Fear of Rejection, Part 1: How We Accidentally Train Ourselves to Expect Failure

You’re an entrepreneur. An artist. A creator.

You have a calling so strong that you can feel it in your bones—to build a business that expresses your unique talents, interests, and purpose.

But for many of us, there’s a knot of fear and anxiety deep under all that ambition. A nagging voice that keeps telling us “this won’t work,” overshadowing our natural optimism and inspiration. These conflicting beliefs create a constant battle for control between the entrepreneur/artist/creator, and the part of us that expects to fail.

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[Full Transcript]

You’re an entrepreneur. An artist. A creator.

You have a calling so strong that you can feel it in your bones—to build a business that expresses your unique talents, interests, and purpose.

But for many of us, there’s a knot of fear and anxiety deep under all that ambition. A nagging voice that keeps telling us “this won’t work,” overshadowing our natural optimism and inspiration. These conflicting beliefs create a constant battle for control between the entrepreneur/artist/creator, and the part of us that expects to fail.

This tension between aspiration and fear creates a painful internal split that robs you of your courage and creative energy. Your enthusiasm gets washed away by the constant anticipation of disappointment, leaving you trapped between inspiration and learned helplessness.

Rather than enjoying the process—including the challenges—it takes almost all your determination to persevere through every rejection and obstacle.

Why You Expect to Fail

If any of this sounds familiar, you’re not alone. I’ve struggled with a nearly debilitating fear of failure and rejection for most of my life.

Because the nature of building a business typically involves hearing a lot more noes than yeses, it’s easy for your mind to invent limiting beliefs like “rejection = I’ll fail.”

For me, that conditioning started with a few bad assumptions about the nature of success:

“Good ideas should succeed easily. So my ideas are bad, since I fail a lot more than I succeed. Therefore my ideas don’t have value. And since I’m the source of my ideas, if they don’t have value, then I don’t have value, and I’m destined to fail.”

As a result of this fundamental error in my thinking, every rejection, every setback, every disappointment was more proof that I was destined to fail.

When you take on beliefs like “rejection = I’ll fail,” every setback actually hurts. It can feel like your entire identity is riding on every outcome. And because there’s so much at stake, you feel emotionally crushed with every rejection—further triggering and reinforcing the conditioned belief, the made up story, that “this won’t work.”

This story becomes so habitual that you rarely if ever notice yourself telling it. It lurks just beneath the surface of your awareness, something that you just take for granted as being the truth.

Ironically, your expectation to not succeed creates an attachment to a future outcome, making it nearly impossible to stay immersed in the present moment and bring your full skills and talents to the work in front of you. But these conditioned beliefs and stories are just mental habits that reinforce themselves over time—the inevitable result of mixing intense emotions with external outcomes that are out of your control.

Most big successes are built on dozens or even hundreds of failures. The visceral negative emotional experience that comes with each rejection imprints itself much more strongly in your mind than the joys associated with the occasional win. Repetition doesn’t just lead to a stronger skill. It also leads to a stronger belief, and there are few things as repetitive as failure. By constantly ping-ponging back and forth between the inevitable highs and lows of life as an entrepreneur, you can easily end up training yourself to expect the worst.

And because we’re all wired to avoid pain more than to seek pleasure, this type of default pessimism often leads to chronic avoidance and quitting. The best way to avoid disappointment is to avoid the rejections that trigger it. So your made-up stories become a self-fulfilling prophecy, a repeating loop of starting and quitting, further reinforcing your expectation of failure.

Even when you don’t quit altogether, this conditioned sense of hopelessness creates mental and emotional blockages. Rather than simply allowing your natural creative energy to effortlessly flow, you have to force yourself to stay motivated in the face of impending doom.

But fighting against these blockages is exhausting, and keeps you from creating up to your true potential as an entrepreneur. The best you can do in this state is keep nibbling around the edges—using all your effort just to get around the blockages—rather than take the consistent positive action necessary to bring your vision to life.

Seeing Through Your Made Up Story

The good news is that there’s a way to detach from this kind of fear-based conditioning and see through the stories you take for granted. But first, you need to get out of the habit of trying to cover up limiting beliefs with positive ones.

We’ve all heard that we should think of failure as learning, that every no just brings you one step closer to a yes, and that rejection is the natural byproduct of success. And yet, despite our best efforts to adopt a more positive spin on failure and rejection, many of us still struggle with our fears.

In the next post, we’ll explore why trying to reframe rejection and failure as “good” usually falls flat, and what you can do instead to finally start overcoming the fears that are holding you back.