How to Overcome the Fear of Failure

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What would you do if you knew you couldn’t fail?

If you, dear reader, will grant me a moment, I would like to be very blunt at the outset of this article:

I hate the above quote.

I understand that it is a commonly-uttered phrase intended to inspire and motivate people to dream big, take risks, shoot for the stars, and a whole host of additional clichés.

Reality check – everyone fails. All the time.

What if, instead of the above quote, people asked, “What would you do if you knew you could succeed?”

I prefer the turn of phrase above for two reasons. First, it is a question with an affirming, positive slant. Second, it does not erroneously assert that failure and success are somehow mutually-exclusive, as if failure may not be present on the path toward success; instead, it emphasizes that success is always a possibility, despite one’s past failures.

There is a reason the notion of “failing forward” has stuck around in the past decade since John Maxwell wrote Failing Forward: Turning Stepping Mistakes Into Stepping Stones For Success:

The difference between average people and high-achieving people is their perception of and response to failure.


If society better-prepared us to expect, even embrace failure, and keep pressing on, what fantastic successes might we experience?

A Modern Case Study

Last week, I read an incredible story about Taylor Rosenthal.

Rosenthal isn’t afraid to fail. The 14-year-old from Opelika, Alabama, is too young, optimistic, and busy to be afraid to fail.

A bright student and average baseball player, Rosenthal is the founder of the start-up company RecMed, which specializes in the deployment of medical supply vending machines.

His idea was basic, yet inspired. Explained Rosenthal,

“Every time I’d travel for a baseball tournament in Alabama, I’d notice that kids would get hurt and parents couldn’t find a band-aid,” he said. “I wanted to solve that.”

His initial thought was to set up a pop-up shop at the tournaments to sell first-aid kits. He tried it and quickly realized it wasn’t the best model.

“We noticed that it would cost too much to pay people minimum wage to sit at tournaments for six hours,” he said. Then the vending machine idea struck.

Rosenthal sketched a design and consulted with his parents, both of whom work in the medical industry.

By December, he had a working prototype and had acquired a patent.

Users pick from two options: prepackaged first-aid kits for dealing with issues like sun burns, cuts, blisters and bee stings (they run from $5.99 to $15.95). You can also buy individual supplies like band-aids, rubber gloves, hydrocortisone wipes and gauze pads, which cost $6 to $20.

Rosenthal hopes to start deploying the machines this fall. He said they make sense at “high-traffic areas for kids” like amusement parks, beaches and stadiums.

He already has an order from Six Flags for 100 machines.

RecMed will make money by selling the machines, which cost $5,500 apiece, and through restocking fees for the supplies. Rosenthal said he’s also open to putting advertising on the machines.

Needless to say, Rosenthal’s first business plan appears to be a wild success. Rest assured, he will probably fail majorly at some point in the future. But for now, he is seizing his opportunity, even turning down a $30 million buyout offer, because he isn’t afraid to fail.

Naturally, Rosenthal’s teacher, Clarida Jones, has taken notice of her star student’s fearlessness. Said Jones,

It has been amazing watching Taylor grow over the past year into this confident and amazing business man. Even with all of his success, he remains humble and ready to help others. He’s just 14. Bill Gates should be worried.

I doubt Mr. Gates is worried, but he undoubtedly should be impressed, as Rosenthal’s entrepreneurial pursuit is representative of the kind of educational outcomes that Gates hoped to procure through his educational reform efforts.

Photo credit to CNN Money
Taylor Rosenthal with the RecMed vending machine. Photo credit to CNN Money

It is easy to criticize Rosenthal’s rejection of a $30 million buyout. After all, he could somewhat lavishly off a very modest one percent annual return on his spoils. I suspect the rejected offer was less about the money and more about the thrill of the chase and youthful naiveté.

On the other hand, it is hard to fault Rosenthal. He can afford to take a big risk at this stage in his life. He does not have mortgage, auto, credit card, and student loan bills. He has not yet been jaded by the financial obligations of adulthood.

Perhaps he does not fear failure because he hasn’t yet been programmed to expect it.

Four Roots of the Fear of Failure

Pause for a moment and compare several of your grandest endeavors with that of Rosenthal. If you are like me, your story is probably much different. Perhaps you were programmed to fear failure, and it held you back in the past. Or worse, fear of failure may be holding you back from new pursuits in the present.

I consider the following to be the Four Roots of the Fear of Failure:

1. We fear getting started

Mark Twain said, “The secret of getting ahead is getting started.” It is a shame that Twain did not also share the secret of getting started!

As an entrepreneur, emulation of others is always an effective way to start.

For example, I followed other bloggers’ work extensively for months before beginning FinanceSuperhero. My goal was to observe the writing qualities that kept thousands of daily readers coming back to their websites on a weekly basis. I even studied the guides on how to start a blog written by FinancialSamurai and Mr. Money Mustache before launching my own blog.

Despite a reliable framework to follow, I felt a bit uneasy, at times, throughout the process. However, I was reminded of an important principle in the process: What we fear rarely, if ever, comes to pass; at the same time, if we do not start, we will never know what might have been.

2. We fear that failure is fatal.

It is normal to fear making a mistake, as mistakes will certainly happen. Yet despite that nagging inner dialogue, the repercussions of our mistakes are rarely fatal.

Billionaire Mark Cuban is a great illustration of this principle. In the early 1980s, the soon-to-be-billionaire was fired from his position as a salesperson for Your Business Software, a local Dallas retailer. Why? He was reportedly meeting with a client to develop new business instead of opening the store.

The road that followed was long and winding, but Cuban’s mistake would not define him.

3. We fear what others may think of us if we fail.

I must confess that I am very guilty of this from time to time. However, by simply being mindful of this trend in my own life, I am able to remain focused upon my own values and act on them rather than out of fear of what others may think. Besides, can any of us really purport to know what others think?

At every step of the way, someone will criticize your decisions and urge you to go in a different direction. Courage stems from the conviction to hold fast to your chosen path.

4. We fear the path of struggle and difficulty.

Just as assuredly as you will experience your share of failures, problems will arise. The key to overcoming them is learning to embrace challenges and view them as opportunities.

It is easy for me to say this. My natural personality leads me to chase challenges and run head on into difficulty. I feel most alive when toiling through adversity.

If you are naturally prone to fear difficulties, you’re not alone. But you can begin to ease your fear by taking a series of small steps.

How to Defeat Your Fears

In my experience, fear is like a boisterous middle school bully. It is threatening on the surface, yet it fades quickly when confronted by direct action.

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No article on overcoming the fear of failure – whether it be personal, career, or financial failure – could be complete without referencing perhaps the best-known quote on fear. In his inaugural address in 1933, President Franklin D. Roosevelt spoke the following immortal words:

So, first of all, let me assert my firm belief that the only thing we have to fear is…fear itself — nameless, unreasoning, unjustified terror which paralyzes needed efforts to convert retreat into advance.

If you fear failure, heed the timeless advice of FDR: advance!

Notes and Disclaimer: The links contained within this article are affiliate links. FinanceSuperhero only recommends quality protects which will serve to help you improve your financial position.

All investments feature risks. You should consult a qualified professional before entering into any investments that you may not understand.

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Readers, how have you learned to overcome fear of failure? Have your past failures been the launching board for your greatest successes?


31 thoughts on “How to Overcome the Fear of Failure

  1. “Perhaps he does not fear failure because he hasn’t yet been programmed to expect it.” – Wow – is that a great line and so true! That was an amazing story! For all those who are “down” on our youth, there are some amazing kids out there!
    I think I struggle most with this -“We fear what others may think of us if we fail.” I agree with you and have finally decided that I don’t need to really worry what others think. It took a long while to get there though! We may need to stick together on that one!
    Great post!

  2. Fear is a strange things. It makes that we prefer not to change, unless where we are now puts us in great great danger.
    Being aware about our financial state and the possibilities there are, makes me a little less fearful. We dare to invest, change jobs,…

    The Taylor story is really amazing. Rejecting a 30 Mio offer… That takes courage to do so!

    1. Like GS said, I still think Rosenthal’s decision is nuts. On the other hand, I wish I had even half of his courage and bravado.

  3. Great post and tips on how to overcome fear. Important to not have a life paralyzed by fear. Can’t believe he turned down $30 million though! On the face of it that sounds borderline insane.

    1. As I was reading the article about Rosenthal for the first time, I did a double take when I read about the $30 million dollar offer. Though he might not be the greatest at math, the kid has guts!

  4. John C Maxwell has some great ones, doesn’t he? Along the same lines, there’s a quote I once read from Peter Drucker that went something along the lines of “entrepreneurs aren’t great risk takers, they are actually great risk calculators”. To me, I interpreted this as greatly increasing your chances for success by knowing what you’re getting into instead of just blindly following your ambitions.

    1. I aim to read a new John Maxwell book every quarter, MMD; like you said, he has put out some excellent books over the years.

      Risk is a fascinating phenomenon. I’m currently reading a great book, “Dollar Logic,” which analyzes the true nature of risk in personal finance and investing. I already feel that I am becoming a better risk calculator.

  5. At work I often hear the phrase ‘fail fast’. Not surprisingly, failure at work is not a bad thing – it’s expected. And when new employees realize this, they suddenly have new confidence, which leads to more success, and a better business.

    Lingering in failure when something is obviously not working is bad. Not realizing why you failed and making the same mistake over and over is not OK.

    I’m taking this same approach with my side hustles and blog. No pressure means I’m having a good time. Eventually I think success will come, whatever that means, but in the meantime I fully expect to fail multiple times.

    1. Ty, it sounds like your company has crafted an enviable culture for your team. I am puzzled when I hear friends speak about the toxic cultures of fear and pressure in their workplaces; more and more, I am learning that leadership sets the stage for culture.

      I have no doubt you will experience great success with your blog. Your openness and careful analysis in your writing will help you continue to draw new readers.

  6. We are designed to fail. Failure isn’t the problem, just how we react to it. I don’t enjoy failure, but there is simply no better learning tool. Hopefully we can learn while watching others fail but it simply doesn’t hit home like our own failures.

  7. There’s a saying about how we obsess about how others judge our failures. But meanwhile those others we worry about hardly notice us. Therefore they make no judgements because we don’t matter to them. At first this seems like a cold idea. But I find it comforting.

    1. It does seem rather cold, but I think it is very accurate, Mrs. Groovy. We tend to believe that we are the center of the universe and fail to account for the fact that others are just as self-absorbed as we are. Thanks for sharing this great connection!

  8. You know what scares me more than failure? Not trying. There are a lot of things I was set up to fail but overcame by perseverance, hard work, and a lot of help from the guy upstairs.

  9. I am a proud dilettante in many areas of my life. Once I stopped being a perfectionist, I was more willing to try things. I don’t have to be the best at something to enjoy it and to profit from it. This pivot has made an enormous difference in my happiness and ventures. I’ve also learned so much from failures. I always force myself to take time between relationships because I like to examine what choices I made that did not serve me well. It was hard to take the time before asking out my current girlfriend, but I’m glad I did. She got a much healthier me as a result.

    1. From one perfectionist to another, I understand how crippling it can be at times. I am learning to be more introspective and simultaneously accept that I will fail often.

  10. I use the same strategy for getting over failure that I do for dealing with success. I don’t let either one dictate my emotions. I try to stay calm no matter what the outcome.

    When I first started a business years ago, I would get real excited when things would go well. And I would get real depressed when things would go badly. That up and down was too much to deal with.

    Instead, I learned to stay focused on my goals and the process of moving forward.

  11. The worst thing you can do in life is not try. We all fear failure but you get nothing out of life if you take no risk. I had a fear of starting a blog and what others would think of it but I am glad I overcame that fear and just went with it.

  12. This reminds me of the great quote by Ira Glass, the “Nobody tells beginners this…at first there is a gap between your taste and your skill. Your taste is what keeps you going”

    I’m definitely guilty of being afraid to invest. Several months back, I finally got around to setting up a Roth IRA and examining my 401k more.

  13. The fear of investing is a real problem, a lot of people read and learn but are scared to take action rendering the knowledge close to useless

    Fear still prevents me from taking risks, I am working slowly to overcome it and starting a blog has taken a lot of the fear away already

  14. Thank you! I’ve always hated that quote. Perhaps it’s just because we’re in special circumstances (both my husband and myself have multiple chronic health conditions). So the assumption that we couldn’t fail is just… implausible. We have so many extra obstacles to overcome. Including depression, which makes the fear of failure paralyzing at times. Trying to pretend it doesn’t exist is inconceivable to me.

    I agree that the key to trying is accepting that failure is an option — it’s just something that you’ll use to learn how to do better next time. It’s something you have to look at as a way to build to success rather than proof that you shouldn’t try again.

  15. I personally think its necessary to fail in order to succeed. Its not easy to be succesful on your first attempt at anything. Failing is just part of life and I know I wouldnt be where I am today if it wasnt for all my failures.

    I embrace failure!

  16. Failure is good in all parts of life, investing yes. Money in general. You can even apply it to relationships, if your first girlfriend doesn’t work out, you can take the lessons learned from that into future relationships.

    I try to think very logically about our goals. I know that if we keep saving and investing, we will reach our FI goal.

    If we keep writing good content on our blog that’s worth following, people will continue to read it and be engaged.

    If we keep being healthy we will lose weight and have good bodies.

    Those types of goals just have setbacks, we will get there eventually.


    1. As always, excellent thoughts, Tristan. As Winston Churchill said, “Success is not final, failure is not fatal: it is the courage to continue that counts.”

  17. Half the battle is starting! Being fearful of the unknown is normal especially if you are comfortable in your current situation.
    I know when I changed jobs from what I was doing for 9 years on good money to a part-time job with hopes of being successful it was scary! I had one kid and another on the way!
    Sometimes you have to take a chance and for me it paid off. I was fearful but knew I had to make a change to make me happy.
    I look back now a realize that if it all did go pear shape I could have either kept plugging away or found another job…. no big deal. 😉

    1. Thanks for sharing your personal experiences, Ray Ray. I can completely understand the reasons for your fear in that situation. I’m glad it didn’t move you into a state of inaction!

  18. Fear can definetly paralyze you from taking action. Perseverance comes from taking action in the presence of fear. I think we all struggle with fear of failure as you outlined in this post. In my life, I find facing fear builds my ‘internal muscles’ so when similar adverisities occur, we are less fearful of them and more willing to ‘advance’.
    Good post.

    1. Wow, I think you just explained the crux of the issue far better than I did in my post, Pamela. Perseverance DOES come from taking action in the presence of fear. I sometimes have difficulty being bold and taking that first step, but you are absolutely correct – it helps us to build strength.

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