Why We Fear Success and How to Move Forward Anyway

Why We Fear Success And How to Move Forward Anyway by Jamie Raintree | http://jamieraintree.comThe other night my husband was telling me a story in the car. To be honest, I don’t know why or how we got onto the topic. Sometimes I have to do the “smile and nod” when he’s talking about transmission repairs or header gaskets or the ridiculous things he hears on the radio on his way to work in the morning. I’m sure this story caught my attention because it was about a little girl going to school, as my babies just did. He told me she was a friends’s daughter and she was so excited about school that she got dressed up in her best dress and her favorite shoes with her hair curled and lipstick on. She was ready to take on Kindergarten!

And then she got to school and the kids laughed at her until she hid in her classroom and cried.

This story broke my heart. It brings tears to my eyes even now, just to type it. Part of me imagines something like that happening to one of my girls, which would absolutely kill me. The other part of me remembers what it was like to be that girl. Maybe for me it wasn’t because of a dress or lipstick and maybe for you it wasn’t either. But we’ve all been there. We’ve felt that little girl’s pain.

Successful People Stand Out

It starts early–the pressure to fit in. By the time we become adults, most of us have made it an art not to stand out in a crowd. We don’t want to look like the loser in any group, but one thing that most of us don’t talk about, or maybe don’t even realize, is that we don’t necessarily want to be the winner either. Well, we do, but only if no one looks at us while we do it. Because while we all know we’ll be on the receiving end of ridicule if we don’t have it all together–if we fail–we also worry we’ll get ridiculed if we’re the most put together one in the room–the one people envy, and therefore, try to tear down.

Like that poor little girl.

I feel the fear acutely and I know many writers do too, if not most. How many times I’ve heard a newly published author–one of the few who have beat the odds and gotten a Big 5 deal–APOLOGIZE for “having to” put themselves and their books in front of people. It doesn’t matter that they’ve worked years, had their writing torn to shreds dozens of times, and put pen to paper many mornings after sleepless, tearful nights. They’ve earned their success and yet they are still afraid to own it. I’ve heard NYT bestselling authors tell others and themselves that their success was a fluke that had nothing to do with creating a beautiful book people loved to read. If success is an accident, or a random stroke of good luck, it’s less threatening.

We suffer from underdog syndrome.

Underdog Syndrome

Think about every sports movie you’ve ever seen. One the one hand, we have the main characters. The underdogs. We love them because they’re quirky. They’re honest. We see their insecurities and they remind of us ourselves. We want to root for them even though, or maybe because, they’ve never won a game in their lives.

On the other hand, we have the champions. The ones who have won every year and who have fancy matching uniforms. How are they portrayed? To put it bluntly, they’re the assholes. They’re the ones who taunt, belittle, prank, and generally make the underdog’s life a living hell. Sure, often times, they get the opportunity to redeem themselves when they see the error of their ways, but mostly we still just hate those guys.

In our minds, they are the CEOs who make billions but don’t pay their taxes. They’re the corporations who treat us like a number. They’re the popular kids who wouldn’t let us sit at their table in the cafeteria. At least, that’s how we see them. And whether or not any of this is accurate information, we know one thing: we don’t want to be like them.

And all this would be okay if, deep down, we didn’t actually want to be successful…if these perceptions weren’t holding us back, causing us to get in our own way.

Ahem…speaking from experience.

Becoming One of Them

With all of those negative connotations associated with success, is it no wonder we fear losing our humility? Losing our friends who are suffering with their struggle so much that they can’t be happy for us? Wondering if we’ll still be ourselves on the other side? These fears can be debilitation if we let them. They can stop us from taking the leap toward what our heart most desires. Or, we can answer follow the path we know we’re meant to lead.

Here are some things that have been helping me move forward:


Instead of zeroing in on and lamenting about the successful people who seem arrogant, selfish, or who always put on a perfection facade, start looking at the ones who are compassionate, supportive, and who allow people to see their real side. Start to believe that success and humility don’t have to be mutually exclusive. (Jen Hatmaker is the epitome of this for me.)


If you surround yourself with people who are further along in the journey than you, you will create a support system full of people who will be thrilled to see you reach their level. They will be able to show you how to get there, and they will prove that successful people are still just people–every single one of us has our flaws and our strengths.


These fears are programmed into us by society, by our parents, by our friends. But that quiet voice you hear speaking underneath the loud noise that says you deserve more than where you are now–that’s the real you. Teach yourself to ignore anything that isn’t the real you.


Overcoming fears, especially such deep-seeded ones, is a long process. It’s one that requires daily steps in the right direction. Maybe you don’t send out twenty query letters today (maybe you do), but maybe you write the first paragraph and promise yourself you’ll write the second one tomorrow. Small steps add up and they help you build the confidence to believe you deserve the big rewards when you get there.


Compliments aren’t handed out easily so when someone goes out of their way to tell you how much they love your work or how much faith they have in you reaching your goals, believe them. They wouldn’t say it if they didn’t mean it. Try to see your value through their eyes. (I can’t miss the opportunity here to thank the people who have done this for me. You keep me going more than you know.)

Do you fear success? Why do you think that is? How do you work to overcome it?

I am an author and a writing business teacher. I am also a mother of two, a wife, a businesswoman, a nature-lover, and a wannabe yogi. My debut women's fiction novel, PERFECTLY UNDONE, will be released on October 3, 2017. Here, I blog about my journey in publication in the hopes of inspiring others to follow their own dreams.

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