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$50M Woman: How She Overcomes Fear And Failure

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Fear and failure. Like the toy prize found in a box of Cracker Jacks, these two words just come in the box labeled entrepreneurship.

But what are the best kept secrets on how to overcome these paralyzing words?

Kelsey Ramsden has the answers.

As Founder and owner of four companies, Ramsden is set to bring in revenues of $50 million this year. She is Canada’s Top Female Entrepreneur two years in a row, a select member of EY’s Winning Women Entrepreneurs, and on the Richard Branson Centre for Entrepreneurship as a mentor.

In this follow up article to her 8 Simple Tips From A $50M Female Entrepreneurshe provides guidance on how to overcome fear, what to do when you fail and one tactic to keep you going when you want to quit;

How To Overcome Fear

1. Imagine The Worst Thing That Can Happen

Smart entrepreneurs ask themselves what’s the worst thing that could happen if they do fail. They play it out. Imagining the worst case scenario and asking themselves if they could handle the answer. For example, if I were to fail for some reason with our Academy, my only setback would be a bruised ego and the need to start another business. Okay, can I handle that? Yes -- I can. Ramsden says; “Turn the light on when the monster is in the room. You’ll find it’s not as scary as you think.”

2. Attach Yourself To The Process -- Not The Outcome

Entrepreneurs get fixated on a certain outcome. We want success -- whatever that looks like for each of us. However, Ramsden says; “Getting too attached to the outcome is what gets people really down. If you do, you’re bound to have a lot more grey days than sunny ones.” So what to do instead? Focus on the ‘practice of business’. Mighty Wise Academy member and entrepreneur Arturo Monge, Founder and CEO of Finanza Pro, put it best; “Much more productive mindset to think I need to practice business everyday, than putting a huge amount of pressure on myself thinking I need to build a successful business in x amount of time.”

3. Mitigate Potential Risk Ahead Of Time

Following on the back of imagining the worst case scenario, Ramsden thinks entrepreneurs should mitigate risk and prepare for the potential outcome ahead of time. “It’s like a business prenup with myself. I want to fight with myself now before things go bad. Then I’m ready if the tide starts to turn that way because I’m both prepared for it and willing to accept it.”

What To Do When You Fail

4. Count It As Tuition For Learning

Investment in ongoing education is key. So when entrepreneurs fail, one approach is to count failure as a tuition payment for learning and growth. Ramsden admitted “it doesn’t make it fun, but it’s still paid learning toward a better business. My loss is counted as learning something now versus 15 years from now when it would cost me ten times as much. It’s my tuition payment for that education.”

5. Don’t Attach Yourself To It

You are not your failures. You are you. After listening to Ramsden explain “they are my failures, but they aren’t me”, Academy member and entrepreneur Irina Alionte, Founder and CEO of Born2Succeed, restated it best; “So many times we identify ourselves with our business. But you have to realize your failures do not define you. They are not who you really are.” Don’t attach yourself to your times of failure. Wise entrepreneurs let go and move on.

6. Ask Yourself Was It My Ability Or Application?

When entrepreneurs fail, it really comes down to two reasons (other than events you cannot control); you either lacked the ability to pull it off, or you had the ability, but failed in your application (execution). Ramsden shared a story; “I failed to save a joint venture that went utterly sideways and wound up in court. So I asked myself if I lacked the ability or did I fail to apply my ability the right way. And frankly it was probably my ability at the time to negotiate a proper joint venture agreement.”

7. Don’t Worry What Other People Think

Standout entrepreneurs don’t care what others think (except caring about what customers think.) Steve Jobs is a classic example -- especially after he was fired from Apple originally but then came back to save the company. He never really cared what others thought of him. Ramsden adds to this; “You may fail at something, or something may go wrong, but two years from now, five years from now, nobody remembers and no one cares. It’s replaced by all the new things you’ve done since.”

Bonus: What Can Keep You Going When You Want To Quit

Ramsden had it rough in the beginning. Listen to this:

Kelsey Ramsden: “The thing that kept me so focused and motivated at the start was proving it to myself. I had a lot of naysayers because I never was good at all the traditional boxes you would check as a woman.”

Eric Wagner: “It sounds like you had a chip on your shoulder.”

Ramsden: “I would say yes, I did.”

Wagner: “Hearing people tell you it can’t be done. You’re crazy. You’re a woman. You don’t know what you’re doing in the construction business. So your little voice is saying ‘watch me’, right?”

Ramsden: “Absolutely. I wanted to prove to myself that I could do it and that’s what kept me going.”

"Watch me" is a powerful motivator when you’re ready to quit. I remember using it for many years when I started my own entrepreneurial path. People thought I was nuts to drop out of college to start my first business and all I could think was “yeah, watch me.”

Seven great points from Ramsden on how to overcome fear and failure as an entrepreneur. Which one resonates with you?

NOTE: I'm Eric. Life-long entrepreneur and Founder of Mighty Wise Academy. If you'd like to learn more of what it takes to become a successful entrepreneur, you can connect with me here.

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