What’s Holding You Back From Taking The Leap Into Entrepreneurship?

Estimated read time 8 min read

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.

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.
Make Sure To Check Out
  • John spent several years in the Army and didn’t grow up wanting to be an entrepreneur. His story is very inspiring for people getting into the entrepreneurial game a little late.
  • Make sure to check out his podcast episodes with Seth Godin, Gary Vaynerchuk, Tim Ferriss, Pat Flynn, Jaime Tardy, Ramit Sethi, Ryan Holiday, Sally Hogshead and Hal Elrod.
  • John wrote Podcast Launch, a book that includes written and video tutorials on podcasting, and it’s only $.99.

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.”

Make Sure To Check Out

  • 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 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.”


  • Sophia was rated one of the “Top Financial Advisors For Millennials” by Money Under 30.
  • Sophia has been featured in the Huffington Post, AOL’s Daily Finance, Business Insider, Forbes, Inc. and the list goes on! (full list here)
  • Sophia bought her first house at 21, unheard of for most people that age.

Make Sure To Check Out

  • Sophia was on the Entrepreneur On Fire podcast to talk about her story.
  • Sophia talks about what she learned from her experience as a homeowner at the age of 21 on Yahoo.
  • Sophia’s list of 17 financial terms every millennial should understand.

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.’”


  • Sean had 52 jobs in 52 weeks…holy cow! Check out his epic journey for a better understanding of WHY he did this 1-year project.
  • Sean has been featured in the NY Times, Time Magazine, Huffington Post, CNN and Good Morning America.

Make Sure To Check Out

  • In Sean’s TedxVancouver talk, he talks about what makes you come alive.
  • Check out the documentary of his journey.

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.”


  • Matt has been featured in Entrepreneur, Killer Startups and has contributed to Business Insider.
  • Matt’s company, Under30Experiences, takes young, energetic people on travel experiences across the world.

Make Sure To Check Out

  • Matt’s interview on The Art of Charm Podcast, where he talks about travel and why it equals success in life.
  • Matt’s interview on the Entrepreneur on Fire Podcast, where he talks about an AHA! moment he had on an iceberg in Iceland.
  • Matt’s interview on the Eventual Millionaire, where he talks about balance and building a startup the right way.

Brandon 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.”


  • Brandon has been featured in The Utopian Life, The Remarkably Human Podcast and The Entrepreneur’s Library Podcast.

Make Sure To Check Out

  • Brandon is offering a free 30-minute coaching session to entrepreneurs looking to achieve peak business performance.
  • Brandon’s podcast, The Entrepreneur Fitness Podcast, has a great selection of guests that he talks to about entrepreneurship, fitness, nutrition and performance.

Amanda 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.”


  • Amanda contributes to the Huffington Post and has been featured in Forbes, Business Insider and many more!

Make Sure To Check Out

  • Amanda was featured on the Entrepreneur On Fire Podcast to talk about her journey.
  • Amanda’s book, Make Money Your Honey is about how to make money more effectively as an entrepreneur.

You May Also Like

More From Author