Overcoming Your Fear of Failure

Over the weekend, my wife Lindsey and I along with my brothers and their amazing wives were in Dallas. At a restaurant we played a game that would pose a question to our group then want us to discuss and answer it for the group.

One of the questions that I answered without question but stuck with me was this one:

Would you prefer to try and fail or never try?

I realize this is very unscientific of course. But the game said 81% of people playing answered “Never try” versus 19% who answered “Try and fail.”

That hit me hard. Upon reflection and mere gut intuition alone, I can see how that stat might be accurate for the majority of people.

But I’m a try and fail kind of guy. I’d rather fail fabulously than live with the regret of never knowing what could have been.

So this got me thinking about our fear of failure (been there, done that). And I want to offer some compelling reasons why you should try … and practical helps for doing so. To help you get over your paralyzing fears and to attempt great things with your life.

First Things First: Some Disclaimers

  • This post is about getting over the fear of failure and trying, starting, taking action on your dreams
  • Those hopes, dreams and goals should be positive, ones that don’t cause destruction or harm to other human beings
  • Quitting is different than trying. It doesn’t mean you shouldn’t quit. I’m a quitter. But that’s all for another post. See Seth Godin’s The Dip for a great primer on when to quit and when to press on.

So with that, let me first give you some reasons for why never trying is a bad decision and add some personal perspective on them.

Why Never Trying Robs and Costs You More Than Failure:

  • You rob yourself of priceless experiences — Life is all about experiences. When you choose not to experience something you’re robbing yourself. In fact, the happiness experts actually suggest you BUY experiences.
  • You don’t learn anything new about yourself or the world — Failure is learning. Learning is failure. As my infant son learns to crawl and walk, I see continuous failure … and continuous learning. If he didn’t fall down, he wouldn’t learn how to get back up. We mistakenly cast failure in a negative light when it’s actually positive. The only true failure is not learning and growing from it.
  • It’s a waste of your time and talent on earth — We have one shot at this life (depending on your worldview). One chance, to use the skills, strengths, talents, time and energy you have. You’re a steward of those natural resources. Use them wisely and don’t squander them by never investing them in something worthwhile.
  • You’ve actually guaranteed your failure — If you never try, you fail 100% of the time. So the odds are better to try and fail than never try. I’ve found a large part of success is simply showing up, stepping out and taking the chance. Doing so means you increase the odds just by taking that one step out into the unknown.
  • Regret is a tough pill to swallow and irreversible — The top regret of the dying is “This was the most common regret of all. When people realize that their life is almost over and look back clearly on it, it is easy to see how many dreams have gone unfulfilled. Most people had not honored even a half of their dreams and had to die knowing that it was due to choices they had made, or not made. Health brings a freedom very few realize, until they no longer have it.” I’d rather try and fail miserably, then live with that kind of regret personally. Regret motivates me almost more than the rest combined.

OK, heavy stuff, I know … but now let’s unpack the reasons I hear or see (and have used myself) for why we never try.

3 Common Reasons We Fear Failure:

  • Fear of loss — When starting iThemes, it was health insurance and financial bankruptcy potentially. I had a great job, that allowed me to do what I wanted on nights and weekends. I could also lose credibility and relationships and my reputation. To me, those were early fears for me.
  • Fear of embarrassment — I probably live with this one more than anything, it goes: What if I fail and everybody labels me a failure? In eighth grade it was making the team but then looking stupid on the court. So I quit.
  • Fear of success — This is one I typically think of the least. I try because I can envision success and am typically energized by it. But I understand. It goes, if I submit this book proposal and it is accepted then I’ll have a ton of hard work and deadlines.

Ideas for What To Do About Those Fears

  • Take a small baby step toward it to build confidence — I wrote about Eating the Elephant (aka tackling any huge project or task previously here. What is the easiest, low risk step you can take in the direction of your goal or dream? Take that one itty bitty step. Then take another. Then another. (It eventually worked for Bob!)
  • List our your emotions and why exactly you’re afraid — Too often we let fear paralyze us without truly defining what the exact fears are. Listing them out in detail can often be the most therapeutic way to deal with them. And also realize how trivial or small they actually are.
  • Do a Pro Forma — This is more intellectual, than emotional, but is a great exercise we’ve done when we’re considering big audacious projects. When you know the spectrums of the cost and the reward, it helps formulate your gut response of courage.
  • Identify your roadblocks and start blowing them up — I read recently that exactly (just can’t remember where I saw it — I think Strategic Coach). But the idea stuck to me … find the things stopping you from doing what you want and just systematically eradicate them.
  • Enlist some help — For many entrepreneurs like myself, it was having partners. Just having other people involved in the undertaking gave me more confidence and lessened my fears. For any endeavor I take on now, I ensure my wife and life partner, Lindsey, is enlisted and supportive before starting.
  • Talk to someone who’s done it before — I find other people’s stories and experiences fascinating, enlightening and encouraging. I typically realize there was some perspective I hadn’t thought about. And just knowing someone else had done it before, helps me get the courage and confidence to take the next steps. In entrepreneurship, it was watching both my grandfather’s build and run their businesses. And my business partners had also been in business for a number of years which helped immensely for me. They had experiences to share when I was walking into my personal unknowns.
  • Gather all the key resources to be successful — Change the odds by building a base to feel more confidence and to increase your chances of success like coaching, partners, moral support, money, whatever you think you need to be maximize your chances for success. (Caveat: Don’t let these things become excuses for paralysis either.)

What are your tactics for combatting the fear of failure? (Put them in the comments below.)

Two final thoughts to leave you …

They are really quotes that have stuck with me and motivated and inspired me to try and fail.

The first …

“The tragedy of life is what dies inside a man while he lives.” -Albert Schweitzer

I ache when I think about the world-changing innovations, inventions, businesses, causes, actions that humans over the history of the world never attempted — the immense opportunity that lived in so many but died with them. How much better would the world be if we had tried and taken one bold step out into an unknown?

The second is longer but equally motivating and awesome to me …

“It is not the critic who counts: not the man who points out how the strong man stumbles or where the doer of deeds could have done better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly, who errs and comes up short again and again, because there is no effort without error or shortcoming, but who knows the great enthusiasms, the great devotions, who spends himself for a worthy cause; who, at the best, knows, in the end, the triumph of high achievement, and who, at the worst, if he fails, at least he fails while daring greatly, so that his place shall never be with those cold and timid souls who knew neither victory nor defeat.” –Teddy Roosevelt

Live in the arena of life. Take a bold step into its center stage. And dare to be great.

Share this post

3 thoughts on “Overcoming Your Fear of Failure

Leave a Comment