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One way to overcome fear of failure (and my failure experience)


Fear. Of. Failure.

It has such a presence in most of our lives, right?

The fear of failure has bubbled it’s way to the surface in my own life in these past few weeks, and of course, I’ve also heard the same fear from others come up a lot recently. I always find it fascinating how, as a coach, the things I’m going through are usually the same things my friends and clients are coming to me about, too. Funny how life works that way!

My own fear of failure has been coming out recently because I’m launching into an area that is unknown for me in my business. When I got back from SE Asia, my determination and drive to love my life was even stronger than it had been before. I’m not sure what shifted in me while I was abroad, but when I came back, I felt more fiercely devoted to my happiness than ever.

One of the changes I wanted to create in my life to be more aligned with my joy was to start doing live events, speaking engagements, collaborations, and live workshops. I absolutely love private coaching and my virtual programs, AND I wanted to add to my offerings to include more live, face-to-face interaction.

But … this is unknown territory for me. I’ve never really done anything like this.

I have built my virtual business from behind a phone and computer screen, and while I know deep down that it’s time for me to come out into the open more, I don’t know how this will all work.

Therefore, my fear of failure has been front of mind, and at times, has admitedly shaken me.

I am learning to navigate this time with compassion, deep self-care, and as much patience as my impatient self can muster.

I know that, like me, you may be experiencing your own fear of failure so I wanted to share a story with you about a time recently that I dealt with fear of failure in a really productive way. 

Let’s zoom back to September 2015. I had just launched Master Your Life, my most important piece of work I have ever put out in my life. I had spent so much time and resources on this launch, and not only that, I had truly poured every ounce of heart and soul into it. The program was an extension of myself – everything I had learned, everything I cared about, everything I wanted other women to know.

The first day it launched, 2 people signed up. 

And then… crickets. 

For a long time. 

I was crushed. 

I was ashamed. 

For days, I was spinning in my head and felt like a cloud was hanging over me at all times. 

And then one day, I was laying in my bed. Anxious, fearful, and defeated.

And I said to myself, Jamie, this is not how you want to feel, and not how you need to feel. Your fear is causing you to feel like shit and it’s taking you down. What are you so scared of? 

I realized I was so scared of failing, so I decided in that moment to “simulate” my worst case scenario. 

I laid in bed, and I said, okay, worst case scenario is that nobody signs up. I will have to admit to my friends, my family and my clients, that Master Your Life didn’t work out. I may have to cancel the program if I don’t get enough sign ups. I will have to tell the 2 people who signed up that it didn’t work out and apologize and refund them. I’ll have to admit failure to my business coach who put so much faith in me, and her and I will have to go back to the drawing board. I’ll have to find a way to make more money for the rest of the year.

And I noticed how my body felt as I went through all of these outcomes.

The most painful, squirming-in-my-body fear that came up? 

The embarrassment of telling my friends, family, clients, and even the public (on my website, etc.).

The embarrassment of publicly failing in such a big way. I had talked up this program for months, and I would have to tell everyone that it just didn’t work. The embarrassment.

And then I asked myself, what are you so scared of with this? What might they think of you that you are so scared for them to think?

And the answer here… they would look down on me. They wouldn’t see me as smart as they do now. They wouldn’t see me as successful, accomplished, or able to do anything.

And as I leaned into my actual fears… my body physically felt it. All the shame. All the squirming. All the discomfort in my body.

And I kept going like this…what is so scary about that Jamie? What are you trying to not have happen? What would be so bad if it did? And I kept letting my body feel it.

Here’s what became clear as I did this: It all comes back to love. 

We are all scared to not be loved and accepted. 


As I drilled into my fears, it all came down to one core thing: I want to be loved and accepted by people and I was scared that by failing, they would see that I am capable of failing and not love and accept me in the same way.

But such a beautiful thing happened as I did this exercise: 

Once I identified my core fear, I saw how crazy it was. I literally simulated the specific failure of this program, and through fully leaning into the feelings of failure, I began to see and feel the reality of how my friends and family would actually respond. 

They wouldn’t care. 

They would see me as a human being who has ups and downs, successes and failures. 

They would relate. Undoubtedly, they would relate. They have been there in their lives, too.

They would love and support me and make me feel better. 

They would love me just as much if not more. 

They would love me for being human and for having failures and for being real.

And most importantly, I could love myself fully even if I failed. I knew that I was just as worthy of a person, no matter what.

And then, my whole body relaxed. I knew I was safe. I could fail. I could have nobody else sign up. I could cancel the program if I had to.

And I would still be safe, and loved and adored. Both by myself and by others.

Everything relaxed, I could breathe again.

And I was free.

And you know what happened after that? I marketed the shit out of that program… from my heart. Not from a place of “I am so scared to fail so please please buy my program”. I marketed it from “I really believe in this, and here’s why, but I am not desperate for you to buy this because my self worth is okay regardless.”

And it worked. Tons of people signed up and it was the most incredible couple of months, guiding these women through something I cared about so deeply. But I strongly believe that if I had put out fearful energy, it would have been a different story.

So here’s my suggestion for you if you’re feeling scared to fail:

Lay down, in your comfy bed, and simulate what “failure” would look like in whatever area it’s coming up for you. Feel it in your body. Let yourself feel how dreadfully uncomfortable it feels. Cry if you need to, hold yourself, breathe through it.

And as you picture and feel your worst case, failure scenario, keep going deeper. Ask yourself, “and what is scary about that”? And when you get that answer, ask again “and what is scary (or hard) about that”? Keep going until you get to what feels like the end of the road (hint: it will have something to do with love, safety or belonging).

And then, when you get to that thought of your love, safety or belonging being threatened by this failure, start to question if that is really true. Get curious about that belief that you have (like my belief was, “my friends and family will look down on me and love me less”), and see if that’s just old programming or if it’s actually real. Play with it, get to know it, question it.

You will probably find that your worst case scenario is not as threatening to your core as you think it would be, and you may be able to relax.

And here’s the thing: the reason why doing this exercise and managing our fear of failure is so important, is because if we want to pursue the things that MATTER to us and that we really want, we WILL run into fear. So we need to know how to care for ourselves in our experience of fear. It is one more form of deep, self-care.

What do you think? Do you deal with fear of failure? If you want to share in the comments what you’re scared of failing at right now and how it’s affecting you, please do. I’ll help coach you in the comments. 

Thanks for listening, and I am so here for you.



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  1. Steph says

    Dear Jamie,

    I’m sitting here tons of miles away from you in rainy NYC in Greece, and so glad I got your email right now. It’s 2am Saturday (not raining but an almost summer-breeze coming in from the balcony) , and I kept thinking and thinking …about exactly the same thing. I couldn’t yet go to sleep…trying hard to figure things out…
    Long story short: I just quit a job I was really unhappy about, feeling that I was not meant to do it. Risked a lot, moved into a friend’s house… and I’m figuring out what I’m really meant to do. I’ve started off a project for refugee children together with some entrepreneur friends, I’m consulting a really amazing sustainability-related startup, and have tons of big ideas coming up …but with no sure and secure income at sight. Out of nowhere came a job interview for another day-job opportunity which is right in the area I want to work in and develop myself in, although my position would not give me that much creativity, freedom and responsibility I desire deep down.
    I’m very scared about how to work everything out. I know I’m feeling a deep calling for something big. I know I still have to take baby-steps and also secure my income. But I really know I don’t want anymore to work for something I don’t believe in. And I don’t know if I will get this day job and if I get it, if I’ll have the time and mind space to deal with all the other projects and ideas coming up.
    I’m very very scared to fail in all of this. In comes that I’ve been not really good to myself lately and do know I have and want to re-start to work out, nurture myself more healthily and all that. When I’m in this space of chaos and uncertainty, I fail big time in taking care of myself. Plus I feel deeply disappointed with myself when I fail to put everything together. There are just that many hours in a day…
    I have recently read the book “The War of Art” by Steven Pressfield, which talks exactly about how to deal with Resistance (capital R) . As you say, it always comes up as fear and anxiety, whenever we are up to something meaningful to us. Something we feel we are born to do. But we can’t figure out if it will workout the exact way we plan to, when and especially how.
    I know we have to surrender daily and remind ourselves that the HOW is not in our highest power. Once we face Resistance/Fear, it’s so important to see it as what it is but not believe in its stories. To recognize that it is a needed step of the journey. Every birth of something great comes with some sort of pain. That’s mother nature. That fear will try to deceive us over and over again, because it wants to keep us small, prevent us from growing. And failure, too means growing.
    Doing the work we are supposed to do in this world means doing it for the sake of it, not to seek love and recognition but to give love everyday, right into the thing we believe in and feel we are born to. Sometimes we forget it and give into this fear.
    Thank you for helping me and all the others out there to pull this around again, see it for what it is, not underestimate it, but taking over the control to take care of ourselves and guide us back to peace.
    These practical steps are much needed. Because the world needs us. Not the crazy, fearful vibes. They serve no one.
    All the best to you and all your projects ahead. You are wonderful! 🙂

    • Jamie says

      Hey Steph — thanks for sharing. That book sounds so interesting, I’ve added it to my list. It sounds like you have a ton going on and I can completely relate to the struggle to find that balance between having security but also open space to create and pursue your passions. Try to get creative with it and let yourself have just enough stability so that you’re not freaking out and stressed all the time about finances, but I would really urge you to keep time open for you to pursue that which you really want to do. Good luck and keep me posted on how things go. You’re in a really exciting time right now!

  2. Heather says

    Wow, I can relate to this so well. I have dreams of following my passions and leaving a comfortable, but not very exciting or interesting (to me) career and it all comes back to the fear of failure…1000 times over. Thank you for sharing.

  3. Melissa Jenks says

    I recently found you via Maddy Moon’s podcast, after doing Intuitive Eating for a year (and dieting and eating restrictively for 29 years before that) and I just loved the things you said during that interview. Especially regarding using pleasure as an orienting principle in your life, and completely committing to abandoning the concept of dieting, and also how so much of dieting and disordered eating really dials down to other issues of core unhappiness and feeling s of unworthiness.

    What you say here: “It all comes back to love.

    We are all scared to not be loved and accepted. ”

    More and more I find this basic principle to be true in all parts of my life. I’ve been reading about attachment theory, and how many people who struggle with depression and addiction of all kinds have insecure attachment during childhood, which leads to this constant fear that we will not be loved, we will not be accepted, and we will never be good enough. Anyway, thanks for your posts here. I also devoured your Thailand posts (I recently spent six months in southeast Asia) and I especially loved how you slowly graduated to only wanting authentic street food and no Western food after beginning by eating only at “safe” restaurants and cafes.

    So many travelers I met never got to that place! So congratulations on confronting your Western fears. To me, Thailand is such a food culture, a place where pleasure and “sanuk” (fun) are such orienting principles of life, and an amazing place to experience the joy of food and intuitive eating and movement.

    All the best!

    • Jamie says

      I’m so glad you’re here Melissa! And so cool that you spent SIX months in Asia – I am jealous! Thailand taught me a lot and it sounds like you took a lot out of your experience too 🙂

  4. April says

    Thank you for sharing your experience with failure!! I think you are spot on with needing to get to the root of why we are afraid of failure. I know for me, it’s more that if I fail that means that I’m not smart, or that my idea wasn’t good and then I feel like I wasted my time and efforts on something that didn’t benefit me. I really hate the feeling of being naive or that I should have known better. Like it makes me feel uncomfortable to type that out and read it. What I need to be better about is realizing that A- I’m human and I can’t know everything about everything, I’m going to be naive about somethings which is a good thing because then that forces me to question what I know and learn something new and B- plenty of successful people have had many failures, and say that their failures is what led them to success. I hope to get over this fear as I embark on trying to do what I really want in this world. Even if my initial idea doesn’t pan out, I’m sure that I will have learned from it and can carry that lesson with me the rest of my life. Thanks again for such an insightful post!

    • Jamie says

      April, absolutely. Your points are so right. I recently had some ideas that just flat out didn’t work and one of my friends said to me “Jamie you have NEVER done this before, why would you expect it to all work out right away?” haha… of course some of our ideas won’t work. That’s a GOOD thing – it means we are pushing ourselves to grow! Keep going, and let yourself fail. It happens to all of us 🙂 xoxo.

  5. Kassandra Baker says

    Thank you for sharing your story! I am facing the fear of failure as I start a new blog where I will be sharing my story of recovery from an eating disorder, perfectionism, and people pleasing. Eventually I would really like to travel and share my story so others don’t have to struggle as long as I did and so they will never give up. I’m 32 and have been dealing with food issues since I was in junior high.

    I feel so passionate about sharing my story and reaching out to others, but I’m afraid no one will want to listen and I will fail at being able to make this a career change. Brene Brown’s Daring Greatly has been encouraging to me as well.

    I have learned a lot from you and admire your honesty and the quality of your blog. Thank you!

    • Jamie says

      Kassandra, I felt the same way when I first started sharing my story. It was terrifying! But people are craving more REALness these days and if you can offer that to people by sharing your story, you can have a huge impact. People need to hear your truth. I know it’s so scary and let that be a part of it. But keep going, you’re up to really important things! xo.

  6. Shelly says

    Great info! I just did a lot of this with my therapist as well. I have an extreme fear of judgment – that everyone will look down on me. My therapist and I walked through kind of the same situation – going over the what if scenario. “What if a client judged you and decided to no longer work with you? Or decided to really let you have it?” It’s so uncomfortable to walk through, but it definitely opens you up to realizing some irrational fears! Thanks for this reminder to keep doing that.


This place is for you: To explore what your soul needs to hear today.

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