Kickstart Your Courage: A Beginner’s Guide To Conquering Fear Of Failure


It can strike the best of us, this pesky ‘fear of failure.’

One minute you’re dreaming big—like Elon-Musk-on-a-space-odyssey big—and the next, you’re shrinking back into the cozy but oh-so-limiting cocoon of your comfort zone.

Imagine you’re teetering on the brink of starting something fabulous;

  • a giant leap of a goal,
  • a brain-tinglingly exciting new hobby,
  • finally sorting out that jungle you call a garden.

Then, like a bad movie cliché, in swoops the fear fiend, hissing doubts in your ear.

  • “How in blazes will I do this?”
  • “What if it’s a cataclysmic flop?”
  • “Who do I think I am?”
  • “People will point and laugh!”
  • “Maybe I’ll start… someday.”

And just like that, that fabulous dream vaporises.

Comfort zone: 1—You: 0

We’ve all heard those heart-wrenching tales of regrets from the nearly-departed. But you don’t have to be on your deathbed to kick yourself over missed opportunities.

We soon get over those boo-boos and blunders when we pursue our passions. It’s the ‘what ifs’ and ‘if onlys’ that stick around like a bad smell.

Take aging, for example

At some stage you’ll realise some dreams are now just that—dreams. That hip isn’t what it used to be, and your back does a better impression of the Leaning Tower of Pisa than supporting ambitious endeavours.

So why the hesitation now?

It’s often fear that puts the brakes on our wilder aspirations:

Fear of failure, fear of success (yes, it’s a thing), fear of being judged, fear of stepping outside our snuggly comfort zones.

Read sign that says great things never come from comfort zones

But we grow only when we dare to step beyond the familiar.  Stepping out of your comfort zone isn’t just about changing your socks; it’s about embracing the fear of failure with open arms—and maybe a few a dance moves to keep things lively.

Embrace the “Oops” Mentality

“The greatest mistake you can make in life is to be continually fearing you will make one.” – Elbert Hubbard

Instead of viewing failure as something to be feared, why not reframe it as an opportunity to learn and grow? One of the nifty NLP concepts is: ‘There’s no failure, only feedback.’

It’s about looking at mishaps, setbacks and mis-takes as learning opportunities rather than epic disasters. Branding something a ‘failure’ is like hitting a brick wall at full speed. Not fun, and definitely not productive. Just say, “Oops, another learning opportunity!” And move on.

Before becoming one of the most successful authors of all time with her “Harry Potter” series, J.K. Rowling faced numerous publisher rejections. She was a single mother living on social welfare, struggling to make ends meet.

Despite facing financial hardship and her fear of failure, Rowling continued to persevere, pouring her heart and soul into her writing. Her resilience paid off when “Harry Potter and the Philosopher’s Stone” was finally published in 1997.

Rowling’s determination and self-belief have allowed her to overcome setbacks. She’s not only a literary icon, but also a billionaire philanthropist. She faced her own daunting fear of failure head-on.

This is a great example of following your passion and focusing on the result, regardless of your present circumstances. Whereas, all too often, we allow problems and obstacles to consume our attention, diverting us from our dreams.

You might never have heard of Blake Mycoskie, the founder of TOMS Shoes. Mycoskie created a business model that was unusual at the time: for every pair of shoes sold, TOMS would donate a pair to a child in need.

This ‘one for one’ concept didn’t rely on mainstream opinions or traditional business models. Instead, it tapped into a unique niche of social entrepreneurship, combining business with philanthropy.

Mycoskie’s success was driven by the novel idea itself and its appeal to a growing demographic interested in ethical and socially responsible consumption.

man's hands holding a pair of toddlers brown shoes

Wilma Rudolph, a black American woman and the 20th of 22 children (yikes!), provides a remarkable example of overcoming personal challenges. Born prematurely and afflicted with polio as a child, Rudolph wore a leg brace and faced significant mobility challenges.

Despite these obstacles, she worked tirelessly to strengthen her leg and eventually shed the brace. Rudolph’s determination led her to become an American sprinter and Olympic champion, winning three gold medals in track and field at the 1960 Rome Olympics.

“My doctor told me I would never walk again. My mother told me I would. I believed my mother.” ~ Wilma Rudolph

Other Wilma Rudolph quotes

Her story is a testament to resilience, determination, and personal drive.

So what drives you?

Are you inspired by stories of perseverance and want to create your own success story?

Embrace your imperfection

You don’t have to be perfect to overcome your fear of failure, you just have to be human (you are human—right?) We all have our vulnerabilities and by embracing imperfection, you can unlock a whole new level of authenticity and connection.

It may sound counterintuitive, but it’s true. Being vulnerable helps us connect with others on a deeper level and find new opportunities for personal growth. It’s time to embrace our imperfections and let our true selves shine.

What about setting more ‘comfortable’ rather than ‘uncomfortable’ goals?

Great question! Sometimes, achieving your ultimate goal and living your passion can seem so out of reach it feels overwhelming. And if your goal feels overwhelming, what do you think your chances of achieving it will be? You’ll be too stuck in overwhelm to move forward! And if you don’t achieve it, it’ll just cement your fear of failure.

That doesn’t mean you should give up

It’s important to still keep your true passion and end result in mind. You can set an interim or transitional goal. Something that’s a stretch, but doesn’t feel mind-bogglingly hard.

“I can accept failure, everyone fails at something. But I can’t accept not trying.” ~ Michael Jordan

For example, let’s say you want to go to university and get a degree in psychology. However, you hated school and left at 15 with no qualifications. Now you’re 45 and don’t know if you could hack the study, examinations etc.

Yet you’re fascinated by the subject and would love to help people. Studying for a degree feels overwhelming. So you could find a course that scares you a bit, but you know that if you apply yourself, you can achieve it. It might involve just taking one university paper part-time, committing to one term or completing a short course about human behaviour.

You could take an online course that will give you a qualification that will contribute to, or move you towards your end goal.

Here’s a curly question to ponder: ‘What would I do if I was guaranteed success?’ It’s a twist on the old ‘What would I do if I knew I couldn’t fail’, but it gets the cogs whirling.

What’s your heart yearning for?

(OK now close your eyes and ask your heart that question.)

Listen carefully for the answer.


  • You want to run a marathon, but have the fitness level of a couch potato?
  • You’d like to launch a business, but you’re terrified of giving up the 9-to-5 financial safety net?
  • You’d love to get a degree, but doubt your academic ability?
  • You’re dreaming of globetrotting to exotic locales, but you’ve barely left your postcode?

Look at all those dreams with their big, scary ‘buts

I don’t know—what is it you’d love to do that would take you out of your comfort zone and into another part of town?

Whatever it is, I expect someone else has already done it. And if someone else has done it, then you can too.

Those ‘buts’ are like speed bumps—they’re there, they might slow you down (that’s what speed bumps are supposed to do!), but they’re easy to cross when you approach them properly. If you’re truly passionate, no speed bump will stop you.

Remember your toddler days?

Think back. (Yeah, Ok you might not remember, so just watch a toddler for a couple of minutes!) As a wee one, you saw something colourful or shiny, and you were like a mini-missile zooming towards it.

There was no way a piddly little road block would hold you back. Obstacles? Pfft, mere trifles. You’d find a way—over, under, around or through.

determined toddler crawling after a toy.

Well guess what?

That single-minded little kid is still in there, but now with a truckload of skills and abilities.

Plus, you can walk without falling over or banging into something—bonus!

“Failure should be our teacher, not our undertaker. Failure is delay, not defeat. It is a temporary detour, not a dead end.” ~ Denis Waitley

Dealing with the fear fiend

Don’t just shove that fear into a dusty corner of your mind. Drag it out into the harsh light of reality and examine it under a spotlight.

Jot down every fear, every stumbling block. When they’re all swimming around and crashing into each other inside your head, all you experience is overwhelm. Problems are a lot more handleable when they’re just words on paper.

They seem less like towering monsters and more like… well, words. Use my Overcoming Overwhelm process to help with this.

Overcoming the fear of failure

Plan your way around those fears like you’d plot a holiday escape.Goal Setting Book

  • Chat with a trusted friend and get their input.
  • Get a coach to help and guide you (Hellooo—pick me!)
  • Warning! Shameless plug alert: Get my Goal Setting book covering everything you need to know to achieve your goals and avoid fear of failure. (You get the workbook for free!)

And remember, you don’t have to conquer all your fears on day one.

Preempt some troubles and improvise as others pop up.

Success isn’t a straight, wide road

It’s a narrow, winding road with lots of ups and downs and sometimes it even doubles back on itself! Sometimes, there’s not even a road—or a dirt track— especially if you’re a trailblazer! Even knowing this will help you cope when things don’t go strictly according to your plans.

Visualise yourself overcoming these hiccups, review what you’ve learned in the process, and keep pushing forward.

The alternative?

You’ll join the ‘I tried, but oh well, obviously it just wasn’t meant to be’ chorus.

Why settle for that when, with just a little more effort, perseverance and kicking that fear into touch, you could join the likes of New Zealand’s own Sir Edmond Hillary. As the first person to reach the summit of Mt Everest, he exclaimed “We knocked the bastard off!”

Ready to take the plunge and overcome your fears? Try this:

Change the question

Instead of telling yourself why something is doomed to failure, or why it’s not going to work, try something different. Ask yourself ‘How can I make it happen?’ There are a number of people who have been on my longer (6 and 18-day) courses, who initially had various excuses: reasons they couldn’t attend!

  • I’ll never be able to get the time off work
  • I don’t have the money
  • The household will fall apart if I’m not there
  • The kids won’t cope without me
  • My partner will be unhappy about me being away.
  • I’m not sure I can cope with such a lot of learning.
  • I’m worried in case I don’t fit in with the other participants

To each I’ve suggested they ask the ‘how’ question, and notice how they get different answers:

  • How can I get time off work?
  • How can I find the money?
  • How can I make sure the household runs OK when I’m not there?
  • How can I ensure the kids can cope?
  • How can I reassure my partner about being away?
  • How can I cope with such a lot of learning?
  • How can I stop worrying about fitting in with the other participants?

How questions force the mind to brainstorm solutions. Some participants have had their company pay for the course—and given them the time off work to attend.

Others have strengthened their relationships with their children and partner. Kids have thrived on being given more responsibility. And the people who were worried about fitting in have made lifelong friends with others on their course.

Watch this social experiment video conducted in New York

People from all walks of life write their biggest regret on a huge blackboard. (3 mins)

Go to the video link on YouTube and read some of the comments—and the replies to those comments.

Now imagine you have a blank slate

You’ve wiped away all the regrets and you’re starting today with a blank slate. What will you etch onto it?

It’s easy to wade through life’s could-have-beens, but here’s the game-changer: flip the script.

Imagine a life where those ‘if onlys’ transform into ‘I’m pumped, I dared!’ And the pure, unadulterated freedom it brings.

Envision your life, not as a series of missed shots, but as a spectacular adventure. It’s not about regret; it’s about stepping into a world where you own your story, facing fears with a rebel yell.

Picture the result you’re aiming for—whatever makes your heart sing. You’re not just a bystander; you’re the hero in your own epic tale. Each trip-up is a plot twist. Each fear faced is a victory.

“Fear of failure must never be a reason not to try something.” – Frederick Smith

Grab life by the throat

It’s your turn to transform that “maybe…someday” into “Woohoo! Look what I’ve accomplished!” When you reflect on this brief moment called life, it won’t be with a muted nod of satisfaction. You’ll be another legend who “knocked the bastard off!” earning not just applause, but a roaring standing ovation.

Alright, intrepid explorer of life, it’s time to unleash your innermost ambitions

Ever fantasised about becoming a salsa-dancing champion or writing the next interstellar adventure novel? Let’s see those vibrant dreams and audacious plans in the comments. Go on, you know you want to. 😜 Remember, throwing your goals out into the universe is the first step to making them a reality. It’s like a promise to yourself.

I can’t wait to read them.

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Tags: Goals, Motivation and taking action, Resilience, Thinking and mindset


  1. Caroline Gatenby

    Another awesome read Stephanie. Thanks for the gentle kick in the butt… Time to move out of the comfort zone. I’m off to put up my first add since moving house, so I can get on and do more of what I love x

    • Stephanie

      Yay! Go Caroline. ❤️ The thing is, you’re so great at doing what you love, it’s unfair to deprive the people in your new environment of your superb, wellness services. I wish you were a bit closer to me.

  2. Sharon Stannard

    Great article Stephanie. Loved reading it and ironically on the regret video you posted the first one related to artistic talent. Fear of failure has meant in recent years I have had 12 unfinished artworks – uncompleted, so they cannot be judged. This is going to be my year to get my art going!! Thank you for all your motivation to have the courage to move forward. xxx

    • Stephanie

      Thank you Sharon, I can’t wait to see some of your completed artworks. The thing is with any creative project, it will be judged — and so what?! Thank goodness we’re all individual and have differing tastes. Imagine the competition otherwise. 😊 The people who love your art will find it and it will delight them forever! ❤️


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