It took me over 7 years of working as an employee before I decided it was time to start a business.

For years, these questions held me back:

  • How will I pay my bills if I fail?
  • How humiliating will it be to tell my friends and family that I failed?
  • Do I have what it takes to succeed on my own?

I guess you could say I had a major fear of failure.

But what made me finally take the leap was looking at the potential upside of entrepreneurship. I didn’t realize that there was so much more to becoming an entrepreneur besides it being a way to make more money or to be your own boss.

And you know how I found out what the upsides were?

By listening to and reading about other entrepreneurs my age that were killing it…all because they decided to take a risk on themselves.

That’s what entrepreneurship is all about: being willing to take a risk on yourself.

If you’re thinking about starting a business and you’re scared, it’s ok. It’s normal.

But the definition of courage isn’t about not being fearful, it’s about overcoming your fears.

I don’t want you to wait 7 years like I did. You can start today.

And it starts with inspiration.

I want to inspire you today with the stories of 16 of the youngest, most successful entrepreneurs I could find. I asked each of them this simple question: What Held You Back From Taking The Leap Into Entrepreneurship?

Their answers are below. If you enjoy this article, please share it. Use it to motivate as many aspiring entrepreneurs as you can, to take a risk on themselves.

Click To Tweet: What’s holding you back from becoming an entrepreneur? Here are 16 reasons why you should take the leap:

John Lee Dumas - GenY Success

John Lee Dumas

Entrepreneur On Fire

“In one word…significance. I was tired of a life of meaningless transactions. I wanted to contribute significance to the world, and EntrepreneurOnFire has allowed me to do just that.”

  • John’s podcast, the Entrepreneur On Fire Podcast, is one of the top rated business podcasts on iTunes. It was awarded best podcast of iTunes in 2013. He’s featured Tim Ferriss, Seth Godin, Pat Flynn and several others.
  • He’s grown his business to 7-figures in just a little over a year and currently brings in over six-figures in profit per month. Check out his income reports.
  • He’s been featured in Forbes.
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Jordan Harbinger - GenY Success

Jordan Harbinger

The Art of Charm

“My business was taking off and the legal market tanked. Instead of finding another job I hated I decided to go all-in and run The Art of Charm full-time which was the best thing I’ve ever done.”

  • Jordan’s podcast, The Art of Charm Podcast, is one of the top-rated business podcasts in iTunes along with one of the top 100 podcasts in iTunes overall.
  • Jordan’s company, The Art of Charm, has coached hundreds of men over the years. The Art of Charm bootcamps are where “where ordinary guys become extraordinary men.”
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  • Jordan has been kidnapped, twice. And he’s lived to tell about it. Listen to his story here.
  • Make sure to check out the episode with Seth Godin, where Jordan digs in about the importance of failure in entrepreneurship.
  • Check out the episode with Judy Robinett, who talks about how she networks with billionaires (yep that’s with a “b’).
  • And my personal favorite, the episode with Adam Grant, where they talk about how giving is the best way to get ahead.

Sophia Bera - GenY Success

Sophia Bera

GenY Planning

“When I was considering starting my own financial planning firm I went out to dinner with my mentor and he asked me this very important question: ‘What’s the worst thing that could happen?’ I immediately started coming up with excuses and he stopped me and said, ‘No, Sophia, the worst thing that can happen is that you’d have to get a job in financial planning!’ Once I realized that the worst that could happen was that I’d have to get a job, I knew I had to launch my firm and become an entrepreneur. When plan B isn’t so bad, you should go for plan A. There’s often less risk than we think. Now that I’m an entrepreneur, I feel like traditional employment is really risky because you could get fired at any time and lose 100% of your income.”

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Sean Aiken - GenY Success

Sean Aiken

One Week Job

“We often associate great risk with taking the leap into entrepreneurship. Well, I ask you, what is the greater risk? Avoiding some discomfort in being vulnerable, the possibility of it not working out, the possibility of failing and learning from it, or, to be at the end of your life with regret? Sadly there is such a thing as ‘too late.'”

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Matt Wilson - GenY Success

Matt Wilson

Under30Experiences & Under30CEO

“At 19 years old a guy from Saskatchewan, Canada told me he had found the meaning of life. ‘Some people collect money, cars, power… but entrepreneurship isn’t about that. To me, life is about collecting stories and experiences, and entrepreneurship is that vehicle for my collection of stories.’ When these stories become about serving others through the vehicle of entrepreneurship, then you are truly living the dream.”

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Brandon Epstein - GenY SuccessBrandon Epstein

Entrepreneur Fitness

“Becoming an entrepreneur was a move of necessity for me. I had the 9-5 whatever jobs during the summer before graduating from college. Upon graduation, I couldn’t imagine plugging back into a job where I had to work on someone else’s dream and vision for 8-12 hours a day. Instead, I applied for research positions to explore the field of neuroscience and sport psychology. When I didn’t get any of those positions, I decided that I would forgo the extended formal education and just start an app company. Through apps, I could share the knowledge I had in the field of sport psychology with thousands of people without needing to get another money and time expensive degree. That was the start of the journey and I haven’t looked back since.”

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Amanda Abella - GenY SuccessAmanda Abella

“I was inspired to journey into entrepreneurship because, between the Great Recession and working as a recruiter, I knew first hand that the only way to make the money I wanted on my terms was to work for myself. What finally pushed me to make the leap and quit my job was when I realized that a regular job is actually less secure than entrepreneurship. You could get a pink slip next week and all your income would be gone. With entrepreneurship there are always ways to replace income or make more money.”

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Ryan Jenkins

The Next Generation Catalyst

“I truly believe we rob the world when we decide to play small and neglect to share our unique talent and expertise. We all have a unique skill or perspective that can add value to others, and it’s selfish to think otherwise. It’s not about you but rather the people searching for your knowledge or passion. You may not change the world but you can change someone’s world. That was enough for me to take the leap.”

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Michelle Ward - GenY SuccessMichelle Ward

When I Grow Up Coach

“What inspired me the most to become an entrepreneur? My own damn realization that being an entrepreneur fit into what I saw for my future self, and that becoming a career coach for creatives is something I was uber passionate about. When I gave up on my lifelong dream of being a musical theater performer, it was just plain unacceptable for me to spend the next 35+ years of my working life in something that didn’t light me up. I knew I had to create it for myself, and The When I Grow Up Coach was born!”

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Danny Rubin - GenY Success

Danny Rubin

News To Live By

“You know that Gandhi quote ‘Be the change that you wish to see in the world’? Well, I took it seriously. As a TV reporter, I had grown tired of newscasts full of gloom and doom. I decided to create a website that shows young people how top stories can make us better. I felt like I needed to take on the project because, if I didn’t, then who would? For so many reasons, News To Live By continues to be the smartest professional decision I ever made.”

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Josh Bauerle - GenY Success

Josh Bauerle

CPA On Fire

“I finally became completely fed up with spending 40 plus hours a week working to make someone else rich. I was tired of living life just trying to get to Friday and then spending every Sunday dreading starting a new week. I hated living paycheck to paycheck and having my pay completely dependent on what someone else felt I was worth or could get away with paying me. When I realized that starting my own business had the potential – though not a guarantee- to solve all of this, it became a no brainer decision.”

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Gabrielle Jackson - GenY Success

Gabrielle Jackson

Millennial Solution

“People often confuse owning a business or working for yourself as being an entrepreneur. It can be, but really an entrepreneur is a disuptor of processes and challenger of the status quo. I never saw myself as an entrepreneur until I realized I could use my skills and passion to be a part of the engine of positive change. Now I have a way to make a living and a difference.”

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Hannah Becker - GenY SuccessHannah Becker

The Motivated Millennial

“Like many industries post-recession, my original career choice had very limited job offerings; the majority of which required 60+ hour work weeks and disparagingly low salaries. I knew I could create a business that generated comparable rewards; was greatly surprised when it turned into 30 hour weeks with greater financial offerings than my original career choice. I was finally able to provide my family with the resources—time and money—that I’d hoped to achieve.”

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Arman Assadi - GenY Success

Arman Assadi

Why I Left Google

“A burning desire for freedom. The freedom to do what I want, when I want, how I want — along with the opportunity to actually live to my full potential. I’ve always been a non-conformist. I never fit into the corporate world, and didn’t really enjoy the educational system either (other than the occasional professor/teacher that encouraged my style). Where I thrive is self-directed learning, collaborating with others, and educating. Solopreneurship was the solution to that.”

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Lindsay Smith - GenY Success

Lindsay Smith

Lindsay Smith Coaching

“I was inspired to get into entrepreneurship for myself because I wanted an adventure! There is no limit to what you can do. I also believe starting your own business will grow your character and show you how much true grit you’ve got. I took the risk because I had to know if I could do it. I was inspired by those around me who took the risk, worked hard and smart, and made something new to bring to the world.”

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Ryan Avery - GenY Success

Ryan Avery


“Us becoming entrepreneurs came down to two things. When our kids ask us ‘did we go for our dreams’ we want to be able to look at them and say ‘yes.’ And why be good when you have the potential to be great?! It’s worth the try to go after your dreams because your dreams can help other people.”

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Inspired? Need more?

Get inspired with my free ebook containing the 50+ resources young entrepreneurs use everyday to help them be so successful.