overcome fear of failure

How to Overcome the Fear of Failure

By Bryan Orr

For the last few months my 15-year-old son, Alex, has been talking about going to the tree nursery next door to our house and asking the owner for a part-time job. And talking about it… and talking about it. I brought it up to him a few times, just casually asking if he had gone to speak with them; knowing that he hadn’t.

I know how he feels, because it was the way I felt before my first job interview, and the first day on the job, and the first customers home I walked up to by myself, and basically how I still feel every time I need to pick up the phone and ask for something.

This certainly isn’t a universal emotion, we all know someone who has no problem talking with a total stranger, asking themselves over for dinner or making their desires known with zero reservations.

But if you are like me….

Asking for something, putting myself out there, making my desires known is a huge emotional risk and it comes with a fear deeper than my fear of spiders or sharks, almost (but not quite) as scary as parking garages.

The fear of rejection and failure.

Every good thing that has happened in business for me has come at the tail end of overcoming the fear of failure.  Here are my tips for overcoming this internal resistance.

Move Quick

Many times fear is the result of over thinking, and over thinking is the result of moving too slow. I’m not saying be haphazard, but  don’t allow yourself space for reflection within the work day, you can have time to worry about all the crazy things you did when the day is over.

Make HUGE Goals

I’ve heard these called BHAG’s or “Big Hairy Audacious Goals” and they help you overcome resistance by taking your focus off of YOU-When your eyes are set on something so huge and looming that your fears become small and insignificant in comparison. Don’t plan to get 10 new sales next week, commit to getting 150!

Give Everyone Permission to Heckle You

Step #1 in giving others permission to heckle you is to stop being sensitive about your fears and failures. If you might get offended if one of your team members told you to “stop making excuses and pick up the phone” or “get off Facebook and get to work” then you aren’t in a good spot. The people around you who truly want you to win are the ones you want to give permission to call you on your fears and kick you in the gluteus maximus when you need it.

This Saturday I watched Alex put his shoes on and walk over to the fence by the nursery and watch the workers, only to walk back in a little bit later. I gave him a quick heckle and let it go.

Yesterday my wife posted on Facebook while I was at work: Alex had worked 6 hrs at the tree nursery and was told he could work more any time he wanted.

He did it.

Just the start of a life overcoming the fear of failure, and two proud parents.

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Bryan Orr
Bryan Orr is a blue collar business owner who helps executives and business owners use storytelling to communicate powerfully with customers and staff. Bryan is a founder of an award-winning small business in Orlando, Fl as well as sought after podcast producer and consultant. Get to know him at Bryanorr.com.


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  1. I’m glad I’m not the only one who feels this way. Especially when the sales world seems like it was made for and by extroverts. Sales calls are like pulling teeth but I think once you’ve let yourself drown in that pool a little you get used to it and it’s not so painful.

  2. I totally agree that fear can grow from overthinking. But I think that fear is somewhat healthy if it’s moderate. I believe in embracing the fear and overcoming it slowly, which is the same as the “Big Hairy Audacious Goals” you mentioned
    I had the same experience on my first few interviews. In the past, I had purposely missed a bus or train to miss an interview. But then the fear of failure in life became so much bigger than the fear of doing an interview. That pushed me to not skip interviews anymore.

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