, it was with an eye toward achieving my financial goals. But my financial goals were way too low!

A couple of things helped me get over this limited thinking.

In the earliest days of my business, I attended a one-day workshop tailored toward helping designers boost their business profits. It talked about techniques for networking, estimating jobs, systematizing tasks, and more. It was a great kick in the pants that showed me how to present myself as a professional who deserved the higher prices she was going to charge.

Later on, I joined a mastermind group: a group of business peers who serve as an informal board of directors for each others’ businesses.

This gave me a group of smart, savvy business owners to look up to. And we continuously pushed each other to eliminate clients and customers who didn’t appreciate us, and to aim for those who did.

Approaching your business with the right mindset is an ongoing challenge.

There’s no magic switch you can flip that will take care of this once and for all: you have to continuously take time to think about what you’re aiming for, and how you’ll get there.

Pamela is the founder of Big Brand System, and is now the Executive Vice President of Educational Content at Rainmaker Digital.  As an award-winning graphic designer and marketing consultant, Pamela has been helping entrepreneurs build brands and grow their business for years.  Her work has been featured on Copyblogger, Constant Contact, and UpMarket Magazine.

Awesomeness from Pamela:

13. Darren Dematas of Selfstartr

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For me, the biggest barrier is always thinking that I have to do it all myself. This is twofold.

A lot of times, I feel like I have to do all the ticky tack tasks myself. I’ve always had problems delegating because I have really high expectations and I often meddle in the task. When you’re an entrepreneur the buck starts and stops with you. So there is a lot you have to carry on you’re shoulders.

The second part is being an entrepreneur can get lonely fast. It requires a “roll up the sleeves” attitude and a lot of focus. Sometimes that focus can lead to isolation.

I’m doing my best to overcome this barrier by connecting with other entrepreneurs through social media. Im pretty active in FB and Skype groups. The support from others in the same boat as you can give you the extra push when you need it.

Darren is the co-founder of Selfstartr, where he teaches entrepreneurs how to build an eCommerce business.  Through blogs, podcasts, and other trainings, Darren provides demystifies the process of growing an eCommerce business.  Darren’s work has been featured in Adweek, HubSpot, and SEMRush.

Awesomeness from Darren:

14. Jon Nastor of Hack the Entrepreneur

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The biggest shift I made was adopting a 24 hour reset and allowing my mindset to start fresh every day. When I face a failure or a win in my business, I take it in and truly let it sink in for 24 hours, then I move past it. Dwelling on yesterday’s successes or failures for more than 24 hours will never allow you to progress to where you want to be in your business.

Jon Nastor is the host of Hack the Entrepreneur, a podcast that reveals the fears, habits, and inner-battles of big name entrepreneurs and those on the path to success.  Jon is also the co-founder of VelocityPage, a WordPress plug-in that allows anyone to build beautiful landing pages in minutes.  Jon’s work has been featured on Copyblogger, and Entrepreneur.  His first book will be released in December of this year.

Awesomeness from Jon:

15. Andrew Warner of Shade of Info

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The biggest barrier in my mindset was focusing on doing things myself — and being determined to make it on my own.

I thought that’s what being an entrepreneur is all about.  Proving that you can be successful with no help.  I learned that was wrong and struggled with all of the mistakes I was making.

How I overcame it was understanding that doing things on my own, or trying to do everything myself, isn’t the answer.

For example, when I was creating ebooks, I would try to create images for the cover. And even though I would eventually get it, it would take me 2 – 3 hours to do, whereas it would take someone that’s an expert in creating eBook covers, 20 – 30 minutes.

Point is, I learned to do and focus on what I’m good at … And that’s creating content, and let those that specialize in everything else specialize. This type of thinking has helped me grow tremendously.

Andrew is the founder of Shade of Info, where he helps bloggers blog smarter and turn it into a successful business.  Andrew practices what he preaches, and then teaches his students how to do the same with in-depth posts and case studies.  Andrew’s work has been featured on Boost Blog Traffic, Successful Blogging, and Carol Amato.

Awesomeness from Andrew:

16. Rob Wilson of Rob Wilson TV

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One of the biggest barriers in mindset that I had to overcome is what I call the “Superman Syndrome.”

You know, we all grow up in an academic environment where a premium is placed on individual achievement. Sure, you get a cursory group project every now and then, but those are mostly so that you are socialized in such a way that you won’t seem like a complete weirdo when you enter the real world. Or because the instructor is lazy and only wants to grade 25% of the papers this semester.

Either way, 16 years of being graded on your individual output teaches you, even if unintentionally, that’s it’s all about you. The problem is, in the real world, it’s the exact opposite. You need other people if you’re going to be successful.

The idea of being “self made” is nonsensical. Every person we admire had help from someone, or most likely many people on their path to the top. But all of those people don’t appear on the cover of Forbes. Or Fortune. Or Black Enterprise. The stories of success are never about the Indians, they’re always about the chief, and that’s what drives our vision of what success looks like.

I grew up as an only child, and I’m sure that only exacerbated things for me.

So, I had to embrace the fact that I was going to need help if I wanted be come successful. There are very few, if any, truly one person businesses that are successful.  You can only be the CMO and the janitor for so long until you realize that such a situation is unsustainable and that your precious, limited time is much better spent on the areas where you add the most value. Leave the rest with others.

When I stopped trying to be Mr. Everything, simply because I wanted to be able to say to Oprah in my future interview that “I did this all by myself,” it’s amazing how much faster things started to take shape. More opportunities, more accolades and more income.

In short, I learned to focus on my true superpower instead of trying to be Superman.

Too bad we aren’t taught that in school.

Rob Wilson is a financial advisor, and the founder of Rob Wilson TV, where he teaches his students and clients how to become financially independent.  Rob has often been called “Hip Hop’s Financial Advisor” because of his work with professional athletes and entertainers.  His work has been featured in Black Enterprise and CNN.

Awesomeness from Rob:

It’s time for you to overcome your mental hurdles

The success of your business depends on it.

Follow the lead of these entrepreneurs, or explore different options on your own.  Find what works best for you.

Don’t let your barriers limit your success any longer.

A great first step in doing that is to acknowledge your own mental struggle that’s plaguing you most at the moment.  Drop it in the comments below.  The public declaration will lessen the power it has over you.

And if you need help with a next step to help you kick your hurdle to the curb, I’ll give you a suggestion to help you along.

You can be free from the limitations that have held you and your business back.

Are you ready to set yourself free?