Why Many Entrepreneurs Fear Success — and How They Can Overcome It

Do you have a fear of what it really means to get to the next level and exit the cozy blanket that is your current reality?

By Jessica Dennehy • Dec 6, 2022

Opinions expressed by Entrepreneur contributors are their own.

There's no shortage of talk about the fear of failure. It's almost a cliché topic at this point. But what about the fear of success? Picture this: You're on the road to reaching your biggest goals. It is exciting and exhilarating, but just as you come super close to attaining whatever it is you desire, you stop short. Almost on purpose. Almost as if something is restraining you, but you can't quite put your finger on it.

We all assume it's fear creeping in, preventing us from reaching new heights. What if that feeling of dread actually stems from your fear of success; a fear of what it really means to get to the next level and exit the cozy blanket that is your current reality?

Why people fear success

Successful people are no strangers to failure. Sure, it's not pleasant. But the path to success is paved with ideas that didn't go as planned or flat-out bombed. There are plenty of stories about Fortune 500 CEOs who didn't make it the first time — or the tenth. That just fuels your fire to continue trying because you know big wins come after big losses.

What really keeps you up at night is the fear of success. It's counterintuitive to think that turning your wildest dreams into reality is holding you back. When you are working so hard for something, it doesn't make sense that it is also what you fear the most.

There is comfort in being where you are now. You feel a certain level of success already, and you know that you can maintain that by simply continuing to keep doing what you're doing. However, to achieve the next level, you must leave the safety of your current position and head into uncertain territory. Success will require you to get uncomfortable in the pursuit of all those exciting things you set your sights on.

Wishing for your life to change, inviting in all the dreamy stuff — that's easy. Putting in the work to get there is another story because it requires a change in parts of your life that are difficult to maneuver.

What to do about your fear of success

To make room for all the amazingness your dream life has to offer, you need to get rid of the old stuff that will not serve you when you get there. You have to examine the details of your life now and decide what you're willing to part with. You don't anticipate that your dream life requires you to give up people, relationships and behaviors that are comfortable now. You'll have to let go of a lot of meaningful things. Those decisions can be really tough, even paralyzing. These emotions are what lead to your fear of success.

While it's difficult to rid yourself of the old you (the baggage, limiting beliefs and the opinions and energy of people who are holding you back), it opens the space you need for the new goodness you are inviting in. You can't change your life if you don't change your life! When you're starry-eyed dreaming about your future, you don't dream about the pain it takes to get there. But the pain is a necessary part of the process of transformation. It allows you an opportunity to learn more about yourself, what you want and where you want to go. It allows you the space to lean on yourself, rather than other people. And the more you embrace yourself, the more you realize that you are your own source of protection, knowledge and safety.

I learned this valuable lesson from a lobster. A lobster has a hard outer shell that keeps it safe and comfortable. The shell feels great, and with its protection, the lobster can go out into the world with little fear of being harmed. But one day, this once cozy shell starts to feel a little snug. See, the lobster started to grow ever so slightly; little by little. Suddenly, that shell doesn't quite fit the way it used to, and it feels uncomfortable. Yet, the lobster keeps growing.

One day, the lobster realizes that no matter how much the shell once felt so right, it now feels like it's a hindrance more than an asset. The lobster has to let it go in order to regain the strength and comfort that particular shell once provided. For a moment, it is vulnerable. No shell equals no protection from the outside world. The lobster braves this moment because it instinctually knows that this transformation is uncomfortable but necessary. It allows him to grow into a new shell that is more fitting for the bigger, stronger lobster it will become.

To succeed, you must evolve as well. Your former constructs won't allow you to reach the new level you're dreaming of. You have to shed the person you used to be and let go of all the stuff that no longer serves you. It's scary to walk towards the unknown half-protected. That transition state can feel unsettling — but embrace the opportunity for growth. Take that time to be alone with your thoughts, and get more in tune with who you are and what lights you up. Use this time of solitude to get clarity on what you want and who you want to become. Strengthen yourself from the inside out so you can confidently take those new, scary steps in the right direction. Your dream life is waiting.

Jessica Dennehy

Entrepreneur Leadership Network Contributor

CEO of Pivot & Slay

Jessica is a 2x best-selling author, speaker, entrepreneur & former Wall Street attorney. Through her coaching company, Pivot & Slay, she empowers entrepreneurs to embrace their CEO Power, exit their comfort zones and start taking the risks necessary for success.

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