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I'm Kelly - the founder of She Is Fierce! and your host on our blog featuring stories and wisdom from fierce women all over the world! 


#45: How to Avoid Fear of Failure and Overcoming Challenges

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I’m so happy to be back with you today for the next episode in our popular new Summer School series, inspired by our sister company, Heirloom Leadership & Learning Co!

Since we started this series, we’ve explored what it means to follow your passion and purpose, how to start your own business or side gig and how to build a powerful personal brand and a business brand that connects with your ideal audience.

Today, we’re going to talk about a subject that comes up a lot at our live events, in my consulting and coaching, with speaking audiences and even just in private conversations.  


How to ‘Avoid Fear of Failure and Overcome Challenges.’


Before we jump in, I want to remind you that if you’re struggling with fear of failure or specific challenges in your life right now and need a full clear-out and rethink… you can download our completely free Passion & Purpose Challenge right now at

If you haven’t done so already, go grab that now!

So, let’s jump into this and talk about fear of failure (or even the fear that others might think you failed) – and how to overcome challenges in your professional or personal life.

First, recognize that fear of failure is holding you back.

Even if you are the wildest, boldest, most up-for-anything person, I can almost guarantee you have a story about when you didn’t even try something that you really wanted to do… or maybe you’ve been sitting on an idea for a long time and just haven’t been able to get yourself into the right frame of mind to get started.

This fear can manifest in so many ways and in so many different situations – for some, it’s the expectations their parents put on them or they have put on themselves for so long, they can’t even remember why…

For others, the fear of failure is situational – maybe it’s starting a business for the first time after years in corporate, or putting themselves out there as an expert or speaker publicly – risking that someone might think they are ‘not good enough’

And sometimes, and this can be the hardest one to overcome, it’s because they’ve gone out on a limb before and tried something daring or told others about their dreams and then… actually failed. 


Do any of these sound familiar to you?


  • Do you have the weight of your family or culture’s expectations? 
  • Do you believe that you have high potential and fear not living up to it?
  • Or, have you tried something really hard before and just not been able to hit your goals – maybe you were close, maybe you were far away from your goal – either way, if you feel like you have failed before, it can be really hard to have the courage to try again or tell others you’re going to try something new.


All of those situations are so relatable.  We have all put incredible pressure on ourselves at times – as professionals, as partners, as mothers or caregivers, as friends, as students – or in any other area of our lives!

Today, I want to talk through some of the lessons I’ve learned to overcome this fear, and some of the powerful examples I’ve seen of women who chose to take a challenge head-on and killed it!


So, first, let me share a story about a time I was experiencing fear of failure. Now, I wouldn’t even have described it that way… but I can tell you with absolute certainty that fear of failure was holding me back.

If you know me well, you know that I have always been passionate about supporting women and elevating women’s stories – even as a kid and young woman, I would get really upset on behalf of my friends when they didn’t see their own potential or would talk down about themselves.

As a young adult I worked in TV and digital news, and I started pitching the idea of highlighting stories of inspiring women even as an intern at a local TV station, then as an Associate Producer at a local TV station, then as a Producer for an international TV Network, and in every role I had, the idea was shot down by someone higher up.

It’s hard to believe now, but I started my career before the #MeToo movement took off and before women’s groups and women’s economic power were as respected as they are now… and I say that with the recognition that we still have a LONG way to go!

So, for YEARS, I knew what I was passionate about and was asking for permission from someone else to take on my passion and create something meaningful highlighting women’s stories.  

I even considered doing ‘something of my own’ to do this… but I never took myself seriously enough then to try it.

Now, with the space of time, I realize that it was mostly a fear of failure. I knew what was possible, but I was afraid I couldn’t do it on my own and because I felt comfortable in the roles I was in, I chose to stay with the comfort instead of embracing risk.

It makes me sad now to think that I could have started She Is Fierce! or something like it years before I actually did!  When I finally took the leap, I absolutely failed in different ways along the way, but I am so glad I followed my purpose – I am now almost nine years into this powerful mission!

So, what advice do I give women in our community on how to overcome their own similar fear of failure – that is keeping them from getting started?


Here are a few practical steps you can take to work through your fear:


#1 – Understand that we all experience this to some degree

Even those with the most incredible success stories have their own versions of my story… you are not alone, and that is a beautiful thing!

If your fear is around a business endeavor, I recommend listening to the podcast ‘How I Built This’ – you will hear stories of so many people who doubted themselves and still found success.

At our live events, and even here on our podcast, I ask our guests to share their personal stories and the challenges they overcame.  

More often than not, I am surprised by how much these fierce women we are featuring have overcome – and how much they have failed their way to success.

The dozens and dozens of women we have featured with incredible credentials and impressive success stories have given me a glimpse into the reality around how much failure (small and large) goes into following your purpose successfully!

#2 – You aren’t the sum of what you have already done.

Often, people fear failure because they don’t feel they have the credentials, the connections, they don’t look right or whatever it is they are telling themselves they lack.

Many people become ‘success stories’ later in life because they have finally stopped worrying about other people’s opinions of them along the way! 

Wherever you are on your life journey, I encourage you to do a simple exercise – put yourself in the mindset of yourself at ninety years old. 

Look back at your life – what do you wish you had done? 

Whose opinions of you do you wish you had dismissed much sooner?

Now – be honest with yourself – do you believe that if you continue on the path you are on today, that you will be looking back with no regrets?

If the answer is no, that’s ok – truly! But it does mean you have some stuff to get started on – and only you know what exactly that is!

I hope it will serve as a reminder that you can walk a new path any day – you just have to choose to follow your purpose.

#3 – Learn from past failures.

Every failure is an opportunity. It may not feel that way in the moment, but you have probably already lived through some failures that have ultimately enriched your life by forcing you to think differently, take chances, ask for help or give more of yourself.

None of us want to fail publicly, but it is a much sadder thing to succeed at not trying and wonder what could have been.

A couple years into She Is Fierce!, I was still a young mom with two very small children trying to build a business centered on women and follow my purpose. If you’ve heard my story before, you know I started with no – and I mean NO – investment money and no pot of cash to fund the business.

As we started to grow, I was thrilled to find myself out of the first couple years of uncertainty and actually hitting six figures in the business comfortably.

But – to this day, in that sudden comfort zone, I made one of my most ridiculous financial decisions that cost me thousand dollars on basically nothing.

For an event we were holding, I guaranteed hotel rooms thinking we would have lots of people who would want to stay together in a specific place… the event sold out fast, but almost nobody wanted to book rooms in the fancy luxury hotel I had guaranteed.

I ended up losing seven thousand dollars in room guarantees – and being stressed about the loss instead of celebrating the success of the event!

The loss was a total bummer, but it also didn’t break the business – and that was something to celebrate in itself – since a few years before it would have meant I would have been out looking for a job!

And, I learned a lot about smart commitments vs. foolhardy commitments – that has served me well in much bigger deals and helped protect me from much greater losses since then!

#4- Your challenges can also be opportunities

Just like my story about losing money on a hotel guarantee, some of the best things that have happened to me and so many others have come from the hardest times.

When things get tough and you’re wondering why everything feels like a challenge, remember that – when framed correctly – almost any challenge can turn into an opportunity.

Years ago, I had someone I had partnered with turn out to be very different from who I expected them to be.

I was upset with them – but even more angry with myself.

I had ignored signs because I so wanted to have someone else to do the hard things with.

It took me a lot longer than it should have to realize that when that partnership ended, I was able to make more money, increase my impact and keep my focus on the reasons I had started the work in the first place.

If you tend to dwell on the things that haven’t gone your way, I encourage you to try a simple exercise of writing down what came after the hard time, the breakup of a relationship, the public failure.

You can write the hard things, but don’t forget to include all the positive things too!


  • Did you learn something about yourself?
  • Did you build a new plan that didn’t include those previous mistakes – and end up with a better result? 


Sometimes, we don’t even give ourselves credit for the amazing final outcome because we are still dwelling on the hard times we went through to get there.

Sit with the great things you have done for a while – and recognize the challenges you have already overcome to get to where you are today!

Every one of us will be faced with challenges in the future, but our outcomes are not defined by the challenge – they are defined by our reaction to the challenges.

And finally, 

#5 – Remember: Progress, not perfection.

There is no shame in not being perfect – and no shame in being a new beginner.

My favorite kinds of people are lifelong learners – all you readers and joiners and podcast listeners out there who are constantly exploring the world and thinking about what is next.

That is a beautiful place to start any journey from. Recognize in yourself the ability to embrace wonder and to think big about what is possible.

Perfection is subjective – if you try to hit it, you will still have others who think you aren’t perfect ‘enough.’

Instead of focusing on your idea of perfection, embrace the progress along the way! Every time you fall down and get up again is something to celebrate!

You have so much within you and I hope this episode has given you some inspiration to embrace the journey – ups and downs – and know that every true success story has an unpublished backstory behind it filled with mistakes, failures and everyday challenges along the way.

Now – If you haven’t done so already, go grab that completely free Passion & Purpose Challenge at and use it as your guide… or check out our Membership at to access our library of Heirloom courses which walks you through so many of the foundational skills you need to succeed and go deeper on building a business or career you love. 

Plus, inside our membership you have access to dozens of other workshops, Heirloom courses, mentor replays and more!

See you right back here next week with more from our Heirloom Summer School series!

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