How Top Entrepreneurs Overcome the Dreaded Fear of Failure

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Many people are afraid to take action, especially when it comes to real estate investing, for a variety of reasons. I know I was. Getting into real estate can seem risky and intimidating at first.

This is why many people start out with a duplex, so that if they do have a vacancy, only half of the unit is empty. Most investors quickly learn as they get more units that SFR (single family residential) tend to do much better, with the tenant covering more of the expenses. But it is these investors who took action to begin with.

Often, I think we’re afraid of what others will think if we fail at something. In reality, some of the most successful people have failed a lot, but they somehow learned from their mistakes and moved on.

Maybe it’s the way we’re brought up or the way we’re taught in school. Think about how we memorized things, received report cards, and were encouraged to work alone, as opposed to working as a team. For example, the school system considers it cheating if you compare answers with someone else. So, in a way, we’re taught to go at it alone and be judged on our performance.

Related: The 3 Most Important Questions Entrepreneurs Should Ask Themselves

When I first started out in real estate investing, I was scared to death. Yet I was determined, and I did have some skills, as I was handy and a hard worker. I used to think about what the worst that could happen was and that I’d have to be okay with that if I wanted to try to invest in real estate. My feeling was that if I did lose money, the worst case scenario was that I’d go broke, and that was a place that I was already very familiar with. I just had to find a way to ignore all of the naysayers in my life, and I did this by hanging out with other real estate investors.

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How Do You React to Failure?

Recently, I was at a conference in Austin, and a fellow note investor was telling me how he had bought 8 first liens, and it was a disaster, as he hadn’t really made any money. I asked him what he had learned from the experience. His biggest thing was that he didn’t really have enough experience or education, and he didn’t really know what he was doing. Obviously, that can be a problem.

I told him of my first experience in the nonperforming note business, when my partners and I bought four notes to start out with. We got wiped on two, but we hit a home run on one — and a grand slam on the other. I told him that if we had only bought the two disaster loans, we might not have even been talking to each other.

The best advice I could give him was to learn from any mistakes and move on. Maybe next time he can learn more about the business and possibly find a coach. If nothing else, hopefully he will be able to get to know his note seller next time he plans to purchase.

But how does one overcome the fear of failure?

Harness the Fear of Regret

The other day, I was reading an interview with Elon Musk on the Inc. blog, and in the article, Elon was asked if he had any fear, to which he replied that he felt fear very strongly. After all, he’s been working furiously on things like TESLA and SpaceX (a private space program). What has more potential of failing, right?

Related: Mind Over Matter: Are You Standing in the Way of Your Own Entrepreneurial Success?

Then, he said something that was pretty amazing to me, and it was describing a concept that he dubbed “The Call.” Essentially, any time that he had fearful thoughts of failure, he would harness that energy and turn it into a fear of regret, or in other words, a fear of looking back and knowing that he didn’t do everything he could. He said that aspiring entrepreneurs make The Call when the fear of not doing something overpowers their fear of actually doing it, and it forces them to take action.

So, I guess it’s more about how we react to failure than how we perceive it as a possibility. Yet it’s still best to be prepared. Network with others who have failed before, and of course, try not to repeat the same mistakes over and over again.

There may come a point with any aspiration or endeavor where you just have to ask yourself, “Would I rather live and die knowing that I tried and failed, or live and die with the regret of never even trying?”

Entrepreneurs: How do you overcome fear of failure and take action?

Leave your best tips below!

About Author

Dave Van Horn

Since 2007, Dave Van Horn has served as president and CEO of PPR The Note Co., a holding company that manages several funds that buy, sell, and hold residential mortgages nationwide. Dave’s expertise is derived from over 30 years of residential and commercial real estate experience as a licensed Realtor, a real estate investor, and a fundraiser. As the latter, Dave has raised over $100 million in both notes and commercial real estate. In addition to his investments and role as CEO, Dave’s biggest passion is to teach others how to share, build, and preserve wealth. He authored Real Estate Note Investing, an introduction to the note investing business, helping investors enter the “other side” of the real estate business.


  1. Frank Romine

    Good read. I starting taking more risks and thinking out side the box when I surrounded myself with the people I wanted to become. If you are not taking action there is a good chance the majority of the people in your circle aren’t either. Start rolling around with risk takers.


  2. Michael Woodward

    Great question Dave! I’m “all-in” with my business and all of my chips are in play all the time. Fortunately things are going well with it but that still doesn’t stop the worst case “what-if” thoughts from entering my mind (especially in the middle of the night). I think for most people, those thoughts won’t go away completely until they’ve got enough reserves that it no longer matters. It’s easy to lose (or even give away) your profits when you’ve got plenty but it’s agonizing to lose when you need it.

    In my opinion, fear that paralyzes the unprepared person is a good thing……….call it a safety valve. Fear that paralyzes someone that’s done all the necessary due-diligence, created a solid plan, and knows how to execute the plan is probably rare. Preparation and strong execution should overcome almost all fear but I think general “fear” is likely inside every entrepreneur.

    • Dave Van Horn

      Hi Michael,
      Thanks for sharing your insight. I agree that sometimes it’s about burning the boats. This makes me think about my youngest son, who moved to LA to pursue filmmaking. When questioned about whether he had a plan B, he would say “my plan A is my plan B.”

  3. chuck w.

    Fear is the number #1 problem with just about everything. It has kept many a good man tied down to a job and life that is totally unsatisfactory. The fear thoughts attack me in the early morning. I wake up to my mind trying to offer me lots of “what if’s”. So I have a little paragraph I have started reading every morning.
    “Do not allow your thoughts to become greater than you. No matter what your thoughts tell you, don’t listen. Remember your thoughts are not your friend. Your thoughts try to confound you, confuse you. And they will tell you all kinds of things. Do not listen to your thoughts, even your good thoughts. Transcend everything, go beyond your thoughts to your bliss, to your joy, and to your happiness.”
    Robert Adams

    • Dave Van Horn

      Hi Chuck,
      Thanks for sharing that quote; I’m sure it’ll help a lot of people.
      Sometimes when I wake up in the morning with fearful thoughts of something not working out, I’ve found that exercise helps me feel more positive.
      All the best,

  4. Colin Smith

    I’m working towards quitting my 9-5 in the next few months and there is definitely quite a bit a fear of losing that stable income.. I just have to remind myself of my potential outside of where I am at now.

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