5 Simple Ways to Overcome the Fear of Becoming an Entrepreneur


At the end of every EOFire podcast episode, John Lee Dumas asks his guests, “What was holding you back from being an entrepreneur?”

One of the most common answers is “fear”.

Fear of uncertainty, fear of failing, fear of the unknown, and fear of not knowing enough.

After hearing so many entrepreneurs, many of whom I greatly admired, say fear held them back, I started to think, “Was I afraid”?

I sold cassette tapes in elementary school, started a drop-ship business on eBay, and ran a decal business where I ranked number one on Google for highly relevant terms. I was a hustler! There was no way I was afraid, right?

After a few days of soul searching, I started to realize that it was actually fear that was holding me back. I disguised it as family, mortgage, kids, and wrong timing, but at the heart of it all was fear.

That fear would have held me back from now having the business of my dreams -- a six-figure business that provides the freedom to spend time with my family.

I don’t want fear to hold you back. Here are five simple tips that finally pushed me to take the entrepreneurial leap and continue to throttle me forward.

1. Be Grateful for Your Skills

For the past year and a half, I’ve been journaling using The Five Minute Journal. I start each day listing three things that I am grateful for. At first, I generally wrote down things that were external to me, such as my wife, kids, parents, siblings, podcast audience, network, etc.

However, recently I started writing things down that were internal to me. My hustle, persistence, thirst for knowledge, and my willingness to take action. Doing so allowed me to build more and more confidence in myself and made me realize how far I’ve come.

2. Join a Community

I was a serial sidepreneur, always building side businesses.

Side businesses are perfect. They give you the thrill of entrepreneurship without the real risk. However, I was just tricking myself into thinking I was a real entrepreneur.

Then I joined the EOFire Elite mastermind where I meant many other sidepreneurs who were taking the plunge into their business full-time. Many posted about setting a date to leave their corporate job and seeing their courage allowed me to finally set a date and take the leap myself.

3. Recognize the Fear

As I stated earlier, I didn’t think I was afraid at all. I am a go-getter. I’ve started many businesses on the side.

However, now three years into running my business full-time, let me tell you that having a side business is not the same thing. Having your back up against a wall is an experience that you can never have when you are doing things on the side.

I was replacing fear with other excuses such as having a family, a mortgage, and not knowing enough.

4. Hire a Coach

One of the first things I did when I was planning my leap was hire a business coach. She kept me accountable and helped me think through all my revenue streams.

The key to hiring a coach is finding someone that can help you with “just-in-time learning”. It is a term that I heard from online entrepreneur Pat Flynn, where you learn a key skillset just in time before you need it.

5. Interview Your Heroes and Build an Audience

One of the single best things I’ve done to take the entrepreneurial leap was to build an audience first. This single action has allowed me to build multiple revenue streams including selling online courses, running an agency, running live events, and publishing apps.

Having an audience also forces me to continue going when times are tough. I don’t want to let my audience down and quit on them.

While there are many ways to build an audience, I’ve found that interviewing my heroes was one of the easiest and fastest ways to gain instant credibility.

In 2013, when I first started my podcast, no one in the app space knew me. I started out interviewing successful people in the app space and leveraging their names to build an audience.

Then six months into the podcast, the audience began to come to me for app marketing advice. At the time, I didn’t know what to charge or how I was going to execute, but I took that one client on. Then more audience members started coming to me, which in turn gave me more confidence and the knowledge to continuing growing.

Now, I’ve been able to make a name for myself in the app space and it all started with interviewing my heroes on a podcast.