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Fear of Failure Versus Fear of Success

You want to start that new business you’ve been dreaming about, go after a big client, or make a leap into the unknown…but something is holding you back. It’s scary sh*$! I know at every transition in my entrepreneurship journey, I’ve felt it: fear. But what are you actually afraid of? Is it a fear of failure, or is it really fear of success? I’ve found that taking a look at my fearful thinking and understanding what drives it can take the power out of it. Oftentimes, when I dig deep, I find that I am more afraid of success than failure. Rising to new levels in my business and life is scary, because it’s the unknown! Here’s my insights on fear of failure versus fear of success, plus how to overcome these fears and start taking action on your dreams. 


“Fear keeps us focused on the past or worried about the future. If we can acknowledge our fear, we can realize that right now we are okay.” – Thich Nhat Hanh

Fear of Failure 

Everyone has failed at something before. You’ve messed up, struck out…lost a job, a relationship, or a business deal. Failure is a known entity, and it doesn’t feel good. Fear of failure stems from not wanting to experience the pain and shame of something not working out. Having our hopes and expectations dashed. Not getting what we want. Hellooo perfectionism! It can stem from a delusion that successful people have never failed. 


The reality is, anyone who’s made it has failed many many times. They just didn’t let failure prevent them from trying again. It’s all about perspective. They came to see failure as a learning opportunity rather than something to beat themselves up over. 


I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed. — Michael Jordan 


What would happen if the next time you made a mistake or messed something up, you didn’t shame or blame yourself? What if you patted yourself on the back and said, “good effort! I’m proud of you for taking this risk. That was brave. Now, what did you learn from this experience? “

Fear of Success 

Success is about achieving something new or different than what we’ve got. It’s about entering uncharted territory. Playing in a bigger sandbox. Growing into the 2.0 version of yourself. It’s about change and the unknown. Notably, fear of the unknown is one of the most fundamental fears of being human. Which is how failure, which is often more comfortable and familiar to us, can feel like the cozy safe option. 


Fear of success can rub up against our beliefs about ourselves. Our feelings of worthiness. We think we really really want something…but deep down, do we truly believe we are deserving of it? This can be an uncomfortable question to answer. 


I’m going to tell you a little story of confronting my own fear of success…

Some of you who know my story know that I had a pretty tough upbringing. Eventually, my sister, brother and I were sent to Mooseheart School in Illinois because our family couldn’t properly take care of us. I remember my dad having very negative fixed beliefs about people with money. They were assholes. He had a big chip on his shoulder and alot of blue collar pride, and venom in his thoughts.  How things are handed to those with money, they do not really work etc…


But the thing was, I’d forgotten about all this. I was in my thirties with three kids and running my own business. Although I had done very well, I couldn’t seem to break through a certain point (financially). There was always something holding me back from reaching my earning goals. What was going on? I decided to go back to the past and take a look at my history around money, work, and success. That’s when I discovered my dad’s voice in my head. 


“You don’t want to be too big for your britches…” “Success and money change you…” “Money is evil…” “You don’t want your kids to be spoiled brats…like people who grew up with a silver spoon in their mouth…”


A Realization 

My fear of success stemmed from not wanting to spoil my kids so they’d grow up into rich jerks. I wanted them to understand how to earn shit and not expect things to just be given to them. I wanted them to develop character and grit and know where we came from.  Appreciate the process, and the outcome, instead of it being handed to them.

I was holding myself back from earning more money because I didn’t want to spoil my kids…and I had old negative beliefs around people who made money. That they weren’t my people. That being successful and making more money would change me in a bad way, too. 


Doing the self work, I realized how false these beliefs were. I could make good money and not spoil my kids. Just because I grew up poor, and told money was evil, doesn’t mean that was where the fight and drive could ONLY come from. Success could help me grow into a better person, someone that could help others. I was in charge of my own destiny! I could build the life I wanted. I was no longer stuck like I was when I was a kid. This was a powerful realization.


Do the thing you fear to do and keep on doing it… that is the quickest and surest way ever yet discovered to conquer fear. – Dale Carnegie


After doing this work, things began to shift for me. I began to feel more comfortable with earning more and succeeding in my business. Slowly, I began to reach my earning goals. But the growth never ends. It’s lifetime work. 


Facing Your Fears

Today I’m in a much different place in my entrepreneurship journey than I was back then. Working as a business coach, living as a digital nomad, each of these transitions and changes bring up the fear of success and new opportunities to work through it and learn more about myself. As a coach, I love helping my clients and other coaches do this work, too. I’m grateful for my experiences because they enable me to help others. 


The advice I give to my clients to overcome fear of either failure or success is to first look for the root of your fear. Go back in time and see where it comes from. Practice awareness and willingness to let these old limiting beliefs go. Surround yourself with a support network of people who will encourage you to face your fears, rather than feed them. Don’t wait to feel unafraid to take action. Take action, despite feeling the fear. For every big leap I’ve made I have never felt entirely ready. 


Do you struggle with fear of failure or success? Do you need support to work through limiting fears that are holding you back in your business? I can help! Contact me to schedule a free coaching consultation. 


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