How to Overcome the Fear of Failure

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Sometimes it’s difficult to pinpoint a fear of failure. It often manifests as a gnawing feeling that holds you back, keeping you from taking that “next step” that will bring your business to a new level. It may be shrouded in an excuse:

  • I don’t know which avenue to pursue.
  • I don’t have enough resources/knowledge/connections.
  • This idea isn’t big enough or good enough to be a full-fledge business.

At the root of each of these excuses is fear. Fear of doing something that isn’t impressive enough, fear of losing your investment or fear of being an imposter. Most serious entrepreneurs aren’t afraid of sacrifice; we understand that sacrifice is necessary. But it is the fear of losing that sacrifice and the thought of what others will think of us that holds us back.

If you are struggling to bring your business to the next level, I challenge you to do a little soul-searching to discover the emotional element of your hesitation; I am betting that you will find the answer is fear.

So how did I learn to embrace fear as a growth tool? Here are some the game-changing strategies that made it possible.

Take Action

I hit a tipping point in my life. I realized that while the fear of failure would always be there, the fear of living my life with regrets was greater. I was successful in my professional life but I knew that I was destined for more; that I needed to replace my current frustrations with excitement if I was going to truly enjoy life.

The biggest risks come with the greatest rewards and those rewards are often presented in the experiences and memories that are fashioned along the way. We can all think back to a time (probably in our teenage years) when we took a big risk; we pursued a romantic interest or challenged an authority figure. Regardless of the outcome, those experiences shaped you as a person; they helped you grow.

The same is true in business. Understand and accept that you might fail. Understand and accept the worst case scenario. Then move on with that knowledge; use it as a catalyst that propels you to do your best work.

Early on, I was fortunate to receive very positive feedback from the Foundr community. With each issue, readers were reaching out to tell me the profound impact I was having on their lives; that was the gold that kept me going. Receiving this type of validation from the community you are serving allows you to overcome “imposter syndrome.” Eventually you realize that you are worthy of your dream.


This is one of the many emails I receive on a daily basis from Foundr community members.


Embrace Obstacles

An excellent book, written by Ryan Holiday and entitled The Obstacle is the Way really helped me overcome my fear of failure. In his book, Holiday writes about embracing each obstacle and each failure as an opportunity to improve your business. Instead of being afraid to fail, be excited to learn; this shift in thinking makes it so much easier to forge ahead in spite of the current struggle.

I was given a wonderful opportunity to learn in the form of a lawsuit. In the early stages of Foundr (I was calling it something else then) I was sued for trademark infringement by a big company. The name I was using at the time was covered by their trademark. I hadn’t done adequate research to uncover this fact and as a result I was faced with the possibility of losing everything I had worked so hard to achieve. Looking back, I am so incredibly thankful that this happened; even the timing was perfect. Not only did I learn a lot about trademark infringement but I ended up with an epic brand in the process.


This piece of branding was created when we were selected to featured by iTunes; which was such an incredible honor. 

Surround Yourself with Genius

A Jim Rohn quote that I love is: “You are the average of the five people you spend the most time with.” This is so undeniably true. My mentors have had such a profound impact on my mindset and my business that this qualifies as my biggest success hack.

Surrounding yourself with super successful, positive influences provides you with motivation, advice and perspective. It will help you understand that someone you know, a real face and personality, has overcome the same fears, struggles and doubts you are facing. These examples in your life keep you focused on the amazing possibilities and become massive contributors to overcoming your fear of failure.

Accept the Coffee Challenge

Feeling that your product isn’t worthy of payment or of adequate payment is huge obstacle that must be overcome in order to find success. I used a simple exercise introduced to me by Noah Kagan of AppSumo to get past this hurdle. In his aptly named “Coffee Challenge,” Kagan encourages you to ask for a discount at a coffee shop. The object is not to save money or to get something for nothing; instead, it is to get you out of your comfort zone in a conversation specifically about money.

Too often, money is treated as a taboo topic; we avoid talking about it because it seems uncomfortable. If we can get past this feeling of discomfort and embrace money for what it is (a simple transaction vehicle) we will gain a confidence that permeates all of our business dealings.

Be Present

Dwelling for too long on the “what-if” scenarios will leave you paralyzed with fear. Recognize that this can manifest itself as over planning or excessive analysis and result in “paralysis by analysis” by which you convince yourself that you need an ever-increasing amount of data before you can make a decision.

Data gathering is great; as is research into your market, products and community. However, do not allow the pursuit of data to hinder your business’ growth. Simply review the information, fabricate your best and worst case scenarios, take action and then absorb your current state.

It’s so easy to fall into the trap of being “too busy to think.” You move forward, attacking each task with vigor and it becomes so exhausting that you don’t have the time or energy to develop your business. Production versus business development is a constant balancing act. Both aspects must be healthy in order for your business to thrive.

A consistent shipping deadline has helped me maintain focus on this balance. We have resolved to ship our magazine in the middle of every month, without fail. I would never let my readers down. I also know that if I am going to continue to be successful I have to invest in the future of the business as well. The right balance is a moving target; during a product launch most resources are focused on the immediate tasks. However, there are times when I allow the tools and people I have put in place to provide for the daily tasks of the business so that I can focus on development.

Overcoming a fear of failure is a struggle that all entrepreneurs face. Recognition is the first step in overcoming; evaluate your unique situation and what it would take to change it. Then ask yourself why you haven’t done it yet. Fear will always be there, but don’t allow it to be the reason or the excuse for an unfulfilling

  • Greg Bardwell

    Good one. “Fear is the path to the dark side.” Very true. Working and tackling the fear head on is the path IMHO.

    • Nathan Chan

      Spot on Greg 🙂

    • Nathan Chan

      Agreed!! That’s a great one!

  • Quentin Green

    Just found this post, but love it. I also believe finding your true motivation or “Why” (as Richie Norton puts it) helps overcome barriers. I’ve written posts on overcoming fear (including all limiting beliefs) as well as building confidence, which I believe is also important. I’ve even quoted Noah too! Also check out his “high five” challenge.

    • Nathan Chan

      That is such a great point @disqus_TcbJQk7zPn:disqus, your WHY is so extremely important. Once you find that purpose you will care so much less of what others think.

  • Adam Franklin

    Hey Nathan, I’ve done the Noah Kagan coffee challenge twice now. It’s highly uncomfortable! And totally worth putting yourself through. For the record, one said No, and the other gave me a free coffee.

    • Nathan Chan

      How good is it @adamfranklin:disqus

  • Clint Carpenter

    Great article. Another tip to reduce fear of failure. FAIL. Everytime I move forward after a failure I fear the next one less.

    • Nathan Chan

      Thanks @disqus_1cpVRXpIqy:disqus – Glad you enjoyed it!


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