Wholehearted Coaching

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Failure: how to overcome our biggest fear | ep 130


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Do you remember that phrase: “Failure is not an option”? Yeah, that’s a lie, love.

The truth is failure is definitely an option. In fact, failure is the ONLY option. If you have big dreams and want to do big things in this world, you need to become friends with failing.

In this podcast episode, I talk all about navigating our fear of failure in a healthy way (and you can listen at the link above or by clicking here). Keep reading if you want to learn my three F’s of failure and how to really make failing work for you.

As a life coach, I work with people who have some pretty big dreams and goals and visions. And I bet that’s you, too, love, because the Wholehearted Community is made up of some pretty incredible dreamers. And so often when we have an incredible dream and it means so much to us, we find ourselves delaying and we don’t understand why.

So, we start to become really judgmental. We start to feel ashamed. We start to feel all of the guilt associated with not doing the right thing.

Then we start to think that we just need to be fixed. That we need some sort of five-step plan, or a schedule, or a calendar to accomplish this goal.

But love, that’s not the problem. The problem is simply that you are afraid.

Maybe you’re afraid of judgment, of uncertainty, that you’re not good enough. Or maybe you’re feeling the biggest fear of them all — that you are going to fail.

The more something means to you, the scarier it will feel.

The more something means to you, the more reasons you have to be afraid.

If this is you, if you have been procrastinating or telling yourself that you’re lazy, a mess, a failure, or any of the above… you’re just scared. You’re scared of this thing you just love so much not working.

You don’t need to fix some character flaw within yourself. You don’t need the next best calendar or someone’s pre-made schedule. You just need to learn how to navigate failure.

Now, I know: it’s easier said than done. But today, I’m going to give you tangible ways to overcome that fear of failure, navigate that fear, and reframe what failure is.

We have been sold a lie

We have been told that one of the worst things you can ever do is fail. To go after something you really want and have it not happen. So, we associate failing, making mistakes, and not getting it right with some of the worst things possible.

I want you to think of the first words or feelings that come up for you when you think of failure.

Here are a few journal prompts to help you out:

  • People who fail are…

  • In my household, failing was…

  • When I think of failing, I feel…

  • If I fail, that means that…

Allow yourself to reflect on what it felt like to answer those prompts doing so with curiosity over judgment. What came up for you?

Maybe some things were a little challenging. Maybe they’re words and feelings you associate with being negative, with things you don’t want.

With this belief, what we tend to do is navigate our lives trying to avoid failure. But, in our pursuit to not fail, we don’t do the things we really want to do. And love, not going after the things you truly want is far worse than failing.

We have to learn that the opposite of failure isn’t success.

The opposite of failure is never trying.

Scientists have a different word for failing

Scientists call failure “data.” They understand that in order to solve a problem, to reach a cure, to achieve something they really want, they have to conduct hundreds, maybe thousands of experiments. Each one of those experiments isn’t a failure. Is just data. It’s giving them more information about what they need to do next. So, the next time they try, they do it differently and armed with greater awareness.

It’s said that Thomas Edison failed 1,000 times before inventing the light bulb. In an interview, he was asked, “What was it like failing 999 times?” To which Edison responded, “I didn’t fail 999 times. The light bulb was an invention with 1,000 steps.”

And so it is with our own dreams and goals, love. I can’t begin to tell you the amount of “failures” and mistakes that I have made in creating Wholehearted Coaching. I seriously can’t begin to count them! But I can tell you that each one of them has given me insight that has gotten me to the successful coaching business and dream life that I know today.

But let’s also be real. It’s not like in failing and making those mistakes, I was happily thinking, “Oh, I’m learning so much!” No. It sucks. It really hurts when we fail. But, you understand that those mistakes are a sign that you are trying.

If we live a life where we make no mistakes, we stay exactly where we are. But, I get it — if we make mistakes, it feels so uncomfortable. So, we have to become more comfortable with the uncomfortable, love.

How to become comfortable with failing

I want to share with you my Three F’s of Failure, also known as my Fail Better Action Plan.

Feel the Feels

Oftentimes, we think we just have to move on after failing. That we need to get over it or suck it up. We’re taught that there is no space or time to process our feelings because we have to keep going after our goals. While this is well-meaning advice, it’s harmful to us.

If we don’t process the pain and feelings of failure, they with us.

I once heard emotions described as “energy in motion.” Keeping that in mind, picture your feelings of failure as energy moving through you that, if not channeled properly, manifests in really destructive ways. It can cause us to lash out at others, to get angry at ourselves, to say unkind things to ourselves.

What you need to know is that you are allowed to have feelings about failing. So, give yourself the time and space to properly feel the feelings.

Now, while some of us try to run from or avoid the feelings, others become overly identified with them ruminating and obsessing over the failure. Sometimes, you may be a mix of both. In these moments, we have to understand that while this is a really disappointing moment, it is simply a moment. It is a circumstance we find ourselves in. It is not who we are.

So, with Feel the Feels, I’m asking you to tap into compassion and here are 2 guiding questions to ask yourself when you find yourself being really unkind and not feeling the feelings:

  • What would a loving friend or family member say to me in this moment?

  • What would a loving friend or family member do for me in this moment?

Figure out what those things are and try to see if you can reciprocate them for yourself.

Find the Growth

In this step, be sure to take your time. It’s important to process your feeling before trying to find the wisdom and growth. Sometimes, you’ll find it in a matter of minutes, hours, or days. Sometimes, it takes longer. Allow yourself to take that time.

There’s no need to rushing to the silver lining. Be patient. Honor the timeline. Honor the process. The wisdom will come.

Fail. A lot.

You’re probably like, “Whaaaat?? You want me to fail, Shirin??” Yes! Failing is really important for 2 reasons:

  1. You’re never going to become desensitized to failure. It’s always going to suck in some way. But, the more you fail, the more you learn that it isn’t always as painful as you imagine. And, if it is, you’re going to show yourself that you know how to handle it.

  2. You’re going to come to understand that failure just means that you are trying, love. It means that you’re one step closer. That the next step you take, could be the one.

I want to challenge you to fail this week.

Find something that you know you know you may not do right, that you may make a mistake on and I want you to try that thing. Do it and see what happens. See if you can apply the Three F’s.

I want to leave you with this beautiful quote by Adrienne Maree Brown:

If you tell a story without the mess and failures, I don’t trust the success and lessons.

If you hide your mistakes, you’ll never be known.

Everyone makes mistakes.

What matters are the steps you take to learn the lessons.

Be humbled. Laugh. Stay in your dignity and make new mistakes.


Did you know that each podcast episode comes with free guided journal prompts?

If you want to be in the know and get each Mindset Monday straight to your inbox complete with journal prompts to take you even further, get on my email list.


If you enjoyed this, you’ll also enjoy these posts & podcast episodes:

Self Compassion vs Self Criticism: Failure is a necessary part of creating our dreams. But let’s be honest, it is painful. So often, the source of that pain comes from ourselves. Listen to this podcast episode to learn how you can be more forgiving and kind to yourself on the other side of failure so you can keep making the mistakes that will take you where you want to be.

How to navigate fear: Our biggest dreams also hold our biggest fears. That’s why most of us delay taking the next step towards our dreams. It’s not because we’re lazy or procrastinators but because we’re just really scared. Listen to this episode to learn what fear is, how to navigate your fear, and how to unlock the path to your biggest dreams.

What’s worse than failure: Our fear of failure is often what holds us back from doing the things we want to do. However, there is something far worse than failure — never trying. Listen to this episode to learn how to fail bettter.


About your host, Shirin Eskandani

Hi, love! I’m Shirin.

Coach, speaker, writer, and life alchemist.

I teach you how to listen to your intuition again, tune out all the BS, and let your heart lead the way.

Because once you strengthen your inner GPS, decisions become easier, boundaries become clearer, and belly laughs become a daily thing.

A LITTLE BIT ABOUT ME:

  • I’m a certified life coach (accredited through the International Coach Federation)

  • My husband and I met on Instagram and we live in Brooklyn, NY with our plant babies 

  • I have a masters degree in Music and was a professional opera singer for twelve years.  I worked all over the world singing on stage at Carnegie Hall and the Metropolitan Opera (more on that later…). 

  • I believe in the woo just as much as I do the work (internal and external).  No amount of crystals and affirmations will make up for a lack of a healthy mindset and aligned action.

  • I love all the Real Housewives franchises.  Don’t make me choose one… seriously, don’t.


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