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Why Having a Win-or-Lose Mindset Will Kill Your Entrepreneurial Dreams Business risks are a necessity, and the greatest roadblock to taking action is having a win-or-lose mindset. Try to shifting to a win-or-learn mindset instead.

By Jessica Dennehy

entrepreneur daily

Opinions expressed by Entrepreneur contributors are their own.

Fear of failure is the number one thing holding most people back from making the moves necessary to change their lives. In business, most entrepreneurs are apprehensive about their next move. Their fear of failure immobilizes them as they overanalyze every angle or possible outcome. They become so paralyzed that they avoid making any moves. They actively choose the path of least resistance, avoiding the risk entirely.

Being risk-averse as a business owner comes at a great cost. While you wait it out in fear, your opportunity is passing you by. The cost of inaction is that you never evolve. You never learn the lessons necessary to create the success you desire. Entrepreneurs are afraid to fail by taking a risk; but the real failure is standing still. Inaction is failure. Mistakes are merely lessons.

Related: The Greatest Risk Is Taking No Action, Says This Military Vet Entrepreneur

From win-or-lose to win-or-learn

Business risks are a necessity. The greatest roadblock to taking action is having a win-or-lose mindset. When you focus on what you have to lose, the choices become more difficult. You are forecasting a 50% chance of failure rather than highlighting all the new opportunities you can potentially gain from taking the risk! Focusing on the negative creates fear and an inner dialogue that tells you the odds of failure are too high to be worth it. You are afraid to lose time, money or clients, and the sting of that potential loss makes you hesitate to move forward.

Try this instead: Approach every new endeavor with the mindset that you will either win-or-learn. In other words, you will try something new and succeed — or you will fail but learn a lesson, so you can try again with a greater chance of success.

Every successful person has scraped their way to the top with trial and error. Everyone has lost something valuable at one point or another. That loss does not define you. Pivot your perspective to believe that if you make a mistake, it's not a failure; it's a learning experience. The more you learn, the more you grow, and the easier it is to succeed on the next attempt. When you face each issue with a win-or-learn mindset, you have a 100% chance of a positive outcome.

I'm not a natural risk-taker. As a former Wall Street attorney, I was risk-averse, always preparing for the worst-case scenario and helping others avoid risk at all costs. When I took the leap into entrepreneurship, I needed to pivot my mindset. I invested the last of my savings into a startup business. It was scary! I consider it almost miraculous that I took such an enormous risk to open a unique, niche business. This was my first real lesson in a win-or-learn mindset, and it was a perfect example of what is possible when you let go of fear and are willing to take action.

Related: 8 Reasons Failure Makes You a Better Entrepreneur

The risk of playing it safe

Everyone thought I was crazy for leaving my safe and comfortable career. But I saw the opportunity to create a more aligned life of freedom. I swapped out my fears of failure for the vision of limitless possibilities with this new (but scary) opportunity to start my own business. Yes, it meant I could lose money and the safety net of my corporate job, but the reward of freedom and success was worth the risk. I knew I'd either win … or learn a tremendous lesson.

Now here I am, a decade later, still taking risks and slaying it in business. I continue to push myself out of my comfort zone to achieve higher levels of success. I realized that overanalyzing choices instead of taking action will kill your business (and your dreams) faster than anything else. The fact is that even a wrong decision will lead to learning and growth. This realization gives me the confidence to take decisive action again and again. With each new risk, I gain more experience, knowledge and wins.

If I had played it safe 10 years ago, I would still be stuck at a dead-end corporate job living a mediocre life. I wouldn't be a best-selling author, own four businesses, have limitless income and be on a beach at 2:00 p.m. most days. I get to live life on my terms, work on my terms and create a legacy for myself and my family that is far more valuable than any cushy corporate salary.

Related: Get Out of Your Comfort Zone, Take Risks and Run With the Big Dogs

That all happened because of my willingness to nurture my ability to check my ego at the door and realize that actual failure is remaining paralyzed by fear. Playing it safe will keep you from achieving all the amazing things you truly desire. By adopting a win-or-learn attitude, you will be able to go after the opportunities that will catapult you towards success. It may be scary to take the big risks you need to find great success, but it's even scarier to remain in your comfort zone without any forward motion.

The choice is yours. You can stand still for all eternity playing it safe. Or you can get out there and slay your way to freedom, alignment and growth.

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.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

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